MILE / Metromile Inc - SEC Filings, Annual Report, Proxy Statement

Metromile Inc
US ˙ NASDAQ ˙ US5916971071
THIS SYMBOL IS NO LONGER ACTIVE

Basic Stats
CIK 1819035
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Metromile Inc
SEC Filings (Chronological Order)
This page provides a complete, chronological list of SEC Filings, excluding ownership filings which we provide elsewhere.
August 8, 2022 15-12G

As filed with the Securities and Exchange Commission on August 8, 2022

As filed with the Securities and Exchange Commission on August 8, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

August 3, 2022 S-8 POS

As filed with the Securities and Exchange Commission on August 2, 2022

As filed with the Securities and Exchange Commission on August 2, 2022 Registration No.

July 28, 2022 10-Q/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q/A (Amendment No. 1) (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 ☐ T

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q/A (Amendment No.

July 28, 2022 EX-3.1

Certificate of Formation of Metromile, LLC.

Exhibit 3.1 CERTIFICATE OF FORMATION OF METROMILE, LLC Dated as of July 28, 2022 This Certificate of Formation of Metromile, LLC is being duly executed and filed by the undersigned, as an authorized person, to form a limited liability company under the Delaware Limited Liability Company Act (6 Del. C. ? 18-101, et seq.). 1. Name. The name of the limited liability company formed hereby is Metromile

July 28, 2022 EX-3.2

Amended and Restated Limited Liability Company Agreement of Metromile, LLC.

Exhibit 3.2 AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT of METROMILE, LLC This AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT (this ?Agreement?) has been adopted by the members of the Board of Managers (the ?Board of Managers?) of Metromile, LLC, a Delaware limited liability company, f/k/a Citrus Merger Sub B, LLC, (the ?Company?), effective as of July 28, 2022. WHEREAS, the

July 28, 2022 EX-99.1

Lemonade Completes Acquisition of Metromile In return for under $145 million in stock, Lemonade receives over $155 million in cash, over $110 million in car premiums, an insurance entity with 49 state licenses, and precision data from half a billion

Exhibit 99.1 Lemonade Completes Acquisition of Metromile In return for under $145 million in stock, Lemonade receives over $155 million in cash, over $110 million in car premiums, an insurance entity with 49 state licenses, and precision data from half a billion auto trips July 28, 2022?Lemonade (NYSE: LMND), the insurance company powered by AI and social impact, today announced the closing of the

July 28, 2022 10-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A Amendment N0. 1 ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 ☐ TRANSITION REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A Amendment N0. 1 ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39484 METROMI

July 28, 2022 8-K

Changes in Control of Registrant, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Material Modification to Rights of Security Holders, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Financial Statements and Exhibits, Completion of Acquisition or Disposition of Assets, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 28, 2022 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File Number) (I.R.S. Employ

June 14, 2022 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 14, 2022 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File Number) (I.R.S. Employ

May 31, 2022 SC 13D/A

MILE / Metromile Inc / Magnetar Financial LLC - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D. C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 1)* Metromile, INC. (Name of Issuer) Common Stock, par value $0.0001 (Title of Class of Securities) 591697107 (CUSIP Number of Class of Securities) Alec N. Litowitz Magnetar Capital LLC 1603 Orrington Ave. Evanston, Illinois 60201 (847) 905-4400 (Name, Addr

May 10, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 10, 2022 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction of Incorporation) (Commission File Numbe

May 10, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 ☐ TRANSITION REPORT PUR

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File No.

May 10, 2022 EX-99.1

Metromile Announces First Quarter 2022 Results SAN FRANCISCO, May 10, 2022 -- Metromile, Inc. (NASDAQ: MILE, MILEW), a leading digital insurance platform and pay-per-mile auto insurer, today announced its results for the first quarter ended March 31,

Metromile Announces First Quarter 2022 Results SAN FRANCISCO, May 10, 2022 - Metromile, Inc.

March 22, 2022 424B3

Up to 50,828,643 Shares of Common Stock Up to 7,846,666 Shares of Common Stock Issuable Upon Exercise of Warrants Up to 180,000 Warrants

Filed Pursuant to Rule 424(b)(3) Registration No. 333-253055 PROSPECTUS Up to 50,828,643 Shares of Common Stock Up to 7,846,666 Shares of Common Stock Issuable Upon Exercise of Warrants Up to 180,000 Warrants This prospectus relates to the issuance by us of an aggregate of up to 7,846,666 shares of our common stock, $0.0001 par value per share (?Common Stock?), which consists of (i) up to 180,000

March 11, 2022 POS AM

As filed with the Securities and Exchange Commission on March 11, 2022

As filed with the Securities and Exchange Commission on March 11, 2022 Registration No.

February 28, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 28, 2022 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction of Incorporation) (Commission File

February 28, 2022 EX-99.1

Metromile Announces Full Year and Fourth Quarter 2021 Results SAN FRANCISCO, February 28, 2022 -- Metromile, Inc. (NASDAQ: MILE, MILEW), a leading digital insurance platform and pay-per-mile auto insurer, today announced its results for the fourth qu

Metromile Announces Full Year and Fourth Quarter 2021 Results SAN FRANCISCO, February 28, 2022 - Metromile, Inc.

February 28, 2022 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 ☐ TRANSITION REPORT PURSUANT TO SECTI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39484 METROMILE, INC. (Exact na

February 28, 2022 EX-4.3

Description of Securities.

Exhibit 4.3 DESCRIPTION OF SECURITIES Metromile, Inc. (?we,? ?our,? ?us,? or the ?Company?) has two classes of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the ?Exchange Act?): common stock, par value $0.0001 par value per share (the ?Common Stock?), and public warrants, each whole public warrant exercisable for one share of Common Stock at an exercise

February 14, 2022 EX-99.2

JOINT FILING AGREEMENT

Exhibit 99.2 JOINT FILING AGREEMENT The undersigned agree that this Schedule 13G dated February 14, 2022 relating to the common stock, par value $0.0001 per share, of Metromile, Inc. shall be filed on behalf of the undersigned. INTACT FINANCIAL CORPORATION By: /s/ Fr?d?ric Cotnoir Name: Fr?d?ric Cotnoir Title: Executive Vice President and Chief Legal Officer INTACT VENTURES INC. By: /s/ Fr?d?ric C

February 14, 2022 SC 13G/A

MILE / Metromile Inc / Intact Financial Corp - SC 13G/A Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* Metromile, Inc. (Name of Issuer) Common stock, par value $0.0001 per share (Title of Class of Securities) 591697107 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to whi

February 14, 2022 SC 13G/A

MILE / Metromile Inc / Nantahala Capital Management, LLC - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* METROMILE, INC. (Name of Issuer) Common Stock (Title of Class of Securities) 591697107 (CUSIP Number) December 31, 2021 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedul

February 14, 2022 SC 13G/A

US5916971154 / MetroMile, Inc. / Index Ventures V (Jersey), L.P. - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1)* Metromile, Inc. (Name of Issuer) Common Stock, $0.0001 par value per share (Title of Class of Securities) 591697115 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule p

February 14, 2022 EX-99.1

JOINT FILING AGREEMENT

EXHIBIT 99.1 JOINT FILING AGREEMENT Each of the undersigned, pursuant to Rule 13d-1(k)(1) under the Act, hereby agrees and acknowledges that only one statement containing the information required by Schedule 13G need be filed with respect to the ownership by each of the undersigned of the Common Stock and the information required by this Schedule 13G, to which this Agreement is attached as an exhi

February 4, 2022 SC 13G/A

MILE / Metromile Inc / WELLINGTON MANAGEMENT GROUP LLP - SEC SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1 )* Metromile, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 457821106 (CUSIP Number) December 31, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which this Schedu

February 2, 2022 8-K

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 2, 2022 (February 1, 2022) METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction of Incorporation)

February 2, 2022 EX-99.1

Metromile Announces Stockholder Approval of Merger Agreement with Lemonade Transaction Anticipated to Close During Q2 2022

Exhibit 99.1 Metromile Announces Stockholder Approval of Merger Agreement with Lemonade Transaction Anticipated to Close During Q2 2022 SAN FRANCISCO, February 1, 2022 ? Metromile (NASDAQ: MILE, MILEW) (the ?Company?), a leading digital insurance platform and pay-per-mile auto insurer, announced that at the Special Meeting of Stockholders held today, the Company?s stockholders approved a proposal

February 2, 2022 425

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 2, 2022 (February 1, 202

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 2, 2022 (February 1, 2022) METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction of Incorporation)

February 2, 2022 EX-99.1

Metromile Announces Stockholder Approval of Merger Agreement with Lemonade Transaction Anticipated to Close During Q2 2022

Exhibit 99.1 Metromile Announces Stockholder Approval of Merger Agreement with Lemonade Transaction Anticipated to Close During Q2 2022 SAN FRANCISCO, February 1, 2022 ? Metromile (NASDAQ: MILE, MILEW) (the ?Company?), a leading digital insurance platform and pay-per-mile auto insurer, announced that at the Special Meeting of Stockholders held today, the Company?s stockholders approved a proposal

January 24, 2022 SC 13G

MILE / Metromile Inc / Man Group plc Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No.)* Metromile, Inc. (Name of Issuer) Common Stock, par value $.00001 per share (Title of Class of Securities) 591697107 (CUSIP Number) January 14, 2022 (Date of Event Which Requires Filing of This Statement) Check the appropriate box to designate the rule pursuant to which

January 21, 2022 425

Filed by Metromile, Inc.

Filed by Metromile, Inc. Pursuant to Rule 425 under the Securities Act of 1933, as amended and deemed filed pursuant to Rule 14a-6 under the Securities Exchange Act of 1934, as amended Subject Company: Metromile, Inc. (Commission File No. 001-39484) I still haven?t received any information for the upcoming vote. I reached out to the email provided in the FAQs last week, but still haven?t received

January 21, 2022 8-K

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 21, 2022 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction of Incorporation) (Commission File N

January 21, 2022 425

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 21, 2022 METROMILE, INC.

425 1 ea154261-8k425metromile.htm CURRENT REPORT UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 21, 2022 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other

January 20, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement. ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)). ? Definitive Proxy Sta

January 13, 2022 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement. ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)). ? Definitive Proxy Sta

December 29, 2021 DEFM14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) Information Required in Proxy Statement Schedule 14A Information Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 ? SCHEDULE 14A (RULE 14a-101)? ? Information Required in Proxy Statement Schedule 14A Information Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? ?

December 28, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 23, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction of Incorporation) (Commission File

December 17, 2021 425

2

Filed by Metromile, Inc. Pursuant to Rule 425 under the Securities Act of 1933, as amended and deemed filed pursuant to Rule 14a-12 under the Securities Exchange Act of 1934, as amended Subject Company: Metromile, Inc. (Commission File No. 001-39484) How will EBS be included in the conversations going forward? // What will happen to EBS? We are looking to create the greatest opportunity for the EB

December 16, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 13, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction of Incorporation) (Commission File

December 13, 2021 SC 13D

MILE / Metromile Inc / Magnetar Financial LLC - SCHEDULE 13D Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D. C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. )* Metromile, Inc. (Name of Issuer) Common Stock, par value $.00001 (Title of Class of Securities) 591697107 (CUSIP Number of Class of Securities) Alec N. Litowitz Magnetar Capital LLC 1603 Orrington Ave. Evanston, Illinois 60201 (847) 905-4400 (Name, Addre

December 13, 2021 EX-99.1

JOINT FILING AGREEMENT

Exhibit 99.1 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k), as promulgated under the Securities Exchange Act of 1934, as amended, the persons named below agree to the joint filing on behalf of each of them a Statement on Schedule 13D (including amendments thereto) with regard to the common stock of Metromile Inc, and further agree that this Joint Filing Agreement be included as an Exhibi

November 22, 2021 425

The following updated FAQs, which were made available to employees of Metromile, Inc. (“Metromile” or the “Company”) on November 19, 2021, are being filed in connection with the acquisition of Metromile by Lemonade, Inc. (“Lemonade”).

Filed by Metromile, Inc. Pursuant to Rule 425 under the Securities Act of 1933, as amended and deemed filed pursuant to Rule 14a-12 under the Securities Exchange Act of 1934, as amended Subject Company: Metromile, Inc. (Commission File No. 001-39484) The following updated FAQs, which were made available to employees of Metromile, Inc. (?Metromile? or the ?Company?) on November 19, 2021, are being

November 19, 2021 424B3

Up to 50,828,643 Shares of Common Stock Up to 7,846,666 Shares of Common Stock Issuable Upon Exercise of Warrants Up to 180,000 Warrants

Filed Pursuant to Rule 424(b)(3) Registration No. 333-253055 PROSPECTUS SUPPLEMENT NO. 1 (To the Prospectus dated September 1, 2021) Up to 50,828,643 Shares of Common Stock Up to 7,846,666 Shares of Common Stock Issuable Upon Exercise of Warrants Up to 180,000 Warrants This prospectus supplement supplements the prospectus, dated September 1, 2021 (the ?Prospectus?), which forms a part of our regis

November 15, 2021 EX-99.1

Press Release of Metromile, Inc., dated November 15, 2021.

