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.
Paw Andersen Chief Technology Officer
Paw Andersen is a technologist with over 20 years of engineering leadership experience. He was most notably a senior leader of engineering in Uber’s Advanced Technology group, where he grew his team from 27 to 700.
Beyond ride-sharing and autonomous vehicles, he’s been on the front lines of technical challenges in several sectors, including geographic information systems, fintech and e-commerce, ranging from small startups to large, established companies.
Originally from Denmark, he is a graduate of the London Business School, Niels Brock Copenhagen Business College, and Aalborg University.
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.
Mark Gundacker Chief of Staff and Chief People Officer
Mark brings over 25 years of Human Resources experience with him as Metromile’s Chief People Officer. From his first HR role in an insurance company to his most recent in a technology firm, Mark’s experience covers the breadth of Insurtech.
Most recently, Mark was the SVP of Human Resources at Salesforce.org, the public benefit corporation for Salesforce. While there, Mark grew the organization from 300 to over 1100.
Previously, Mark led HR organizations for global engineering and finance organizations. Mark is passionate about community involvement and currently serves on three non-profit boards. He holds an MBA from Golden Gate University and a BA in Business Economics from the University of California, Santa Cruz.
Matt Stein VP, 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 VP, 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 VP, 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 VP, Insurance
Jesse is the vice president of insurance at Metromile. He oversees the company’s insurance product management and marketing efforts. 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.
Amrish Singh General Manager, Enterprise
Amrish is the general manager of Metromile Enterprise, the software-as-a-service business group of the namesake pay-per-mile car insurance leader. He joined Metromile in 2018 to launch the business group and help insurance companies around the world automate their operations, reduce losses associated with fraud, and unlock the productivity of their employees with automation and machine learning technologies.
A lifelong technologist, he has dedicated his career to helping companies operate with greater efficiency and provide a premium customer experience in the enterprise software industry. Before Metromile, he spent more than 16 years in enterprise-product, management consulting, and software engineering leadership roles, including as a founding chief technology officer of a startup and advisor to entrepreneurs, to help scale enterprise software startups.
Amrish holds an MBA from the NYU Stern School of Business, a master’s in information systems with summa cum laude honors from Carnegie Mellon University, and a bachelor’s in information technology from a German international university.