How I Built My Career: Developing Products Through Innovation and Collaboration

We’re hiring! Hear from Brandon about the keys to success as a product manager at Metromile and what it’s like to be at the center of innovation at an insurance company.

Career growth at other companies can be like one-way streets: there’s a clear line of sight that gets you to where you want to go, but there isn’t much room for venturing out or trying new things. 

At Metromile, we like to do things a little differently. All of the left turns, byways, and side streets are not only fair game but encouraged. We make it a point to provide Metromilers with a breadth of exposure and exploration to help guide them along their career journey, whether taking professional training courses to move up into a managerial role or hopping on over to an entirely different department. 

Get an under-the-hood look at what life is like at Metromile from a member of our product team.

Brandon, Metromiler since October 2017

Director, Product Management

We’re hiring! Hear from Brandon about the keys to success as a product manager at Metromile and what it’s like to be at the center of innovation at an insurance company.

What brought you to Metromile?

I was drawn to Metromile because auto insurance hasn’t changed significantly in such a long time — super nerdy, I know! At my previous company, I briefly worked with one of the large national insurance companies. It was then that I realized how stale the industry was and that there is a lot of room for innovation. Being in the San Francisco Bay Area, I heard about what Metromile was doing and decided to make the change.

Being right in the middle of all of the action, what do you think has helped make Metromile successful?

Being able to work closely with so many different teams, whether it’s user research or marketing, helps us develop a very well-rounded product offering. We can have open conversations and challenge what hasn’t been done or what could be done better; we’re not afraid to ask, disagree, or share new ideas. You can chat with the CEO, a vice president, whoever. If you have an idea, it’s on the table. It doesn’t feel like it’s this big, stuffy pitch. 

Our level of collaboration has been incredible. I love working with the executives without all of the bureaucracy and red tape you might experience at a bigger company. That’s not our culture; we do things differently, and it plays to our advantage. In my opinion, freedom and transparency are required in the highly-regulated industry we find ourselves in. Intuitively, you might think it would be the opposite, but having worked with members of the departments of insurance in the states we’re available in, it’s clear that we’re all aligned on building a fair and equitable product for drivers. And they’re open to our methods of innovation!

What Metromile products have you helped develop?

When I started here, my first role was to help launch Metromile in Arizona. It was a hit-the-ground-running kind of project and proved to be a great way to learn about the industry right off the bat. Being involved in a state launch helped open up doors into diversity, different rating factors to consider, and behavioral pricing work. After about a year, I was able to work closely with Dan, our CEO, and with our data science team more. I think a big part of our success comes from working with such a wide variety of people from all professional backgrounds. 

Eventually, I moved into a principal product role, which came with a lot of very interesting, hands-on work of overseeing our product’s actual implementation. After talking with my manager, I realized I also had the opportunity to manage more junior employees on the product team, which has always been an interest of mine. Having those direct, open conversations with managers is a true reflection of our culture, especially with transparency being one of our core values. So that was my next phase, continuing to build out products and mentoring others to further develop the product team.

What is one of your favorite aspects of life at Metromile?

Especially with the teams working from home during COVID-19, I always have felt like I have a great work-life balance; I can take a break when I need to or dial into a meeting while I’m on a walk. The level of autonomy we have was one of the things that brought me to Metromile in the first place and has been a big reason for my happiness here these past few years. 

Autonomy is also how we’re all able to dabble in and explore different areas of the business. For instance, I could never see myself being a full-fledged data scientist, but understanding what goes into that line of work and how that team builds predictive models from scratch is super interesting to me. To this day, I am still learning more about it, and ultimately, it helps inform my work on the product.

What do you love the most about your work?

We have the creative, collective mindset of a technology company. We’re constantly moving, working, and evolving. You’re not going to work on developing a single-function button for five years. 

We operate at a pace that inherently brings a different kind of experience where you can be involved firsthand on strategies and work on a lot of projects within a single year. That’s always been a huge draw for me, personally, to see how everyone else thinks and how they approach these broader solutions of how to make pay-per-mile insurance so simple that people get excited about it. Auto insurance is boring for most people, but we’re doing something different. 

Every day I’m learning new things about the industry — and, at this point, I know way too many insurance acronyms — but it all helps inform how we can package our product and what makes the most sense for our users. I love that constant challenge. 

What are you most excited to develop in 2021?

I can’t wait to start rolling out into new states and get into that process again. It’s always so exciting to develop a game plan when we introduce pay-per-mile to an entirely new market because there are so many audiences in each state. “Low-mileage drivers” don’t all look the same. 

It’ll be great to get into that momentum of growth and adding to our community of customers. We’ll get their fresh feedback, which will help us shape the product even more. Every person in the company is involved and has a major part to play. 

What advice do you have for Metromile candidates who may not come from an insurance background?

I always try to assure candidates not to be intimidated by or focus on having an insurance background; I had only a sliver of exposure to the insurance industry prior to joining Metromile, but it never hindered my work here. 

From the start, my team and the projects I was working on helped me learn and get up to speed very quickly. So many Metromilers come from an array of industries, and it only helps strengthen our business perspective. 

I also wouldn’t want anyone to be scared of auto insurance. Yes, it’s a highly-regulated industry, but  I’ve noticed repeatedly that we continuously challenge the status quo. It’s ingrained in the culture we have. We assess how we go about things, how we can change things up in the name of efficiency and improvement, whether it’s a sales call script or how we develop our road maps. There’s a huge appeal to be a part of a company in an industry that’s rapidly changing. It appeals to those looking to not only grow in their career, but who also want what they do to have a real impact and know that they’re helping modernize a once traditional sector.

We’re a technology company that does insurance. I think that helps people understand our differentiation from these other larger insurance incumbents. Everyone’s heading in the same direction. Having that focus on creating an incredibly simple product that people love aligns Metromilers as a whole, no matter their background.

Interested in joining the Metromile team? Check out all of our open positions. We can’t wait to hear from you!

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Demi Greco has also been on the career jungle gym at Metromile. She is a communications specialist by way of a receptionist turned executive assistant.