November 15, 2021 425

2

Filed by Metromile, Inc. Pursuant to Rule 425 under the Securities Act of 1933, as amended and deemed filed pursuant to Rule 14a-12 under the Securities Exchange Act of 1934, as amended Subject Company: Metromile, Inc. (Commission File No. 001-39484) FAQ update 11/10 Are there any contingencies to the deal? Is this deal pending approval of shareholders? There are some contingencies to the deal, in

November 15, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 15, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction of Incorporation) (Commission File

November 15, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 ☐ TRANSITION REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File No.

November 9, 2021 EX-10.1

Form of Voting and Support Agreement by and among Lemonade, Inc. and certain stockholders of the Company (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on November 9, 2021).

Exhibit 10.1 VOTING AND SUPPORT AGREEMENT THIS VOTING AND SUPPORT AGREEMENT (this ?Agreement?) is made and entered into as of [?], by and among Lemonade, Inc., a Delaware corporation (?Parent?); and [ ? ] (?Stockholder?). WHEREAS, contemporaneously with the execution of this Agreement, Parent, Citrus Merger Sub A, Inc., a Delaware corporation and a direct wholly owned subsidiary of Parent (?Acquis

November 9, 2021 EX-2.1

Agreement and Plan of Merger, dated November 8, 2021, by and among Lemonade, Inc., Citrus Merger Sub A, Inc., Citrus Merger Sub B, LLC and the Company (incorporated by reference to Exhibit 2.1 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on November 9, 2021).

Exhibit 2.1 EXECUTION VERSION AGREEMENT AND PLAN OF MERGER by and among LEMONADE, INC., a Delaware corporation; CITRUS MERGER SUB A, INC., a Delaware corporation; CITRUS MERGER SUB B, LLC, a Delaware limited liability company; and METROMILE, INC., a Delaware corporation Dated as of November 8, 2021 TABLE OF CONTENTS Page Section 1. THE MERGERS 2 1.1 The Mergers 2 1.2 Closing 2 1.3 Certificate of I

November 9, 2021 425

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 9, 2021 (November 8, 202

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 9, 2021 (November 8, 2021) METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File

November 9, 2021 EX-2.1

Agreement and Plan of Merger, dated November 8, 2021, by and among Lemonade, Inc., Citrus Merger Sub A, Inc., Citrus Merger Sub B, LLC and Metromile, Inc.

Exhibit 2.1 EXECUTION VERSION AGREEMENT AND PLAN OF MERGER by and among LEMONADE, INC., a Delaware corporation; CITRUS MERGER SUB A, INC., a Delaware corporation; CITRUS MERGER SUB B, LLC, a Delaware limited liability company; and METROMILE, INC., a Delaware corporation Dated as of November 8, 2021 TABLE OF CONTENTS Page Section 1. THE MERGERS 2 1.1 The Mergers 2 1.2 Closing 2 1.3 Certificate of I

November 9, 2021 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 9, 2021 (November 8, 2021) METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File

November 9, 2021 EX-10.1

Form of Voting and Support Agreement by and among Lemonade, Inc. and certain stockholders of Metromile, Inc.

Exhibit 10.1 VOTING AND SUPPORT AGREEMENT THIS VOTING AND SUPPORT AGREEMENT (this ?Agreement?) is made and entered into as of [?], by and among Lemonade, Inc., a Delaware corporation (?Parent?); and [ ? ] (?Stockholder?). WHEREAS, contemporaneously with the execution of this Agreement, Parent, Citrus Merger Sub A, Inc., a Delaware corporation and a direct wholly owned subsidiary of Parent (?Acquis

November 9, 2021 425

Metromile Customer Blog

425 1 ea150203-425metromileinc.htm FORM 425 Filed by Metromile, Inc. Pursuant to Rule 425 under the Securities Act of 1933, as amended and deemed filed pursuant to Rule 14a-12 under the Securities Exchange Act of 1934, as amended Subject Company: Metromile, Inc. (Commission File No. 001-39484) The following communications, which were made available on November 8, 2021, are being filed in connectio

November 8, 2021 EX-99.1

Lemonade To Acquire Metromile

Exhibit 99.1 Lemonade To Acquire Metromile New York (November 8,2021)?Lemonade (NYSE: LMND) the insurance company powered by Al and social good, and Metromile (NASDAQ: MILE, Ml LEW), the data science company focused on auto insurance, have entered into a definitive agreement pursuant to which Lemonade will acquire Metromile in an all-stock transaction that implies a fully diluted equity value of a

November 8, 2021 EX-99.1

Lemonade To Acquire Metromile

Exhibit 99.1 Lemonade To Acquire Metromile New York (November 8,2021)?Lemonade (NYSE: LMND) the insurance company powered by Al and social good, and Metromile (NASDAQ: MILE, Ml LEW), the data science company focused on auto insurance, have entered into a definitive agreement pursuant to which Lemonade will acquire Metromile in an all-stock transaction that implies a fully diluted equity value of a

November 8, 2021 425

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 8, 2021 METROMILE, INC.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 8, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File Number) (I.R.S. Emp

November 8, 2021 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 8, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File Number) (I.R.S. Emp

October 13, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 8, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File Number) (I.R.S. Empl

September 2, 2021 424B3

Up to 50,828,643 Shares of Common Stock Up to 7,846,666 Shares of Common Stock Issuable Upon Exercise of Warrants Up to 180,000 Warrants

PROSPECTUS Filed Pursuant to Rule 424(b)(3) Registration No. 333-253055 Up to 50,828,643 Shares of Common Stock Up to 7,846,666 Shares of Common Stock Issuable Upon Exercise of Warrants Up to 180,000 Warrants This prospectus relates to the issuance by us of an aggregate of up to 7,846,666 shares of our common stock, $0.0001 par value per share (?Common Stock?), which consists of (i) up to 180,000

August 27, 2021 POS AM

As filed with the Securities and Exchange Commission on August 27, 2021

As filed with the Securities and Exchange Commission on August 27, 2021 Registration No.

August 12, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 7, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File Number) (I.R.S. Emplo

August 10, 2021 EX-10.1

Offer Letter, dated April 17, 2021, by and between Metromile, Inc. and Regi Vengalil.

Exhibit 10.1 April 16, 2021 Regi Vengalil I am pleased to offer you a full-time position with Metromile, Inc. (the ?Company? as its Chief Financial Officer commencing on or before May 24, 2021. Duties and Responsibilities. You will report to the CEO of the Company. You shall have such job duties and responsibilities commensurate with and customary for your position, which duties may change from ti

August 10, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2021 ☐ TRANSITION REPORT PURS

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File No.

August 9, 2021 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 9, 2021 METROMILE, INC. (E

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 9, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File Number) (I.R.S. Emplo

August 9, 2021 EX-99.1

2

Exhibit 99.1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25

August 9, 2021 POS AM

As filed with the Securities and Exchange Commission on August 6, 2021

As filed with the Securities and Exchange Commission on August 6, 2021 Registration No.

August 3, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 28, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File Number) (I.R.S. Employ

June 3, 2021 S-8

As filed with the Securities and Exchange Commission on June 2, 2021

As filed with the Securities and Exchange Commission on June 2, 2021 Registration No.

June 3, 2021 EX-99.2

Forms of Option Agreement, Stock Option Grant Notice, Award Agreement and Restricted Stock Unit Award Grant Notice under the Metromile, Inc. 2021 Equity Incentive Plan.

Exhibit 99.2 Metromile, Inc. Stock Option Grant Notice (2021 Equity Incentive Plan) Metromile, Inc. (the ?Company?), pursuant to the Company?s 2021 Equity Incentive Plan (the ?Plan?), has granted to you (?Optionholder?) an option to purchase the number of shares of the Common Stock set forth below (the ?Option?). Your Option is subject to all of the terms and conditions as set forth herein and in

June 2, 2021 10-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 ☐ TRANSITION REPO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39484 METRO

June 2, 2021 EX-99.3

SUMMARY UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION

Exhibit 99.3 SUMMARY UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION The following summary unaudited pro forma condensed combined financial information has been derived from the unaudited pro forma condensed combined balance sheet as of December 31, 2020 and the unaudited pro forma condensed combined statement of operations for the year ended December 31, 2020, included in ?Unaudited

June 2, 2021 8-K/A

Financial Statements and Exhibits

united states SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A (Amendment No. 3) CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 9, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File

May 19, 2021 EX-99.1

2

Exhibit 99.1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21

May 19, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

united states SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 17, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File Number) (I.R.S. Employe

May 19, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2021 ☐ TRANSITION REPORT PUR

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File No.

May 18, 2021 8-K

Non-Reliance on Previously Issued Financial Statements or a Related Audit Report or Completed Interim Review, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 16, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File Number) (I.R.S. Employe

May 18, 2021 NT 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 12b-25 NOTIFICATION OF LATE FILING

NT 10-Q 1 ea141310-nt10qmetromile.htm NOTIFICATION OF LATE FILING UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 12b-25 NOTIFICATION OF LATE FILING Commission File Number 001-39484 (Check One): ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K ☒ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended: March 31, 2021 ☐ Transition Report on Form 10-K ☐ Transition Report on For

April 22, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

united states SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 22, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File Number) (I.R.S. Emplo

April 2, 2021 424B3

Up to 50,828,643 Shares of Common Stock Up to 7,846,666 Shares of Common Stock Issuable Upon Exercise of Warrants Up to 180,000 Warrants

PROSPECTUS Filed Pursuant to Rule 424(b)(3) Registration No. 333-253055 Up to 50,828,643 Shares of Common Stock Up to 7,846,666 Shares of Common Stock Issuable Upon Exercise of Warrants Up to 180,000 Warrants This prospectus relates to the issuance by us of an aggregate of up to 7,846,666 shares of our common stock, $0.0001 par value per share (?Common Stock?), which consists of (i) up to 180,000

March 31, 2021 EX-16.1

Letter from Grant Thornton LLP to the Securities and Exchange Commission, dated March 31, 2021.

Exhibit 16.1 March 31, 2021 U.S. Securities and Exchange Commission Office of the Chief Accountant 100 F Street, NE Washington, DC 20549 Re: Metromile, Inc. File No. 001-39484 Dear Sir or Madam: We have read Item 4.01 of Form 8-K of Metromile, Inc. dated March 31, 2021, and agree with the statements concerning our Firm contained therein. Very truly yours, /s/ GRANT THORNTON LLP

March 31, 2021 S-1/A

- REGISTRATION STATEMENT

As filed with the Securities and Exchange Commission on March 31, 2021 Registration No.

March 31, 2021 8-K/A

Financial Statements and Exhibits

united states SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A (Amendment No. 2) CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 9, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File

March 31, 2021 EX-99.1

METROMILE OPERATING COMPANY Index to Consolidated Financial Statements

Exhibit 99.1 METROMILE OPERATING COMPANY Index to Consolidated Financial Statements Page Report of Independent Registered Public Accounting Firm F-2 Consolidated Balance Sheets F-3 Consolidated Statements of Operations F-4 Consolidated Statements of Comprehensive Loss F-5 Consolidated Statements of Convertible Preferred Stock and Stockholders’ Deficit F-6 Consolidated Statements of Cash Flows F-7

March 31, 2021 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

united states SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 30, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File Number) (I.R.S. Emplo

March 31, 2021 EX-99.2

MANAGEMENT’S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS OF OPERATIONS

Exhibit 99.2 MANAGEMENT?S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS OF OPERATIONS The following discussion and analysis provides information that our management believes is relevant to an assessment and understanding of our results of operations and financial condition. This discussion and analysis should be read together with the consolidated financial statements and related note

March 31, 2021 10-K

Annual Report - ANNUAL REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39484 METROMILE, INC. (Exact na

March 31, 2021 EX-99.2

METROMILE, INC. 4Q20 EARNINGS CALL TRANSCRIPT | MARCH 30, 2021

Exhibit 99.2 METROMILE, INC. 4Q20 EARNINGS CALL TRANSCRIPT | MARCH 30, 2021 Garrett Edson: Thank you, Operator. Good afternoon, and welcome to Metromile?s fourth quarter and full-year 2020 earnings call. This afternoon, the Company released its financial results for the quarter and full-year ended December 31, 2020. The shareholder letter is available in the Investor Relations section of the Compa

March 31, 2021 EX-4.3

Description of Securities.

Exhibit 4.3 DESCRIPTION OF SECURITIES Metromile, Inc. (?we,? ?our,? ?us,? or the ?Company?) has two classes of securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the ?Exchange Act?): common stock, par value $0.0001 par value per share (the ?Common Stock?), and public warrants, each whole public warrant exercisable for one share of Common Stock at an exercise

March 31, 2021 EX-10.24

Offer Letter, dated February 11, 2021, by and between Metromile, Inc. and Dan Preston.

