At Metromile, we invent smarter ways to manage risk
Metromile is a leading pay-per-mile car insurance company in the U.S. Recognized by Forrester as a top insurance carrier in user experience, it is creating a loyal community of drivers with personalized insurance that is customized to each driver to be more affordable. Powered by machine learning and customer-centric design, Metromile is at the forefront of disrupting a more than $250 billion personal auto insurance industry that has gone unchanged for decades. Through Metromile Enterprise, our software-as-a-service business group, we license our proprietary artificial intelligence claims platform to automate claims, reduce losses associated with fraud, and unlock the productivity of insurance carriers’ employees so they can work on higher-impact experiences.
We’re a diverse team that combines Silicon Valley’s best technologists with veterans from Fortune 500 insurers and financial service institutions. This approach ensures that we’re as equally focused on loss ratios, unit economics and profitability as on customer experience and technology innovation.
Dan Preston Chief Executive Officer
Dan joined Metromile in 2013 as Chief Technology Officer before becoming Chief Executive Officer in 2014. Under his leadership, Metromile has experienced significant policy, premium and employee growth. The company has also established itself as the industry leader in leveraging artificial intelligence and machine learning to improve the customer experience and lower loss ratios. Metromile has been voted a Best Place to Work by Glassdoor and the Phoenix Business Journal.
Prior to joining Metromile, Dan was the co-founder and CTO of AisleBuyer, a mobile retail innovator that was acquired by Intuit in April 2012. He has published several research papers on machine learning with applications such as astrophysics, remote sensing, and computer vision.
Dan holds a master’s degree in Computer Science with a specialization in Artificial Intelligence, Machine Learning, and Computer Vision from Stanford University and a bachelor’s degree in Computer Science from Brandeis University, where he received the Michtom Prize for Outstanding Achievement in Computer Science and graduated Summa Cum Laude with highest honors in Computer Science.
Regi Vengalil Chief Financial Officer
Regi is the chief financial officer at Metromile. He is responsible for Metromile’s financial management, including financial planning and operations, treasury, investor relations, reinsurance and corporate development.
Regi joined Metromile from Egencia, Expedia Group’s corporate travel division, where he was CFO. He led the global finance team of more than 100 professionals and was responsible for the financial planning and operations, controllership and commercial finance. Before becoming CFO of Egencia, he also served as a member of Expedia Group’s executive team as global head of corporate development and strategy.
Before joining Expedia Group, he was head of strategy, M&A, and business operations at LendingClub. Earlier in his career, he led teams advising financial services and travel firms on growth and M&A at McKinsey & Company. He is also currently a board member and chair of the M&A committee of Porch Group, a home services vertical software company.
Regi holds a master of business administration and bachelor of science in economics; both earned with honors from the Wharton School of the University of Pennsylvania.
Lindsay Alexovich Chief Accounting Officer
Lindsay is the chief accounting officer at Metromile. With more than 15years of accounting and finance experience, including in the insurance-technology industry, she oversees the company’s accounting and financial reporting operations. Before joining Metromile, Lindsay was a director at PwC, where she served as the chief auditor in San Francisco. She has deep experience working with both public and high-growth private companies, leading audits, and serving as the insurance and controls subject matter expert across national and global priority accounts.
Lindsay is an alumna of American University and holds a bachelor’s with honors in mathematics and a bachelor of science in business administration with honors with an accounting specialization. She is a recipient of the Dean’s Achievement Award and the Capstone Award for the best thesis in the business school. She is a licensed CPA and member of the American Institute of Certified Public Accountants.
Junna Ro General Counsel
Junna Ro is the general counsel at Metromile. In her role, she oversees a growing team of legal, regulatory, and compliance professionals as a member of the leadership team. She is also the company’s corporate secretary.
Junna joined Metromile with more than 15 years of experience in the industry at CSAA Insurance Group. She was vice president, chief ethics and compliance officer and associate general counsel, responsible for corporate compliance and ethics, privacy, product forms, and employment law.
Before AAA, she served as corporate counsel for Symantec and its predecessor VERITAS Software for seven years. She sits on the Asian Pacific Fund’s advisory council, and on the executive committee for the National Association for Diversity in Compliance. Junna is an alumna of Santa Clara University School of Law and UCLA. She is admitted to practice law in California.
Troy Dye SVP, Growth
Troy is the Senior Vice President, Growth at Metromile. He oversees a fast-growing team of growth, acquisition, brand and marketing professionals responsible for bringing Metromile’s vision of fairer and real-time insurance to more drivers.
Troy joined Metromile with more than 20 years of experience leading disciplined, data-driven marketing machines and transforming the brands of large, data-driven and digital personal finance products. He was most recently Managing Vice President and Head of Card Marketing, Engagement and Insights for Capital One’s domestic consumer credit card business. He has also held executive roles leading marketing for Capital One’s small business credit card and partnerships divisions and the brand strategy for the U.S. credit card business and the marketing team in Canada.
Troy serves on the board of directors of NextUp, a nonprofit organization focused on providing quality after-school programs for middle school students in Richmond, Virginia. He is an alumnus of the University of Virginia and the United States Naval Academy.
Matt Stein SVP, Product
With more than twenty years of experience creating well-loved products, Matt leads Metromile’s Product, Design, and Project teams. He joined Metromile in 2015 from Salesforce, where he was Director, Product Design for the Community Cloud. Previously, he spent a decade at Autodesk, where he worked across the full spectrum of product, engineering, and design. Matt has a B. Sc. in Computer Science from the University of California at Santa Barbara.
Debra Jack SVP, Communications
Debra oversees Metromile’s corporate, consumer and internal communications. She has more than 20 years of experience working with high growth consumer companies. Serving as Metromile’s first senior head of communications, she’s held similar roles at SoFi and LendUp, two fintechs recognized for creating well-loved, disruptor brands.
Prior, she was SVP of corporate communications for Bank of the West, an $89 billion bank owned by BNP Paribas. Before moving in-house, Debra was an EVP at Edelman, the world’s largest privately held communications agency, where she ran its SF-based corporate, crisis, and social responsibility practice. She’s a graduate of SUNY Oneonta.
Jim Huscroft SVP, Claims
Jim has over 30 years of auto claims experience, including 28 years in multiple leadership roles with Progressive—most recently leading claims and special investigative teams in six states. He received his BBA and MBA from Kent State University, and also holds a CPCU designation.
Jesse McKendry SVP, Insurance
Jesse is the Senior Vice President, Insurance at Metromile. He oversees the company’s insurance product management. Jesse joined Metromile with 14 years of insurance product management and marketing experience with Progressive and has also spent nearly a decade in auto supply chain and logistics, including Daimler and General Motors.
Jesse has an MBA from The Wharton School of the University of Pennsylvania, a master’s in mechanical engineering from Stanford University, and a bachelor’s of science in mechanical engineering from Michigan State University.