Digital Insurance Summit 2025 | customer-first insurance innovation

April 28 - 29, 2025

Westin Copley Place - Boston, MA

Michael Flynn

Director of Marketing Metromile

Michael serves as the Director of Marketing and Head of Performance Marketing of Metromile, the leading pay-per-mile car insurance company in the U.S. In his current role he leads the customer acquisition, engagement, and marketing analytics teams, with responsibilities including overall sales growth for the company, market and channel strategy, and new segment exploration. Metromile is backed by leading venture capital firms and international insurers including Index Ventures, New Enterprise Associates, Intact Financial Corp., and Tokio Marine Holdings Inc. 

Michael brings expertise with digital and marketing innovation earned across the consumer finance landscape. For the past 12 years he's been building finance, analytical, and marketing programs in a number of verticals, including student loans, personal loans, marketplace lending, and P&C insurance. In addition to scaling growth at Metromile, he's consulted on marketing strategy for lending companies like OnDeck and Marlette Funding, built the marketing engine that fueled growth at Prosper Marketplace, and managed a number of finance and credit functions for College Loan Corporation.


Check out the incredible speaker line-up to see who will be joining Michael.

Download The Latest Agenda