EX-10.24 3 f10k2020ex10-24metromile.htm OFFER LETTER, DATED FEBRUARY 11, 2021, BY AND BETWEEN METROMILE, INC. AND DAN PRESTON Exhibit 10.24 METROMILE, INC. February 11, 2021 Dan Preston via email: [email protected] Re: Employment Terms Dear Dan: On behalf of Metromile, Inc. (the “Company”), I am pleased to offer you continued employment at the Company on the terms set forth in this offer letter ag

March 31, 2021 CORRESP

-

Metromile, Inc. 425 Market Street #700 San Francisco, CA 94105 March 31, 2021 Securities and Exchange Commission Office of Finance Division of Corporation Finance 100 F. Street N.E. Washington, D.C. 20549-3010 Attention: Eric Envall, Staff Attorney RE: Metromile, Inc. Registration Statement on Form S-1 File No. 333-255055 Ladies and Gentlemen: Metromile, Inc. (the ?Registrant?) hereby requests tha

March 31, 2021 EX-99.3

SUMMARY UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION

Exhibit 99.3 SUMMARY UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION The following summary unaudited pro forma condensed combined financial information has been derived from the unaudited pro forma condensed combined balance sheet as of December 31, 2020 and the unaudited pro forma condensed combined statement of operations for the year ended December 31, 2020, included in ?Unaudited

March 31, 2021 8-K

Financial Statements and Exhibits, Changes in Registrant's Certifying Accountant

united states SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 31, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File Number) (I.R.S. Emplo

March 31, 2021 EX-99.1

Shareholder Letter Q4 2020 ( 7 . 7%) 2 0 18 2 0 19 2 0 20 (0.6%) A c c ide n t Y e ar C o n tri b u t ion Ma rgin 18.1% C o n tri b u t ion Ma rgin 2018 2019 2020 (1 0 . 4 %) 1 .5 % 11.8% Full Year 2020 Key Performance Indicators: 2 0 18 8 1 , 504 E

Exhibit 99.1 Shareholder Letter Q4 2020 ( 7 . 7%) 2 0 18 2 0 19 2 0 20 (0.6%) A c c ide n t Y e ar C o n tri b u t ion Ma rgin 18.1% C o n tri b u t ion Ma rgin 2018 2019 2020 (1 0 . 4 %) 1 .5 % 11.8% Full Year 2020 Key Performance Indicators: 2 0 18 8 1 , 504 E ndin g P oli c i e s in F o r ce ( PIF) 92,635 88,099 2 0 19 2 0 20 A c c ide n t Y e ar L o s s R a t io 2 0 18 8 0 . 6 % 7 5 . 7 % 5 7

February 24, 2021 SC 13D

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. __ )* Metromile, Inc. (Name of Issuer) Common Stock, $.0001 par value (Title of Class of Securities) (CUSIP

Schedule 13D UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. )* Metromile, Inc. (Name of Issuer) Common Stock, $.0001 par value (Title of Class of Securities) 0001819035 (CUSIP Number) Louis S. Citron, Esq. New Enterprise Associates 1954 Greenspring Drive, Suite 600, Timonium, MD 21093 (410) 842-4000 (Nam

February 19, 2021 EX-99.1

JOINT FILING AGREEMENT

Exhibit 99.1 JOINT FILING AGREEMENT The undersigned hereby agree that the Statement on Schedule 13D, dated February 19, 2021, with respect to the Common Shares of Metromile, Inc. is filed on behalf of each of us pursuant to and in accordance with the provisions of Rule 13d-1(k) under the Securities Exchange Act of 1934, as amended. Each of the undersigned agrees to be responsible for the timely fi

February 19, 2021 SC 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )* Metromile, Inc. (Name of Issuer) Common Stock, $0.0001 par value per share (Title of Class of Securities)

SC 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )* Metromile, Inc. (Name of Issuer) Common Stock, $0.0001 par value per share (Title of Class of Securities) 591697115 (CUSIP Number) February 9, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the r

February 19, 2021 EX-99.1

JOINT FILING AGREEMENT

EX-99.1 Exhibit 99.1 JOINT FILING AGREEMENT The undersigned agree that this Schedule 13G dated February 19, 2021 relating to the common stock, par value $0.0001 per share, of Metromile, Inc. shall be filed on behalf of the undersigned. INTACT FINANCIAL CORPORATION By: /s/ Frédéric Cotnoir Name: Frédéric Cotnoir Title: Senior Vice President, Corporate and Legal Services, and Secretary INTACT VENTUR

February 19, 2021 SC 13D

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 Metromile, Inc. (Name of Issuer) Common Stock, par value $0.0001 per share (Title of Class of Securities) (CUSIP Number) Aj

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 Metromile, Inc. (Name of Issuer) Common Stock, par value $0.0001 per share (Title of Class of Securities) 591697107 (CUSIP Number) Ajay Mehra Chief Legal Officer Hudson Structured Capital Management Ltd. 2187 Atlantic Street – 4th Floor Stamford, Connecticut 06902 Telephon

February 19, 2021 SC 13G

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Metromile, Inc. (Name of Issuer) Common stock, par value $0.0001 per share (Title of Class of Securities) (CUSIP Number

SC 13G SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Metromile, Inc. (Name of Issuer) Common stock, par value $0.0001 per share (Title of Class of Securities) 591697107 (CUSIP Number) February 9, 2021 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant t

February 19, 2021 EX-99.1

JOINT FILING AGREEMENT

EX-99.1 EXHIBIT 99.1 JOINT FILING AGREEMENT Each of the undersigned, pursuant to Rule 13d-1(k)(1) under the Act, hereby agrees and acknowledges that only one statement containing the information required by Schedule 13G need be filed with respect to the ownership by each of the undersigned of the Common Stock and the information required by this Schedule 13G, to which this Agreement is attached as

February 16, 2021 SC 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* METROMILE, INC. (Name of Issuer) Common Stock, $0.001 par value (Title of Class of Securities) (CUSIP Num

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* METROMILE, INC. (Name of Issuer) Common Stock, $0.001 par value (Title of Class of Securities) 591697107 (CUSIP Number) December 31, 2020 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to w

February 16, 2021 SC 13G/A

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G (RULE 13d - 102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO 13d-1(b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO 13d-2(b) (Amendment No. 1)* Metromile, I

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G (RULE 13d - 102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO 13d-1(b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO 13d-2(b) (Amendment No. 1)* Metromile, Inc. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 591697107 (CUSIP Number) December 31, 2020 (Date

February 12, 2021 EX-21.1

List of Subsidiaries.

Exhibit 21.1 Legal Name Jurisdiction of Organization Metromile Operating Company Delaware Metromile Insurance Company Delaware Metromile Insurance Services, LLC California Metromile Enterprise Solutions, LLC California

February 12, 2021 EX-16.1

Letter from Grant Thornton LLP to the SEC, dated February 12, 2021.

Exhibit 16.1 February 11, 2021 U.S. Securities and Exchange Commission Office of the Chief Accountant 100 F Street, NE Washington, DC 20549 Re: Metromile, Inc. File No. 001-39484 Dear Sir or Madam: We have read Item 4.01 of Form 8-K of Metromile, Inc. dated February 11, 2021, and agree with the statements concerning our Firm contained therein. Very truly yours, /s/ GRANT THORNTON LLP

February 12, 2021 EX-4.2

Form of Warrant Certificate of Metromile, Inc.

Exhibit 4.2 [Form of Warrant Certificate] [FACE] Number Warrants THIS WARRANT SHALL BE VOID IF NOT EXERCISED PRIOR TO THE EXPIRATION OF THE EXERCISE PERIOD PROVIDED FOR IN THE WARRANT AGREEMENT DESCRIBED BELOW METROMILE, INC. A Delaware corporation CUSIP 591697115 Warrant Certificate This Warrant Certificate certifies that , or registered assigns, is the registered holder of warrant(s) (the ?Warra

February 12, 2021 S-1

Power of Attorney (included on signature page of initial filing)

As filed with the Securities and Exchange Commission on February 12, 2021 Registration No.

February 12, 2021 EX-4.1

Form of Common Stock Certificate of the Company.

Exhibit 4.1 NUMBER SHARES SEE REVERSE FOR CERTAIN DEFINITIONS CUSIP 591697115 METROMILE, INC. A DELAWARE CORPORATION COMMON STOCK This Certifies that is the owner of FULLY PAID AND NON-ASSESSABLE SHARES OF COMMON STOCK, $0.0001 PAR VALUE PER SHARE EACH, OF METROMILE, INC. (THE ?CORPORATION?) transferable on the books of the Corporation in person or by duly authorized attorney upon surrender of thi

February 11, 2021 8-K/A

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Amendment to Registrant's Code of Ethics, or Waiver of a Provision of the Code of Ethics, Material Modification to Rights of Security Holders, Financial Statements and Exhibits - AMENDMENT NO. 1 TO FORM 8-K

united states SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A (Amendment No.1) CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 9, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File

February 11, 2021 EX-2.3

Amendment No. 2 to the Agreement and Plan of Merger and Reorganization, dated November 24, 2020, and as amended on January 12, 2021 and further amended on February 8, 2021, by and among INSU Acquisition Corp. II, INSU II Merger Sub Corp., and MetroMile, Inc. (incorporated by reference to Exhibit 2.3 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on February 11, 2021).

Exhibit 2.3 SECOND AMENDMENT TO AGREEMENT AND PLAN OF MERGER AND REORGANIZATION This SECOND AMENDMENT (this “Second Amendment”) to the Agreement and Plan of Merger and Reorganization, dated as of November 24, 2020, as amended on January 12, 2021 (the “Merger Agreement”), by and among INSU Acquisition Corp. II, a Delaware corporation (“Parent”), INSU II Merger Sub Corp., a Delaware corporation and

February 11, 2021 EX-3.2

Second Amended and Restated Bylaws of the Company, dated February 9, 2021 (incorporated by reference to Exhibit 3.2 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on February 11, 2021).

Exhibit 3.2 AMENDED AND RESTATED BYLAWS OF METROMILE, INC. (A DELAWARE CORPORATION) ARTICLE I OFFICES Section 1. Registered Office. The registered office of the corporation in the State of Delaware shall be as set forth in the Certificate of Incorporation. Section 2. Other Offices. The corporation shall also have and maintain an office or principal place of business at such place as may be fixed b

February 11, 2021 EX-16.1

Letter from Grant Thornton LLP to the Securities and Exchange Commission, dated February 11, 2021 (incorporated by reference to Exhibit 16.1 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on February 11, 2021).

Exhibit 16.1 February 11, 2021 U.S. Securities and Exchange Commission Office of the Chief Accountant 100 F Street, NE Washington, DC 20549 Re: Metromile, Inc. File No. 001-39484 Dear Sir or Madam: We have read Item 4.01 of Form 8-K of Metromile, Inc. dated February 10, 2021, and agree with the statements concerning our Firm contained therein. Very truly yours, /s/ GRANT THORNTON LLP

February 11, 2021 EX-10.5

Omnibus Amendment No. 2 to Note Purchase and Security Agreement, by and between Metromile, Inc., HSCM Bermuda Fund Ltd., and the Schedule of Holders listed on Exhibit B, dated February 9, 2021 (incorporated by reference to Exhibit 10.5 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on February 11, 2021).

Exhibit 10.5 METROMILE, INC. OMNIBUS AMENDMENT NO. 2 TO THE NOTE PURCHASE AND SECURITY AGREEMENT February 9, 2021 This OMNIBUS AMENDMENT NO. 2 (this “Amendment”) to the Note Purchase and Security Agreement, dated as of April 14, 2020, by and among Metromile, Inc. (the “Company”), INSU Acquisition Corp. II, a Delaware corporation (the “Parent”), the other undersigned Guarantors, the Holders, and th

February 11, 2021 EX-10.1

Form of Indemnification Agreement by and between the Company and its directors and officers (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on February 11, 2021).

Exhibit 10.1 METROMILE, Inc. INDEMNIFICATION AGREEMENT This Indemnification Agreement (this “Agreement”) is dated as of , 20 and is between Metromile, Inc., a Delaware corporation (the “Company”), and (“Indemnitee”). Recitals A. Indemnitee’s service to the Company substantially benefits the Company. B. Individuals are reluctant to serve as directors or officers of corporations or in certain other

February 11, 2021 EX-10.7

Offer Letter, dated February 11, 2021, by and between Metromile, Inc. and Dan Preston (incorporated by reference to Exhibit 10.24 to the Company’s Annual Report on Form 10-K, filed with the Securities and Exchange Commission on March 31, 2021).

Exhibit 10.7 Metromile, Inc. February 11, 2021 Dan Preston via email: [email protected] Re: Employment Terms Dear Dan: On behalf of Metromile, Inc. (the “Company”), I am pleased to offer you continued employment at the Company on the terms set forth in this offer letter agreement (the “Agreement”). This Agreement shall become effective on the date that it is signed by you (the “Effective Date”) an

February 11, 2021 EX-99.1

Unaudited pro forma condensed combined financial information of INSU Acquisition Corp. II and MetroMile, Inc. as of September 30, 2020 and for the year ended December 31, 2019 and the nine months ended September 30, 2020.

