Behind the Scenes with Metromile’s New Chief Financial Officer Regi Vengalil

Regi Vengalil joined Metromile as chief financial officer. A 15-year veteran of financial planning and operations, he is excited about the opportunities ahead for Metromile.

We started Metromile because we saw an opportunity for insurance to be fairer. We believe the most powerful advantage in insurance is grounded in technology and experience, and we set out to build a better experience from Day One.

Regi Vengalil might understand this more than anyone else. In addition to his more than 15 years of experience as a financial steward, corporate development strategist, and operations executive, Regi is also a Metromile customer of six years.

It’s just one of the reasons why we’re excited Regi has joined Metromile as our chief financial officer.

Here’s why Regi decided to become a Metromiler and the opportunities he sees ahead.

What should people know about you, Regi?

I recently moved back to Seattle to spend more time with my family, and my weekends and evenings are usually spent with them. My parents live nearby, so one thing we started doing recently is to have my entire family stay one night a week at my parents’ house. Growing up in the U.S., my grandparents lived in India, so I never had the chance to spend much time with them. I’m glad my two kids have the opportunity to connect with their grandparents.

I’ve also been a Metromile customer for six years in the San Francisco Bay Area and Seattle. My family and I are huge Metromile fans.

How did you first hear about Metromile?

I used to take the subway into San Francisco, and I saw Metromile ads underground and in the station. I remember seeing the ad and thinking: This makes financial sense.

I only drove my car maybe 100 or 200 miles a month, mainly on the weekends, and I thought Metromile was perfectly designed for me. My wife has a car that she drives maybe 60 miles a month to pick up groceries and run errands. I have had such a great experience between the street-sweeping alerts, remembering where you parked from the app, and understanding how much gas is in your car. 

My wife makes fun of me, but Metromile is the type of product I’m telling people about at parties and on the weekends. Otherwise, how many times do you talk to your friends about auto insurance?

Is that why you decided to join Metromile?

I think there’s so much opportunity for Metromile. I believe we’re in a unique position to shape the future of car insurance

The core success of the company is built on our existing foundation: There’s a huge market opportunity, and I believe Metromile is fundamentally changing the game. 

I believe in Metromile and the experience the product delivers to drivers. I had a great experience when I had a rock in my windshield and had the claim solved simply. I think it starts first by convincing people with savings on auto insurance. Then, they can try pay-per-mile auto insurance, realize the benefits, and see that it’s a better experience if you ever have a claim.

And I think that’s what makes Metromile so compelling.

What opportunities do you see ahead for Metromile?

I’m naturally a problem-solver, and I can’t imagine a more relevant technical problem than what Metromile is trying to solve. Insurance is probably one of the most exciting data science problems, especially as the future of driving changes. For example, I can choose to drive the car myself or let the car drive. Few companies are positioned to price this dynamic fairly, understand the variable risk of who’s actually driving, and respond to the technical challenges because this dynamic is entirely new. 

I believe in how Metromile plans to approach the problem. We have so much opportunity ahead: We will expand nationwide and start to accelerate meaningfully, and invest for the long-term. We have the resources to scale and build differentiated auto insurance. We can also capture demand as Metromile becomes more relevant as mobility evolves to people’s new work schedules and changing driving habits.

We’re in the early innings, and the people who have the richest data and the best technical experience will win. I joined because I believe we have the team to make that a reality, and I am thrilled to be a part of this incredible company and team.

How else do you spend your time outside of work?

I’m a lifelong Seattle sports fan and follow football closely. I’m a big Seahawks fan. Growing up in Seattle, I became a Washington Huskies fan as well. I also just picked up being an assistant tee-ball coach for my 6-year-old. And we just got back from a weeklong trip to Kauai; it made me remember how much we love to travel as a family. I can’t wait for all of us to get out there again to explore and see friends and family.

Speed round:

Are you a better driver or passenger?

Driver for sure. I like to pick the speed and the route.

What are you listening to in the car these days?

Harry Potter and the Goblet of Fire on Audible with the kids (though I’m a fan, too) and 90s hip-hop.

Favorite road trip?

I’ve driven many times between Seattle and San Diego, and there is so much to see. It’s so beautiful, and there are so many fun places to explore along the way. I enjoy the mountains and beaches and walking around the cities in between.