Exhibit 99.1 Unaudited pro forma condensed combined financial information of INSU Acquisition Corp. II and MetroMile, Inc. as of September 30, 2020 and for the year ended December 31, 2019 and the nine months ended September 30, 2020. Introduction INSU Acquisition Corp. II (“INSU”) is providing the following unaudited pro forma condensed combined financial information to aid you in your analysis o

February 11, 2021 EX-3.1

Second Amended and Restated Certificate of Incorporation of the Company, dated February 9, 2021 (incorporated by reference to Exhibit 3.1 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on February 11, 2021).

Exhibit 3.1 SECOND AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF INSU Acquisition Corp. II INSU Acquisition Corp. II, a corporation organized and existing under the laws of the State of Delaware, hereby certifies that: ONE: The name of this corporation is “INSU Acquisition Corp. II”. The original certificate of incorporation under the name of “HC Merger Corp.” was filed with the Secretary o

February 11, 2021 EX-4.1

Amended and Restated Registration Rights Agreement, dated February 9, 2021, by and among the Company and certain security holders of the Company (incorporated by reference to Exhibit 4.1 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on February 11, 2021).

Exhibit 4.1 AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT THIS AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT (this “Agreement”), dated as of February 9, 2021, is made and entered into by and among each of INSU Acquisition Corp. II, a Delaware corporation (the “Company”), Insurance Acquisition Sponsor II, LLC, a Delaware limited liability company, Dioptra Advisors II, LLC, a Delaware limi

February 11, 2021 EX-10.2

Form of Subscription Agreement, dated as of November 24, 2020, by and between INSU Acquisition Corp. II and the undersigned subscriber party thereto.

Exhibit 10.2 SUBSCRIPTION AGREEMENT This SUBSCRIPTION AGREEMENT (this “Subscription Agreement”) is entered into on November , 2020, by and among INSU Acquisition Corp. II, a Delaware corporation (the “Issuer”), and the subscriber party set forth on the signature page hereto (“Subscriber”). WHEREAS, the Issuer is concurrently with the execution and delivery hereof entering into an Agreement and Pla

February 11, 2021 8-K

Changes in Control of Registrant, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Change in Shell Company Status, Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Changes in Registrant's Certifying Accountant, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Completion of Acquisition or Disposition of Assets

united states SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 9, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or Other Jurisdiction (Commission File Number) (I.R.S. Emp

February 10, 2021 SC 13G

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Metromile, Inc. (Name of Issuer) Common Stock, par value $0.0001 per share (Title of Class of Securities) (CUSIP Number

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Metromile, Inc. (Name of Issuer) Common Stock, par value $0.0001 per share (Title of Class of Securities) 591697 107 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to whi

February 9, 2021 8-K

Submission of Matters to a Vote of Security Holders - CURRENT REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 9, 2021 METROMILE, INC. (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation or organiza

February 4, 2021 SC 13G/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (AMENDMENT NO. 1) INSU ACQUISITION CORP. II (Name of Issuer) CLASS A COMMON STOCK, PAR VALUE $0.0001 PER SHARE (Title of Cl

SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (AMENDMENT NO. 1) INSU ACQUISITION CORP. II (Name of Issuer) CLASS A COMMON STOCK, PAR VALUE $0.0001 PER SHARE (Title of Class of Securities) 457821106 (CUSIP Number) DECEMBER 31, 2020 (Date of event which requires filing of this statement) Check the appropria

February 4, 2021 SC 13G

SCHEDULE 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* INSU Acquisition Corp. II (Name of Issuer) Common Stock (Title of Class of Securities) 457821106 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant to which thi

February 1, 2021 EX-99.2

Welcoming Ryan Graves to the Metromile Community

Exhibit 99.2 Welcoming Ryan Graves to the Metromile Community We started Metromile to create digital insurance for an increasingly digital world. We believe that auto insurance doesn’t work for many people: It overcharges 65% of drivers unfairly and isn’t customer-centric or adaptive to how people actually get around. Ryan Graves, a member of Uber’s founding team, will be joining Metromile’s board

February 1, 2021 EX-99.1

Uber Veteran Ryan Graves to Invest $50 Million in Metromile, Will Join Board of Directors Graves’ investment joins Chamath Palihapitiya’s Social Capital, Mark Cuban and leading institutional investors

Exhibit 99.1 Uber Veteran Ryan Graves to Invest $50 Million in Metromile, Will Join Board of Directors Graves’ investment joins Chamath Palihapitiya’s Social Capital, Mark Cuban and leading institutional investors SAN FRANCISCO — February 1, 2021 — Metromile, Inc., a leading digital insurance platform and pay-per-mile auto insurer, today announced Ryan Graves, Uber’s former senior vice president o

February 1, 2021 EX-99.1

Uber Veteran Ryan Graves to Invest $50 Million in Metromile, Will Join Board of Directors Graves’ investment joins Chamath Palihapitiya’s Social Capital, Mark Cuban and leading institutional investors

Exhibit 99.1 Uber Veteran Ryan Graves to Invest $50 Million in Metromile, Will Join Board of Directors Graves’ investment joins Chamath Palihapitiya’s Social Capital, Mark Cuban and leading institutional investors SAN FRANCISCO — February 1, 2021 — Metromile, Inc., a leading digital insurance platform and pay-per-mile auto insurer, today announced Ryan Graves, Uber’s former senior vice president o

February 1, 2021 8-K

Other Events - CURRENT REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 1, 2021 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation o

February 1, 2021 425

Merger Prospectus - CURRENT REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 1, 2021 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation o

February 1, 2021 8-K

Regulation FD Disclosure, Financial Statements and Exhibits - CURRENT REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 1, 2021 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation o

February 1, 2021 EX-99.2

Welcoming Ryan Graves to the Metromile Community

Exhibit 99.2 Welcoming Ryan Graves to the Metromile Community We started Metromile to create digital insurance for an increasingly digital world. We believe that auto insurance doesn’t work for many people: It overcharges 65% of drivers unfairly and isn’t customer-centric or adaptive to how people actually get around. Ryan Graves, a member of Uber’s founding team, will be joining Metromile’s board

February 1, 2021 425

Merger Prospectus - CURRENT REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 1, 2021 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation o

January 29, 2021 SC 13G/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* INSU Acquisition Corp. II (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of C

SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* INSU Acquisition Corp. II (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 457821304 (CUSIP Number) December 31, 2020 (Date of Event which Requires Filing of this Statement) Check the appropriate

January 29, 2021 425

Merger Prospectus - FORM 425

Filed by Insurance Acquisition Corp. II pursuant to Rule 425 under the Securities Act of 1933, as amended, and deemed filed pursuant to Rule 14a-12 under the Securities Exchange Act of 1934, as amended Subject Company: Insurance Acquisition Corp. II Commission File No.: 001-39484 Metromile Receives the Necessary Regulatory Approvals for Proposed Business Combination with INSU Acquisition Corp. II

January 21, 2021 EX-99.1

All materials are confidential and property of 1 Dis c lai m er All materials are confidential and property of 2 This presentation is provided for informational purposes only and has been prepared to assist interested parties in making their own evalua

Exhibit 99.1 All materials are confidential and property of 1 Dis c lai m er All materials are confidential and property of 2 This presentation is provided for informational purposes only and has been prepared to assist interested parties in making their own evaluation with respect to a potential business combination (the “proposed business combination”) between MetroMile, Inc. (“Metromile”) and INS

January 21, 2021 EX-99.1

All materials are confidential and property of 1 Dis c lai m er All materials are confidential and property of 2 This presentation is provided for informational purposes only and has been prepared to assist interested parties in making their own evalua

Exhibit 99.1 All materials are confidential and property of 1 Dis c lai m er All materials are confidential and property of 2 This presentation is provided for informational purposes only and has been prepared to assist interested parties in making their own evaluation with respect to a potential business combination (the “proposed business combination”) between MetroMile, Inc. (“Metromile”) and INS

January 21, 2021 425

Merger Prospectus - CURRENT REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 21, 2021 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation o

January 21, 2021 8-K

Regulation FD Disclosure, Financial Statements and Exhibits - CURRENT REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 21, 2021 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation o

January 15, 2021 425

Merger Prospectus - 425

Filed by Insurance Acquisition Corp. II pursuant to Rule 425 under the Securities Act of 1933, as amended, and deemed filed pursuant to Rule 14a-12 under the Securities Exchange Act of 1934, as amended Subject Company: Insurance Acquisition Corp. II Commission File No.: 001-39484 INSU Acquisition Corp. II Announces Effectiveness of Registration Statement for Proposed Business Combination with Metr

January 15, 2021 424B3

INSU ACQUISITION CORP. II 2929 Arch Street, Suite 1703 Philadelphia, Pennsylvania 19104 PROXY STATEMENT/PROSPECTUS FOR SPECIAL MEETING IN LIEU OF 2021 ANNUAL MEETING OF STOCKHOLDERS AND PROSPECTUS FOR 97,212,500 SHARES OF COMMON STOCK OF INSU ACQUISI

Filed Pursuant to Rule 424(b)(3) Registration Statement No. 333-250989 INSU ACQUISITION CORP. II 2929 Arch Street, Suite 1703 Philadelphia, Pennsylvania 19104 PROXY STATEMENT/PROSPECTUS FOR SPECIAL MEETING IN LIEU OF 2021 ANNUAL MEETING OF STOCKHOLDERS AND PROSPECTUS FOR 97,212,500 SHARES OF COMMON STOCK OF INSU ACQUISITION CORP. II. Dear INSU Acquisition Corp. II Stockholders: On November 24, 202

January 14, 2021 S-4/A

Amendment No. 1 to the Agreement and Plan of Merger and Reorganization dated November 24, 2020, dated January 12, 2021 by and among INSU Acquisition Corp. II, INSU II Merger Sub Corp., and MetroMile, Inc. (incorporated by reference to Annex AA to the Company’s Proxy Statement/Prospectus included in the Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on January 14, 2021).

As filed with the Securities and Exchange Commission on January 14, 2021 Registration No.

January 14, 2021 CORRESP

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INSU ACQUISITION CORP. II 2929 Arch Street, Suite 1703 Philadelphia, PA 19104 January 14, 2021 VIA EDGAR TRANSMISSION Securities and Exchange Commission Office of Finance Division of Corporation Finance 100 F. Street NE Washington, D.C. 20549-3010 Re: Registration Statement on Form S-4 File No. 333-250989 Gentlemen/Ladies: INSU Acquisition Corp. II (the ?Company?) hereby requests acceleration of t

January 14, 2021 EX-99.3

Form of Proxy Card.*

Exhibit 99.3 PRELIMINARY PROXY CARD - SUBJECT TO COMPLETION PROXY CARD INSU ACQUISITION CORP. II 2929 Arch Street, Suite 1703 Philadelphia, PA 19104-2870 (215) 701-9555 YOUR VOTE IS IMPORTANT THIS PROXY IS SOLICITED BY THE BOARD OF DIRECTORS FOR THE SPECIAL MEETING OF STOCKHOLDERS OF INSU ACQUISITION CORP. II TO BE HELD ON FEBRUARY 9, 2021 The undersigned, revoking any previous proxies, hereby ack

January 13, 2021 425

Merger Prospectus - CURRENT REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 12, 2021 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation o

January 13, 2021 EX-10.19

Offer Letter, dated January 30, 2013, by and between MetroMile, Inc. and Dan Preston (incorporated by reference to Exhibit 10.19 to the Company’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on January 13, 2021).

EX-10.19 3 fs42020a2ex10-19insuacq2.htm OFFER LETTER, DATED JANUARY 30, 2013 BY AND BETWEEN METROMILE, INC. AND DAN PRESTON Exhibit 10.19 MetroMile, Inc. January 30, 2013 Daniel Preston [] Dear Daniel: I am pleased to offer you a position with MetroMile, Inc. (the “Company”) as Chief Technology Officer. If you decide to join us, you will receive an annual salary of $150,000, which will be paid sem

January 13, 2021 S-4/A

- AMENDMENT NO. 2 TO FORM S-4

As filed with the Securities and Exchange Commission on January 12, 2021 Registration No.

January 13, 2021 EX-10.23

Offer Letter, dated January 3, 2020, by and between MetroMile, Inc. and Jesse McKendry (incorporated by reference to Exhibit 10.23 to the Company’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on January 13, 2021).

EX-10.23 7 fs42020a2ex10-23insuacq2.htm OFFER LETTER, DATED JANUARY 3, 2020 BY AND BETWEEN METROMILE, INC. AND JESSE MCKENDRY Exhibit 10.23 1/3/2020 Jesse McKendry, I am pleased to offer you a full-time position with Metromile, Inc. (the “Company”) in Cleveland, as an Insurance Product Manager, commencing on or before January 13, 2020. Duties and Responsibilities. You will initially report to Jeff

January 13, 2021 EX-99.4

Consent of Colin Bryant to be named as director.*

Exhibit 99.4 January 12, 2021 INSU Acquisition Corp. II 2929 Arch Street, Suite 1703 Philadelphia, PA 19104-2870 Consent to Reference in Proxy Statement/Prospectus INSU Acquisition Corp. II (the “Company”) is filing a Registration Statement on Form S-4 with the Securities and Exchange Commission under the Securities Act of 1933, as amended (the “Securities Act”). In connection therewith, I hereby

January 13, 2021 EX-99.3

Form of Proxy Card.*

Exhibit 99.3 PRELIMINARY PROXY CARD - SUBJECT TO COMPLETION PROXY CARD INSU ACQUISITION CORP. II 2929 Arch Street, Suite 1703 Philadelphia, PA 19104-2870 (215) 701-9555 YOUR VOTE IS IMPORTANT THIS PROXY IS SOLICITED BY THE BOARD OF DIRECTORS FOR THE SPECIAL MEETING OF STOCKHOLDERS OF INSU ACQUISITION CORP. II TO BE HELD ON [-], 2021 The undersigned, revoking any previous proxies, hereby acknowledg

January 13, 2021 EX-99.1

Transcript of Interview with Dan Preston, CEO of Metromile, at the ICR Conference - January 12, 2021

Exhibit 99.1 Transcript of Interview with Dan Preston, CEO of Metromile, at the ICR Conference - January 12, 2021 Jimmy Bhullar: Hi, good morning everyone. My name is Jimmy Bhullar, I'm the insurance analyst at J.P. Morgan on the sell side. I'm going to be speaking with Dan Preston, Dan is the CEO of Metromile. As many of you might know, Metromile's a digital insurance company that's targeting the

January 13, 2021 EX-10.21

Offer Letter, dated September 21, 2017, by and between MetroMile, Inc. and Lindsay Alexovich (incorporated by reference to Exhibit 10.21 to the Company’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on January 13, 2021).

Exhibit 10.21 September 21, 2017 Lindsay Alexovich, I am pleased to offer you a full-time position with Metromile, Inc. (the "Company") in San Francisco (Headquarters), as a Vice President, Controller, commencing on or before October 30, 2017. Duties and Responsibilities. You will initially report to Carrie Dolan, CFO. You shall have such job duties and responsibilities commensurate with your posi

January 13, 2021 EX-99.7

Consent of Dan Preston to be named as director.*

Exhibit 99.7 January 12, 2021 INSU Acquisition Corp. II 2929 Arch Street, Suite 1703 Philadelphia, PA 19104-2870 Consent to Reference in Proxy Statement/Prospectus INSU Acquisition Corp. II (the “Company”) is filing a Registration Statement on Form S-4 with the Securities and Exchange Commission under the Securities Act of 1933, as amended (the “Securities Act”). In connection therewith, I hereby

January 13, 2021 EX-10.20

Offer Letter, dated January 18, 2019, by and between MetroMile, Inc. and Paw Andersen (incorporated by reference to Exhibit 10.20 to the Company’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on January 13, 2021).

EX-10.20 4 fs42020a2ex10-20insuacq2.htm OFFER LETTER, DATED JANUARY 18, 2019 BY AND BETWEEN METROMILE, INC. AND PAW ANDERSEN Exhibit 10.20 January 18, 2019 Paw Andersen, I am pleased to offer you a full-time position with Metromile, Inc. (the “Company”) in San Francisco, as a Chief Technology Officer, commencing on or before March 12, 2019. Duties and Responsibilities. You will initially report to

January 13, 2021 8-K

Regulation FD Disclosure, Financial Statements and Exhibits - CURRENT REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 12, 2021 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation o

January 13, 2021 EX-99.1

Transcript of Interview with Dan Preston, CEO of Metromile, at the ICR Conference - January 12, 2021

Exhibit 99.1 Transcript of Interview with Dan Preston, CEO of Metromile, at the ICR Conference - January 12, 2021 Jimmy Bhullar: Hi, good morning everyone. My name is Jimmy Bhullar, I'm the insurance analyst at J.P. Morgan on the sell side. I'm going to be speaking with Dan Preston, Dan is the CEO of Metromile. As many of you might know, Metromile's a digital insurance company that's targeting the

January 13, 2021 EX-10.22

Offer Letter, dated December 16, 2019, by and between MetroMile, Inc. and Mark Gundacker (incorporated by reference to Exhibit 10.22 to the Company’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on January 13, 2021).

Exhibit 10.22 December 16, 2019 Mark Gundacker, I am pleased to offer you a full-time position with Metromile, Inc. (the “Company”) in San Francisco, as a Chief People Officer, commencing on or before January 13, 2020. Duties and Responsibilities. You will initially report to Dan Preston, CEO. You shall have such job duties and responsibilities commensurate with your position, which duties may cha

January 13, 2021 EX-10.24

Form of MetroMile, Inc. Confidential Information and Invention Assignment Agreement (incorporated by reference to Exhibit 10.24 to the Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on January 13, 2021).

Exhibit 10.24 METROMILE, INC. CONFIDENTIAL INFORMATION AND INVENTION ASSIGNMENT AGREEMENT As a condition of my business relationship with MetroMile, Inc., its subsidiaries, affiliates, successors or assigns (together, the “Company”), and in consideration of my business relationship with the Company and my receipt of the compensation now and hereafter paid to me on behalf of Company, I agree to the

January 13, 2021 EX-10.26

At-Will Employment, Confidential Information, Invention Assignment and Arbitration Agreement, dated November 4, 2017, by and between MetroMile, Inc. and Lindsay Alexovich (incorporated by reference to Exhibit 10.26 to the Company’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on January 13, 2021).

Exhibit 10.26 METROMlLE, INC. AT-WILL EMPLOYMENT, CONFIDENTIAL INFORMATION, INVENTION ASSIGNMENT, AND ARBITRATION AGREEMENT As a condition of my employment with MetroMile, Inc., its subsidiaries, affiliates, successors or assigns (together, the “Company”), and in consideration of my employment with the Company and my receipt of the compensation now and hereafter paid to me by Company, I agree to t

January 13, 2021 EX-99.8

Consent of Vikas Singhal to be named as director.*

Exhibit 99.8 January 12, 2021 INSU Acquisition Corp. II 2929 Arch Street, Suite 1703 Philadelphia, PA 19104-2870 Consent to Reference in Proxy Statement/Prospectus INSU Acquisition Corp. II (the “Company”) is filing a Registration Statement on Form S-4 with the Securities and Exchange Commission under the Securities Act of 1933, as amended (the “Securities Act”). In connection therewith, I hereby

January 13, 2021 EX-10.25

At-Will Employment, Confidential Information, Invention Assignment and Arbitration Agreement, dated February 7, 2013, by and between MetroMile, Inc. and Dan Preston (incorporated by reference to Exhibit 10.25 to the Company’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on January 13, 2021).

EX-10.25 9 fs42020a2ex10-25insuacq2.htm AT-WILL EMPLOYMENT, CONFIDENTIAL INFORMATION, INVENTION ASSIGNMENT AND ARBITRATION AGREEMENT, DATED BY AND BETWEEN METROMILE, INC. AND DAN PRESTON, DATED FEBRUARY 7, 2013 Exhibit 10.25 METROMILE, INC. AT-WILL EMPLOYMENT, CONFIDENTIAL INFORMATION, INVENTION ASSIGNMENT, AND ARBITRATION AGREEMENT As a condition of my employment with MetroMile, Inc., its subsidi

January 13, 2021 EX-99.9

Consent of Ryan Graves to be named as director.*

Exhibit 99.9 January 12, 2021 INSU Acquisition Corp. II 2929 Arch Street, Suite 1703 Philadelphia, PA 19104-2870 Consent to Reference in Proxy Statement/Prospectus INSU Acquisition Corp. II (the “Company”) is filing a Registration Statement on Form S-4 with the Securities and Exchange Commission under the Securities Act of 1933, as amended (the “Securities Act”). In connection therewith, I hereby

January 13, 2021 EX-99.6

Consent of David Friedberg to be named as director.*

Exhibit 99.6 January 12, 2021 INSU Acquisition Corp. II 2929 Arch Street, Suite 1703 Philadelphia, PA 19104-2870 Consent to Reference in Proxy Statement/Prospectus INSU Acquisition Corp. II (the “Company”) is filing a Registration Statement on Form S-4 with the Securities and Exchange Commission under the Securities Act of 1933, as amended (the “Securities Act”). In connection therewith, I hereby

January 13, 2021 EX-99.5

Consent of Betsy Cohen to be named as director.*

Exhibit 99.5 January 12, 2021 INSU Acquisition Corp. II 2929 Arch Street, Suite 1703 Philadelphia, PA 19104-2870 Consent to Reference in Proxy Statement/Prospectus INSU Acquisition Corp. II (the “Company”) is filing a Registration Statement on Form S-4 with the Securities and Exchange Commission under the Securities Act of 1933, as amended (the “Securities Act”). In connection therewith, I hereby

January 12, 2021 CORRESP

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January 12, 2021 VIA EDGAR TRANSMISSION Jessica Livingston Office of Finance U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street NE Washington, D.C. 20549 Re: INSU ACQUISITION CORP. II Amendment No. 1 to Registration Statement on Form S-4 File No. 333-250989 Filed December 31, 2020 Dear Ms. Livingston: On behalf of INSU Acquisition Corp. II, a Delaware corporation

January 7, 2021 EX-99.1

Metromile to Participate at the ICR Conference 2021

Exhibit 99.1 Metromile to Participate at the ICR Conference 2021 SAN FRANCISCO – January 7, 2021 – Metromile, Inc. (“Metromile”), a leading digital insurance platform and pay-per-mile auto insurer, today announced that Chief Executive Officer Dan Preston will participate in a virtual fireside chat at the ICR Conference on Tuesday, January 12, 2021, at 9:30 am Eastern Time. A live webcast of the fi

January 7, 2021 8-K

Regulation FD Disclosure, Financial Statements and Exhibits - CURRENT REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 7, 2021 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation or

January 7, 2021 EX-99.1

Metromile to Participate at the ICR Conference 2021

Exhibit 99.1 Metromile to Participate at the ICR Conference 2021 SAN FRANCISCO – January 7, 2021 – Metromile, Inc. (“Metromile”), a leading digital insurance platform and pay-per-mile auto insurer, today announced that Chief Executive Officer Dan Preston will participate in a virtual fireside chat at the ICR Conference on Tuesday, January 12, 2021, at 9:30 am Eastern Time. A live webcast of the fi

January 7, 2021 425

Merger Prospectus - CURRENT REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 7, 2021 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation or

December 31, 2020 EX-10.15

Office Lease by and between 425 MKT REIT, LLC and Metromile, Inc., dated May 16, 2019 (incorporated by reference to Exhibit 10.15 to the Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on January 14, 2021).

Exhibit 10.15 OFFICE LEASE 425 MKT REIT, LLC (LANDLORD) AND METROMILE, INC. (TENANT) 425 MARKET STREET San Francisco, California Table of Contents Page Article One BASIC LEASE PROVISIONS 1 1.01 BASIC LEASE PROVISIONS 1 1.02 ENUMERATION OF EXHIBITS & RIDER(S) 3 1.03 DEFINITIONS 3 Article Two PREMISES, TERM AND FAILURE TO GIVE POSSESSION 9 2.01 LEASE OF PREMISES 9 2.02 TERM 9 2.03 FAILURE TO GIVE PO

December 31, 2020 EX-10.16

Note Purchase and Security Agreement, by and between Metromile, Inc., HSCM Bermuda Fund Ltd., and the Schedule of Holders listed on Exhibit B, dated April 14, 2020.†

Exhibit 10.16 Execution Version NOTE PURCHASE AND SECURITY AGREEMENT This Note Purchase and Security Agreement, dated as of April 14, 2020 (this “Agreement”), is entered into by and among Metromile, Inc., a Delaware corporation (the “Company”), the undersigned Guarantors, the persons listed on the Schedule of Holders attached hereto as Exhibit B (collectively, the “Holders”, and each, a “Holder”)

December 31, 2020 CORRESP

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December 31, 2020 VIA EDGAR TRANSMISSION Jessica Livingston Office of Finance U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street NE Washington, D.C. 20549 Re: INSU ACQUISITION CORP II Registration Statement on Form S-4 File No. 333-250989 Filed November 27, 2020 Dear Ms. Livingston: On behalf of INSU Acquisition Corp. II, a Delaware corporation (the ?Company?), we

December 31, 2020 EX-10.18

Forms of Option Agreement, Stock Option Grant Notice and Notice of Exercise under the Metromile, Inc. Amended and Restated 2011 Equity Incentive Plan (incorporated by reference to Exhibit 10.18 to the Company’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on December 31, 2021).

Exhibit 10.18 METROMILE, INC. 2011 EQUITY INCENTIVE PLAN STOCK OPTION AGREEMENT — EARLY EXERCISE Unless otherwise defined herein, the terms defined in the 2011 Equity Incentive Plan (the “Plan”) shall have the same defined meanings in this Stock Option Agreement – Early Exercise (the “Option Agreement”). I. NOTICE OF STOCK OPTION GRANT Name: Address: The undersigned Participant has been granted an

December 31, 2020 S-4/A

Form of Certificate of Amendment of Amended and Restated Certificate of Incorporation (included as Annex D to the proxy statement/prospectus).

As filed with the Securities and Exchange Commission on December 31, 2020 Registration No.

December 31, 2020 EX-3.5

Form of Second Amended and Restated Bylaws.†

Exhibit 3.5 AMENDED AND RESTATED BYLAWS OF METROMILE, INC. (A DELAWARE CORPORATION) ARTICLE I OFFICES Section 1. Registered Office. The registered office of the corporation in the State of Delaware shall be as set forth in the Certificate of Incorporation. Section 2. Other Offices. The corporation shall also have and maintain an office or principal place of business at such place as may be fixed b

December 31, 2020 EX-10.17

Metromile, Inc. Amended and Restated 2011 Equity Incentive Plan, as amended (incorporated by reference to Exhibit 10.17 to the Company’s Registration Statement on Form S-4/A, filed with the Securities and Exchange Commission on December 31, 2021).

Exhibit 10.17 METROMILE, INC. 2011 EQUITY INCENTIVE PLAN 1. Purposes of the Plan. The purposes of this Plan are: ● to attract and retain the best available personnel for positions of substantial responsibility, ● to provide additional incentive to Employees, Directors and Consultants, and ● to promote the success of the Company’s business. The Plan permits the grant of Incentive Stock Options, Non

December 16, 2020 EX-99.1

All materials are confidential and property of 1

Exhibit 99.1 All materials are confidential and property of 1 Disclaimer 2 All materials are property of This presentation is provided for informational purposes only and has been prepared to assist interested parties in making their own evaluation with respect to a potential business combination (the “ proposed business combination ” ) between MetroMile, Inc. ( “ Metromile ” ) and INSU Acquisitio

December 16, 2020 EX-99.2

Metromile Raises Policies in Force and Contribution Profit Expectations for Full Year 2020, Provides Update on Third Quarter 2020 Financial Metrics and Reaffirms Outlook for 2021-2024

Exhibit 99.2 Metromile Raises Policies in Force and Contribution Profit Expectations for Full Year 2020, Provides Update on Third Quarter 2020 Financial Metrics and Reaffirms Outlook for 2021-2024 - 2020 Year-End Policies in Force Projected to be 92,253 vs. 91,944 Prior Forecast - - Full Year 2020 Contribution Profit Forecast Now $14.1M vs. $11.3M Prior Forecast - - Full Year 2020 Loss Ratio Forec

December 16, 2020 EX-99.1

All materials are confidential and property of 1

Exhibit 99.1 All materials are confidential and property of 1 Disclaimer 2 All materials are property of This presentation is provided for informational purposes only and has been prepared to assist interested parties in making their own evaluation with respect to a potential business combination (the “ proposed business combination ” ) between MetroMile, Inc. ( “ Metromile ” ) and INSU Acquisitio

December 16, 2020 EX-99.2

Metromile Raises Policies in Force and Contribution Profit Expectations for Full Year 2020, Provides Update on Third Quarter 2020 Financial Metrics and Reaffirms Outlook for 2021-2024

Exhibit 99.2 Metromile Raises Policies in Force and Contribution Profit Expectations for Full Year 2020, Provides Update on Third Quarter 2020 Financial Metrics and Reaffirms Outlook for 2021-2024 - 2020 Year-End Policies in Force Projected to be 92,253 vs. 91,944 Prior Forecast - - Full Year 2020 Contribution Profit Forecast Now $14.1M vs. $11.3M Prior Forecast - - Full Year 2020 Loss Ratio Forec

December 16, 2020 425

Merger Prospectus - CURRENT REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 16, 2020 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation

December 16, 2020 8-K

Regulation FD Disclosure, Financial Statements and Exhibits - CURRENT REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 16, 2020 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation

November 27, 2020 S-4

Power of Attorney (included on the signature page to the initial filing of the Registration Statement).†

As filed with the Securities and Exchange Commission on November 25, 2020 Registration No.

November 27, 2020 EX-21.1

Subsidiaries of the Registrant.†

Exhibit 21.1 Subsidiaries of INSU Acquisition Corp. II INSU II Merger Sub Corp.

November 25, 2020 425

Merger Prospectus - FORM 425

Filed by Insurance Acquisition Corp. II pursuant to Rule 425 under the Securities Act of 1933, as amended, and deemed filed pursuant to Rule 14a-12 under the Securities Exchange Act of 1934, as amended Subject Company: Insurance Acquisition Corp. II Commission File No.: 001-39484 Below is a transcript of an excerpt of the November 25, 2020 episode of the “All-In with Chamath, Jason, Sacks & Friedb

November 24, 2020 EX-10.1

Sponsor Share Cancellation and Vesting Agreement, dated November 24, 2020, by and among the Company, Insurance Acquisition Sponsor II, LLC and Dioptra Advisors II, LLC (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on November 24, 2020).

Exhibit 10.1 SPONSOR SHARE CANCELLATION AND VESTING AGREEMENT This SPONSOR SHARE CANCELLATION AND VESTING AGREEMENT (this “Agreement”) is dated as of November 24, 2020, by and among INSU Acquisition Corp. II, a Delaware corporation (“Parent”), Insurance Acquisition Sponsor II, LLC, a Delaware limited liability company (“Sponsor II”), and Dioptra Advisors II, LLC, a Delaware limited liability compa

November 24, 2020 EX-99.2

METROMILE, A LEADING DIGITAL INSURANCE PLATFORM, TO BECOME PUBLIC COMPANY Metromile and INSU Acquisition Corp. II (NASDAQ: INAQ) Enter Business Combination Agreement Transaction Includes Commitment for $160 Million PIPE Led by Social Capital, Joined

Exhibit 99.2 METROMILE, A LEADING DIGITAL INSURANCE PLATFORM, TO BECOME PUBLIC COMPANY Metromile and INSU Acquisition Corp. II (NASDAQ: INAQ) Enter Business Combination Agreement Transaction Includes Commitment for $160 Million PIPE Led by Social Capital, Joined by Investors Including Miller Value, Clearbridge, Hudson Structured, Mark Cuban, and New Enterprise Associates Metromile Expanding to 49

November 24, 2020 EX-10.6

Form of Amended and Restated Registration Rights Agreement, incorporated by reference to Exhibit 10.6 to the Current Report on Form 8-K filed on November 24, 2020.

Exhibit 10.6 AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT THIS AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT (this “Agreement”), dated as of [●], 2021, is made and entered into by and among each of INSU Acquisition Corp. II, a Delaware corporation (the “Company”), Insurance Acquisition Sponsor II, LLC, a Delaware limited liability company, Dioptra Advisors II, LLC, a Delaware limited li

November 24, 2020 EX-10.4

Form of Lock-Up Agreement (incorporated by reference to Exhibit 10.4 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on November 24, 2020).

Exhibit 10.4 November [●], 2020 INSU Acquisition Corp. II 2929 Arch Street, Suite 1704 Philadelphia, PA 19104 Ladies and Gentlemen: This letter agreement (this “Letter Agreement”), by and among INSU Acquisition Corp. II, a Delaware corporation (the “Company”), and certain stockholders of MetroMile, Inc., a Delaware corporation (“Metromile”), identified on the signature pages hereto, who are intend

November 24, 2020 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits - CURRENT REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 24, 2020 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation

November 24, 2020 EX-10.3

Sponsor Support Agreement, dated November 24, 2020, by and among the Company, Insurance Acquisition Sponsor II, LLC, Dioptra Advisors II, LLC, Metromile, Inc. and the officers and directors of the Company (incorporated by reference to Exhibit 10.3 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on November 24, 2020).

Exhibit 10.3 SPONSOR SUPPORT AGREEMENT This SPONSOR SUPPORT AGREEMENT (this “Agreement”) is dated as of November 24, 2020, by and among MetroMile, Inc., a Delaware corporation (the “Company”), Insurance Acquisition Sponsor II, LLC, a Delaware limited liability company (“Insurance Sponsor”), Dioptra Advisors II, LLC, a Delaware limited liability company (each, a “Sponsor” and, together with Insuran

November 24, 2020 EX-2.1

Agreement and Plan of Merger and Reorganization, dated November 24, 2020, by and among INSU Acquisition Corp. II, INSU II Merger Sub Corp., and Metromile, Inc. (included as Annex A to the proxy statement/prospectus).+

Exhibit 2.1 EXECUTION VERSION AGREEMENT AND PLAN OF MERGER AND REORGANIZATION by and among INSU ACQUISITION CORP. II, INSU II MERGER SUB CORP., AND METROMILE, INC. DATED AS OF NOVEMBER 24, 2020 Table of Contents Page Article I CERTAIN DEFINITIONS 3 Section 1.1 Certain Definitions 3 Section 1.2 Interpretation 15 Section 1.3 Further Definitions 16 Article II THE MERGER 18 Section 2.1 The Merger 18 S

November 24, 2020 EX-10.5

Form of Subscription Agreement by and among the Company and certain subscribers (incorporated by reference to Exhibit 10.5 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on November 24, 2020).

Exhibit 10.5 SUBSCRIPTION AGREEMENT This SUBSCRIPTION AGREEMENT (this “Subscription Agreement”) is entered into on November , 2020, by and among INSU Acquisition Corp. II, a Delaware corporation (the “Issuer”), and the subscriber party set forth on the signature page hereto (“Subscriber”). WHEREAS, the Issuer is concurrently with the execution and delivery hereof entering into an Agreement and Pla

November 24, 2020 EX-99.1

Investor Presentation

Exhibit 99.1

November 24, 2020 EX-99.3

PROJECT CAMARO PRE-RECORD CALL SCRIPT

Exhibit 99.3 PROJECT CAMARO PRE-RECORD CALL SCRIPT 11-22-20 Safe Harbor: [Speaker]: Good day, ladies and gentlemen, and thank you for standing by. The Company refers participants on this call to the press release issued by the company, the presentation, and INSU Acquisition Corp. II’s filings with the SEC for a discussion of the risks that can affect the business combination, our business, and the

November 24, 2020 EX-10.2

Form of Stockholder Support Agreement by and among the Company, Metromile, Inc. and the Persons set forth on Schedule I thereto (incorporated by reference to Exhibit 10.2 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on November 24, 2020).

Exhibit 10.2 STOCKHOLDER SUPPORT AGREEMENT This STOCKHOLDER SUPPORT AGREEMENT (this “Agreement”) is dated as of November [●], 2020, by and among INSU Acquisition Corp. II, a Delaware corporation (“Parent”), the Persons set forth on Schedule I hereto (each, a “Stockholder” and, collectively, the “Stockholders”), and MetroMile, Inc., a Delaware corporation (the “Company”). Capitalized terms used but

November 24, 2020 EX-99.2

METROMILE, A LEADING DIGITAL INSURANCE PLATFORM, TO BECOME PUBLIC COMPANY Metromile and INSU Acquisition Corp. II (NASDAQ: INAQ) Enter Business Combination Agreement Transaction Includes Commitment for $160 Million PIPE Led by Social Capital, Joined

Exhibit 99.2 METROMILE, A LEADING DIGITAL INSURANCE PLATFORM, TO BECOME PUBLIC COMPANY Metromile and INSU Acquisition Corp. II (NASDAQ: INAQ) Enter Business Combination Agreement Transaction Includes Commitment for $160 Million PIPE Led by Social Capital, Joined by Investors Including Miller Value, Clearbridge, Hudson Structured, Mark Cuban, and New Enterprise Associates Metromile Expanding to 49

November 24, 2020 EX-10.5

Form of PIPE Subscription Agreement

Exhibit 10.5 SUBSCRIPTION AGREEMENT This SUBSCRIPTION AGREEMENT (this “Subscription Agreement”) is entered into on November , 2020, by and among INSU Acquisition Corp. II, a Delaware corporation (the “Issuer”), and the subscriber party set forth on the signature page hereto (“Subscriber”). WHEREAS, the Issuer is concurrently with the execution and delivery hereof entering into an Agreement and Pla

November 24, 2020 EX-10.1

Sponsor Share Cancellation and Vesting Agreement, dated November 24, 2020, by and among INSU Acquisition Corp. II, Insurance Acquisition Sponsor II, LLC and Dioptra Advisors II, LLC.

Exhibit 10.1 SPONSOR SHARE CANCELLATION AND VESTING AGREEMENT This SPONSOR SHARE CANCELLATION AND VESTING AGREEMENT (this “Agreement”) is dated as of November 24, 2020, by and among INSU Acquisition Corp. II, a Delaware corporation (“Parent”), Insurance Acquisition Sponsor II, LLC, a Delaware limited liability company (“Sponsor II”), and Dioptra Advisors II, LLC, a Delaware limited liability compa

November 24, 2020 EX-10.3

Sponsor Support Agreement dated November 24, 2020, by and among INSU Acquisition Corp. II, Insurance Acquisition Sponsor II, LLC, Dioptra Advisors II, LLC, MetroMile, Inc. and the officers and directors of INSU Acquisition Corp. II

Exhibit 10.3 SPONSOR SUPPORT AGREEMENT This SPONSOR SUPPORT AGREEMENT (this “Agreement”) is dated as of November 24, 2020, by and among MetroMile, Inc., a Delaware corporation (the “Company”), Insurance Acquisition Sponsor II, LLC, a Delaware limited liability company (“Insurance Sponsor”), Dioptra Advisors II, LLC, a Delaware limited liability company (each, a “Sponsor” and, together with Insuran

November 24, 2020 EX-10.4

Form of Lock-Up Agreement

Exhibit 10.4 November [●], 2020 INSU Acquisition Corp. II 2929 Arch Street, Suite 1704 Philadelphia, PA 19104 Ladies and Gentlemen: This letter agreement (this “Letter Agreement”), by and among INSU Acquisition Corp. II, a Delaware corporation (the “Company”), and certain stockholders of MetroMile, Inc., a Delaware corporation (“Metromile”), identified on the signature pages hereto, who are intend

November 24, 2020 EX-99.1

Investor Presentation

Exhibit 99.1

November 24, 2020 EX-2.1

Agreement and Plan of Merger and Reorganization, dated November 24, 2020, by and among INSU Acquisition Corp. II, INSU II Merger Sub Corp. and MetroMile, Inc.*

Exhibit 2.1 EXECUTION VERSION AGREEMENT AND PLAN OF MERGER AND REORGANIZATION by and among INSU ACQUISITION CORP. II, INSU II MERGER SUB CORP., AND METROMILE, INC. DATED AS OF NOVEMBER 24, 2020 Table of Contents Page Article I CERTAIN DEFINITIONS 3 Section 1.1 Certain Definitions 3 Section 1.2 Interpretation 15 Section 1.3 Further Definitions 16 Article II THE MERGER 18 Section 2.1 The Merger 18 S

November 24, 2020 EX-99.3

PROJECT CAMARO PRE-RECORD CALL SCRIPT

Exhibit 99.3 PROJECT CAMARO PRE-RECORD CALL SCRIPT 11-22-20 Safe Harbor: [Speaker]: Good day, ladies and gentlemen, and thank you for standing by. The Company refers participants on this call to the press release issued by the company, the presentation, and INSU Acquisition Corp. II’s filings with the SEC for a discussion of the risks that can affect the business combination, our business, and the

November 24, 2020 EX-10.6

Form of Registration Rights Agreement

Exhibit 10.6 AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT THIS AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT (this “Agreement”), dated as of [●], 2021, is made and entered into by and among each of INSU Acquisition Corp. II, a Delaware corporation (the “Company”), Insurance Acquisition Sponsor II, LLC, a Delaware limited liability company, Dioptra Advisors II, LLC, a Delaware limited li

November 24, 2020 EX-10.2

Form of Stockholder Support Agreement by and among INSU Acquisition Corp. II, MetroMile, Inc. and the Persons set forth on Schedule I thereto.

Exhibit 10.2 STOCKHOLDER SUPPORT AGREEMENT This STOCKHOLDER SUPPORT AGREEMENT (this “Agreement”) is dated as of November [●], 2020, by and among INSU Acquisition Corp. II, a Delaware corporation (“Parent”), the Persons set forth on Schedule I hereto (each, a “Stockholder” and, collectively, the “Stockholders”), and MetroMile, Inc., a Delaware corporation (the “Company”). Capitalized terms used but

November 24, 2020 425

Merger Prospectus - CURRENT REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 24, 2020 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation

November 14, 2020 10-Q

Quarterly Report - QUARTERLY REPORT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2020 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File No. 001-39484 INSU ACQUISI

September 16, 2020 SC 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* INSU Acquisition Corp. II (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Cl

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* INSU Acquisition Corp. II (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 457821304 (CUSIP Number) September 8, 2020 (Date of Event which Requires Filing of this Statement) Check the appropriate box to des

September 16, 2020 EX-99.A

JOINT FILING AGREEMENT

Page 10 of 10 EXHIBIT A JOINT FILING AGREEMENT The undersigned hereby agree that the statement on Schedule 13G with respect to the Class A common stock of INSU Acquisition Corp.

September 14, 2020 EX-99.1

INDEX TO FINANCIAL STATEMENT

Exhibit 99.1 INDEX TO FINANCIAL STATEMENT Audited Financial Statements for INSU Acquisition Corp. II: Page Report of Independent Registered Public Accounting Firm F-2 Balance Sheet as of September 8, 2020 F-3 Notes to Financial Statement F-4 F-1 Report of Independent Registered Public Accounting Firm Board of Directors and Shareholders INSU Acquisition Corp. II Opinion on the Financial Statement W

September 14, 2020 SC 13G

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G (RULE 13d - 102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO 13d-1(b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO 13d-2(b) (Amendment No. )* Insu Acquisit

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G (RULE 13d - 102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO 13d-1(b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO 13d-2(b) (Amendment No. )* Insu Acquisition Corp. II (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 457821304** (CUSIP Number) September 3,

September 14, 2020 8-K

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 8, 2020 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation

September 10, 2020 SC 13G

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 INSU ACQUISITION CORP. II (Name of Issuer) CLASS A COMMON STOCK, PAR VALUE $0.0001 PER SHARE (Title of Class of Securities)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 INSU ACQUISITION CORP. II (Name of Issuer) CLASS A COMMON STOCK, PAR VALUE $0.0001 PER SHARE (Title of Class of Securities) 457821304 (CUSIP Number) SEPTEMBER 3, 2020 (Date of event which requires filing of this statement) Check the appropriate box to designate the rule pu

September 9, 2020 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Material Modification to Rights of Security Holders, Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 2, 2020 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 001-39484 84-4916134 (State or other jurisdiction of incorporation

September 9, 2020 EX-1.1

Underwriting Agreement, dated September 2, 2020, between the Company and Cantor Fitzgerald & Co., incorporated by reference to Exhibit 1.1 to the Current Report on Form 8-K filed on September 9, 2020.

Exhibit 1.1 UNDERWRITING AGREEMENT between INSU ACQUISITION CORP. II and CANTOR FITZGERALD & CO. Dated: September 2, 2020 INSU ACQUISITION CORP. II UNDERWRITING AGREEMENT New York, New York September 2, 2020 Cantor Fitzgerald & Co. 499 Park Avenue New York, New York 10022 As Representative of the Several Underwriters named on Schedule A hereto Ladies and Gentlemen: The undersigned, INSU Acquisitio

September 9, 2020 EX-10.7

Loan Commitment Agreement, dated September 2, 2020, by and between the Company and Insurance Acquisition Sponsor II, LLC (incorporated by reference to Exhibit 10.7 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on September 9, 2020).

Exhibit 10.7 INSU Acquisition Corp. II 2929 Arch Street, Suite 1703 Philadelphia, PA 19104-2870 Attention: Joseph W. Pooler, Jr. Dated: September 2, 2020 Insurance Acquisition Sponsor II, LLC (?Lender?) hereby agrees to make to INSU Acquisition Corp. II (?Borrower?), one or more loans for the purposes described in paragraph 2 hereof, in amounts and upon the terms and conditions set forth below: 1.

September 9, 2020 EX-10.2

Investment Management Trust Agreement, dated September 2, 2020, by and between the Company and Continental Stock Transfer & Trust Company (incorporated by reference to Exhibit 10.2 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on September 9, 2020).

Exhibit 10.2 INVESTMENT MANAGEMENT TRUST AGREEMENT This Investment Management Trust Agreement (this ?Agreement?) is made effective as of September 2, 2020 by and between INSU Acquisition Corp. II, a Delaware corporation (the ?Company?), and Continental Stock Transfer & Trust Company, a New York corporation (the ?Trustee?). WHEREAS, the Company?s registration statement on Form S-1, No. 333-240205 (

September 9, 2020 EX-3.1

Amended and Restated Certificate of Incorporation, filed with the Secretary of State of the State of Delaware on September 3, 2020, incorporated by reference to Exhibit 3.1 to the Current Report on Form 8-K filed on September 9, 2020.

Exhibit 3.1 AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF INSU ACQUISITION CORP. II INSU Acquisition Corp. II, a corporation organized and existing under the laws of the State of Delaware (the ?Corporation?), DOES HEREBY CERTIFY AS FOLLOWS: 1. The name of the Corporation is ?INSU Acquisition Corp. II? The original certificate of incorporation under the name of ?HC Merger Corp.? was filed wi

September 9, 2020 EX-10.4

Unit Subscription Agreement, dated September 2, 2020, by and between the Company and Insurance Acquisition Sponsor II, LLC (incorporated by reference to Exhibit 10.4 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on September 9, 2020).

Exhibit 10.4 UNIT SUBSCRIPTION AGREEMENT This UNIT SUBSCRIPTION AGREEMENT (this ?Agreement?) is made as of the 2nd day of September, 2020, by and between INSU Acquisition Corp. II, a Delaware corporation (the ?Company?), having its principal place of business at 2929 Arch Street, Suite 1703, Philadelphia, PA 19104, and the subscribers set forth on Schedule A hereto (the ?Subscribers?). WHEREAS, th

September 9, 2020 EX-10.1

Letter Agreement, dated September 2, 2020, by and between the Company and certain security holders, officers, and directors of the Company (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on September 9, 2020).

Exhibit 10.1 September 2, 2020 INSU Acquisition Corp. II 2929 Arch Street, Suite 1703 Philadelphia, PA 19104-2870 Re: Initial Public Offering Ladies and Gentlemen: This letter (“Letter Agreement”) is being delivered to you in accordance with the Underwriting Agreement (the “Underwriting Agreement”) entered into, or proposed to be entered into, by and between INSU Acquisition Corp. II, a Delaware c

September 9, 2020 EX-99.1

INSU Acquisition Corp. II Announces Pricing of Upsized $200,000,000 Initial Public Offering

Exhibit 99.1 INSU Acquisition Corp. II Announces Pricing of Upsized $200,000,000 Initial Public Offering PHILADELPHIA, PA, September 2, 2020 (Globe Newswire) - INSU Acquisition Corp. II (NASDAQ:INAQU) (the ?Company?), a blank-check company formed for the purpose of acquiring or merging with one or more businesses or entities in the insurance industry, today announced the pricing of its upsized ini

September 9, 2020 EX-99.2

Cohen & Company and INSU Acquisition Corp. II Announce Completion of INSU Acquisition Corp. II $230,000,000 Initial Public Offering, Including Full Exercise of Over-Allotment Option

Exhibit 99.2 Cohen & Company and INSU Acquisition Corp. II Announce Completion of INSU Acquisition Corp. II $230,000,000 Initial Public Offering, Including Full Exercise of Over-Allotment Option PHILADELPHIA, PA, September 8, 2020 (GLOBE NEWSWIRE) – Cohen & Company Inc. (NYSE American: COHN) and INSU Acquisition Corp. II (NASDAQ:INAQU) today announced that INSU Acquisition Corp. II (the “Company”)

September 9, 2020 EX-10.5

Unit Subscription Agreement, dated September 2, 2020, by and between the Company and Cantor Fitzgerald & Co. (incorporated by reference to Exhibit 10.5 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on September 9, 2020).

Exhibit 10.5 UNIT SUBSCRIPTION AGREEMENT This UNIT SUBSCRIPTION AGREEMENT (this “Agreement”) is made as of the 2nd day of September, 2020, by and between INSU Acquisition Corp. II, a Delaware corporation (the “Company”), having its principal place of business at 2929 Arch Street, Suite 1703, Philadelphia, PA 19104, and Cantor Fitzgerald & Co., a New York general partnership (“Subscriber”), having

September 9, 2020 EX-10.6

Administrative Services Agreement, dated September 2, 2020, by and between the Company and Cohen & Company, LLC (incorporated by reference to Exhibit 10.6 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on September 9, 2020).

Exhibit 10.6 INSU ACQUISITION CORP. II 2929 Arch Street, Suite 1703 Philadelphia, PA 19104 September 2, 2020 Cohen & Company, LLC 2929 Arch Street, Suite 1703 Philadelphia, PA 19104 Re: Administrative Services Agreement Gentlemen: This letter agreement by and between INSU Acquisition Corp. II (the ?Company?) and Cohen & Company, LLC (?Cohen?), dated as of the date hereof, will confirm our agreemen

September 9, 2020 EX-4.1

Warrant Agreement, dated September 2, 2020, between INSU Acquisition Corp. II and Continental Stock Transfer & Trust Company, as warrant agent

Exhibit 4.1 WARRANT AGREEMENT THIS WARRANT AGREEMENT (this ?Agreement?), dated as of September 2, 2020, is by and between INSU Acquisition Corp. II, a Delaware corporation (the ?Company?), and Continental Stock Transfer & Trust Company, a New York limited purpose trust company, as warrant agent (the ?Warrant Agent?; also referred to as the ?Transfer Agent?). WHEREAS, the Company has entered into t

September 9, 2020 EX-10.3

Registration Rights Agreement, dated September 2, 2020, by and among the Company and certain security holders of the Company (incorporated by reference to Exhibit 10.3 to the Company’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on September 9, 2020).

Exhibit 10.3 REGISTRATION RIGHTS AGREEMENT THIS REGISTRATION RIGHTS AGREEMENT (this ?Agreement?), dated as of September 2, 2020, is made and entered into by and among each of INSU Acquisition Corp. II, a Delaware corporation (the ?Company?), Insurance Acquisition Sponsor II, LLC, a Delaware limited liability company, and Dioptra Advisors II, LLC, a Delaware limited liability company (collectively,

September 4, 2020 424B4

$200,000,000 INSU Acquisition Corp. II 20,000,000 Units

PROSPECTUS Filed pursuant to Rule 424(b)(4) Registration No. 333-240205 Registration No. 333-248567 $200,000,000 INSU Acquisition Corp. II 20,000,000 Units INSU Acquisition Corp. II is a blank check company that will seek to effect a merger, capital stock exchange, asset acquisition, stock purchase, reorganization or similar business combination with one or more businesses, which we refer to throu

September 2, 2020 8-A12B

- FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR (g) OF THE SECURITIES EXCHANGE ACT OF 1934 INSU ACQUISITION CORP. II (Exact Name of Registrant as Specified in Its Charter) Delaware 84-4916134 (State or other Jurisdiction of Incorporation or Organization) (I.R.S. Employer Identification N

September 2, 2020 S-1MEF

- REGISTRATION STATEMENT

As filed with the Securities and Exchange Commission on September 2, 2020 Registration No.

September 1, 2020 CORRESP

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September 1, 2020 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.

August 31, 2020 CORRESP

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INSU Acquisition Corp. II 2929 Arch Street, Suite 1703 Philadelphia, PA 19104-2870 August 31, 2020 VIA EDGAR Erin E. Martin Office of Real Estate & Construction 100 F Street, N. E. Securities and Exchange Commission Washington, D.C. 20549 Re: INSU Acquisition Corp. II Registration Statement on Form S-1 Filed July 30, 2020, as amended File No. 333-240205 Dear Ms. Martin: Pursuant to Rule 461 under

August 28, 2020 CORRESP

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August 28, 2020 VIA EDGAR TRANSMISSION U.S. Securities and Exchange Commission Division of Corporation Finance Office of Real Estate & Construction 100 F Street NE Washington, D.C. 20549 Re: INSU Acquisition Corp. II Amendment No. 2 to Registration Statement on Form S-1 Filed August 27, 2020 File No. 333-240205 Ladies and Gentlemen: On behalf of INSU Acquisition Corp. II, a Delaware corporation (t

August 28, 2020 S-1/A

- AMENDMENT NO. 3 TO FORM S-1

As filed with the U.S. Securities and Exchange Commission on August 28, 2020. Registration No. 333-240205 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDMENT NO. 3 TO FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 6770 84-4916134 (State or other jurisdiction of

August 27, 2020 EX-4.1

Specimen Unit Certificate, incorporated by reference to Exhibit 4.1 to Amendment No. 2 to the Registration Statement on Form S-1 filed on August 27, 2020.

Exhibit 4.1 SPECIMEN UNIT CERTIFICATE [] UNITS U-[●] SEE REVERSE FOR CERTAIN DEFINITIONS CUSIP [ ] INSU ACQUISITION CORP. II UNITS CONSISTING OF ONE SHARE OF CLASS A COMMON STOCK AND ONE THIRD WARRANT TO PURCHASE ONE SHARE OF CLASS A COMMON STOCK THIS CERTIFIES THAT is the owner of Units. Each Unit (“Unit”) consists of one (1) share of Class A common stock, $0.0001 par value per share (the “Common

August 27, 2020 EX-10.3(B)

Form of Placement Unit Subscription Agreement with Cantor Fitzgerald & Co.*

Exhibit 10.3 (b) FORM OF UNIT SUBSCRIPTION AGREEMENT This UNIT SUBSCRIPTION AGREEMENT (this “Agreement”) is made as of the day of 2020, by and between INSU Acquisition Corp. II, a Delaware corporation (the “Company”), having its principal place of business at 2929 Arch Street, Suite 1703, Philadelphia, PA 19104, and Cantor Fitzgerald & Co., a New York general partnership (“Subscriber”), having its

August 27, 2020 EX-10.4

Form of Letter Agreement by and between the Registrant, the Registrant’s security holders named therein, and the officers and directors of the Registrant.*

Exhibit 10.4 , 2020 INSU Acquisition Corp. II 2929 Arch Street, Suite 1703 Philadelphia, PA 19104-2870 Re: Initial Public Offering Ladies and Gentlemen: This letter (“Letter Agreement”) is being delivered to you in accordance with the Underwriting Agreement (the “Underwriting Agreement”) entered into, or proposed to be entered into, by and between INSU Acquisition Corp. II, a Delaware corporation

August 27, 2020 EX-10.3(A)

Form of Placement Unit Subscription Agreement with Insurance Acquisition Sponsor II, LLC.*

Exhibit 10.3 (a) FORM OF UNIT SUBSCRIPTION AGREEMENT This UNIT SUBSCRIPTION AGREEMENT (this “Agreement”) is made as of the day of 2020, by and between INSU Acquisition Corp. II, a Delaware corporation (the “Company”), having its principal place of business at 2929 Arch Street, Suite 1703, Philadelphia, PA 19104, and the subscribers set forth on Schedule A hereto (the “Subscribers”). WHEREAS, the C

August 27, 2020 EX-4.2

Specimen Common Stock Certificate, incorporated by reference to Exhibit 4.2 to Amendment No. 2 to the Registration Statement on Form S-1 filed on August 27, 2020.

Exhibit 4.2 NUMBER SHARES SEE REVERSE FOR CERTAIN DEFINITIONS CUSIP [ ] INSU ACQUISITION CORP. II A DELAWARE CORPORATION CLASS A COMMON STOCK This Certifies that is the owner of FULLY PAID AND NON-ASSESSABLE SHARES OF CLASS A COMMON STOCK, $0.0001 PAR VALUE PER SHARE EACH, OF INSU ACQUISITION CORP. II (THE “CORPORATION”) transferable on the books of the Corporation in person or by duly authorized

August 27, 2020 EX-10.8

Form of Promissory Note for working capital loan from Insurance Acquisition Sponsor II, LLC to the Registrant (included in Exhibit 10.8).*

Exhibit 10.8 INSU Acquisition Corp. II 2929 Arch Street, Suite 1703 Philadelphia, PA 19104-2870 Attention: Joseph W. Pooler, Jr. Dated: , 2020 Insurance Acquisition Sponsor II, LLC (“Lender”) hereby agrees to make to INSU Acquisition Corp. II (“Borrower”), one or more loans for the purposes described in paragraph 2 hereof, in amounts and upon the terms and conditions set forth below: 1. AMOUNT Len

August 27, 2020 EX-3.1(E)

Form of Amended and Restated Certificate of Incorporation.*

Exhibit 3.1(e) FORM OF AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF INSU ACQUISITION CORP. II INSU Acquisition Corp. II, a corporation organized and existing under the laws of the State of Delaware (the “Corporation”), DOES HEREBY CERTIFY AS FOLLOWS: 1. The name of the Corporation is “INSU Acquisition Corp. II” The original certificate of incorporation was filed with the Secretary of State

August 27, 2020 EX-99.6

Consent of Andrew Hohns*

Exhibit 99.6 CONSENT OF TO BE NAMED AS A DIRECTOR NOMINEE INSU Acquisition Corp. II intends to file a Registration Statement on Form S-1 (together with any amendments or supplements thereto, the “Registration Statement”) registering securities for issuance in its initial public offering. As required by Rule 438 under the Securities Act of 1933, as amended, the undersigned hereby consents to being

August 27, 2020 EX-4.4

Specimen Warrant Certificate (included in Exhibit 4.4), incorporated by reference to Exhibit 4.4 to Amendment No. 2 to the Registration Statement on Form S-1 filed on August 27, 2020.

EX-4.4 5 fs12020a2ex4-4insuacqu.htm FORM OF WARRANT AGREEMENT BETWEEN CONTINENTAL STOCK TRANSFER & TRUST COMPANY AND THE REGISTRANT Exhibit 4.4 FORM OF WARRANT AGREEMENT THIS WARRANT AGREEMENT (this “Agreement”), dated as of , 2020, is by and between INSU Acquisition Corp. II, a Delaware corporation (the “Company”), and Continental Stock Transfer & Trust Company, a New York corporation, as warrant

August 27, 2020 CORRESP

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August 27, 2020 VIA EDGAR TRANSMISSION U.S. Securities and Exchange Commission Division of Corporation Finance Office of Real Estate & Construction 100 F Street NE Washington, D.C. 20549 Re: INSU Acquisition Corp. II Amendment No. 1 to Registration Statement on Form S-1 Filed August 25, 2020 File No. 333-240205 Ladies and Gentlemen: On behalf of INSU Acquisition Corp. II, a Delaware corporation (t

August 27, 2020 EX-10.1

Form of Investment Management Trust Agreement between Continental Stock Transfer & Trust Company and the Registrant.*

Exhibit 10.1 INVESTMENT MANAGEMENT TRUST AGREEMENT This Investment Management Trust Agreement (this “Agreement”) is made effective as of , 2020 by and between INSU Acquisition Corp. II, a Delaware corporation (the “Company”), and Continental Stock Transfer & Trust Company, a New York corporation (the “Trustee”). WHEREAS, the Company’s registration statement on Form S-1, No. 333-240205 (the “Regist

August 27, 2020 S-1/A

- AMENDMENT NO. 2 TO FORM S-1

As filed with the U.S. Securities and Exchange Commission on August 27, 2020. Registration No. 333-240205 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDMENT NO. 2 TO FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 6770 84-4916134 (State or other jurisdiction of

August 25, 2020 S-1/A

- AMENDMENT NO. 1 TO FORM S-1

As filed with the U.S. Securities and Exchange Commission on August 24, 2020. Registration No. 333-240205 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDMENT NO. 1 TO FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 INSU ACQUISITION CORP. II (Exact name of registrant as specified in its charter) Delaware 6770 84-4916134 (State or other jurisdiction of

August 25, 2020 EX-1.1

Form of Underwriting Agreement.**

Exhibit 1.1 UNDERWRITING AGREEMENT between INSU ACQUISITION CORP. II and CANTOR FITZGERALD & CO. Dated: August [ ], 2020 INSU ACQUISITION CORP. II UNDERWRITING AGREEMENT New York, New York August [ ], 2020 Cantor Fitzgerald & Co. 499 Park Avenue New York, New York 10022 As Representative of the Several Underwriters named on Schedule A hereto Ladies and Gentlemen: The undersigned, INSU Acquisition

August 25, 2020 EX-10.4

Form of Letter Agreement by and between the Registrant, the Registrant’s security holders named therein, and the officers and directors of the Registrant.*

Exhibit 10.4 , 2020 INSU Acquisition Corp. II 2929 Arch Street, Suite 1703 Philadelphia, PA 19104-2870 Re: Initial Public Offering Ladies and Gentlemen: This letter (“Letter Agreement”) is being delivered to you in accordance with the Underwriting Agreement (the “Underwriting Agreement”) entered into, or proposed to be entered into, by and between INSU Acquisition Corp. II, a Delaware corporation

August 25, 2020 EX-10.1

Form of Investment Management Trust Account Agreement between Continental Stock Transfer & Trust Company and the Registrant.*

Exhibit 10.1 INVESTMENT MANAGEMENT TRUST AGREEMENT This Investment Management Trust Agreement (this “Agreement”) is made effective as of , 2020 by and between INSU Acquisition Corp. II, a Delaware corporation (the “Company”), and Continental Stock Transfer & Trust Company, a New York corporation (the “Trustee”). WHEREAS, the Company’s registration statement on Form S-1, No. 333-240205 (the “Regist

August 25, 2020 EX-4.4

Form of Warrant Agreement between Continental Stock Transfer & Trust Company and the Registrant.*

Exhibit 4.4 FORM OF WARRANT AGREEMENT THIS WARRANT AGREEMENT (this “Agreement”), dated as of , 2020, is by and between INSU Acquisition Corp. II, a Delaware corporation (the “Company”), and Continental Stock Transfer & Trust Company, a New York corporation, as warrant agent (the “Warrant Agent”; also referred to as the “Transfer Agent”). WHEREAS, the Company has entered into those certain Unit Sub

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