Blog » Life at Metromile

Metromile aims to put people first. We’re focused on using data science, customer-centric design, and the latest technology to reimagine insurance and make it more affordable, equitable, and flexible.

Our data scientists, engineers, and technologists are obsessed with savings, service, and features that drivers will actually want to use — not buzzwords like disruption, innovation, or other “techie” branding.

For Khalal Walker, a senior software engineer, the realization he didn’t like coding all that much had a big impact on the start of his career. Khalal said he was halfway through his degree program at Jackson State University when the realization struck.

“I thought, ‘I’m going to find a job that has nothing to do with coding.’ I got my first role out of college as a software QA tester, testing code that developers wrote to make sure it matches requirements,” Khalal said. “After a few years of that, I didn’t feel challenged in the role. It was government work, and the iterations were a lot slower. I started looking somewhere else because I wanted to be on a team that was more agile, moved faster, and I came across Metromile.” 

That desire for a challenge was met in his role as a front-end engineer in Metromile’s quote and enroll platform. Anyone who’s seen a Metromile ad or found their way to getting an insurance quote has interacted with that platform. Khalal’s role is to make it easier to become a member of the Metromile community. He develops and tests changes to the platform to see how they impact the user experience and optimize the experience. 

“People say first impressions are everything, and this is the piece of software seen by pretty much everyone who has a policy with Metromile or even just checked us out. They’ve all touched this software,” Khalal said. “I think we play a big role in things… at larger companies, people don’t always feel like they’re affecting the bottom line of the company. But everyone sees this code; it’s very impactful. To have that amount of visibility within a company and outside it, it’s cool.”

But a career is made up of more than the tasks and projects that take up a day’s work. At Metromile, it’s the culture and the people who are just as important as the product and software itself.

“There are a lot of bright people at Metromile, and they’re so willing to answer questions, to share information,” Khalal said. “It’s probably one of the biggest things I enjoy, that work culture that encourages asking questions and gaining more information. Some companies are really competitive, where questions are seen as weak, or you’ll be passed over for promotion if you don’t know some piece of information.”

It was the company culture that brought Khalal back to Metromile recently. 

When a friend joined a startup that helps make it easier to donate stocks to nonprofits, Khalal saw it as his chance to “do some societal good.” But after three months, he knew it wasn’t the right fit.

“When I was contemplating leaving, I wasn’t applying anywhere else; I just wanted to go back to Metromile,” he said. “When you go to a smaller startup, funding, benefits, the people you work with, the working hours, they’re different.”

Khalal wanted the “different” he’d experienced at Metromile.

“All of us on the front-end team have a meeting every Friday that’s just 30 minutes, but it’s not about work; we just catch up. It’s a virtual happy hour; we just chat about life, how things are going,” he said. “I think those things are really important because we’re not robots, where the only conversations that we have are work-related. We’re still people. A company is made up of people first.”

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We’re building a community of drivers who come to Metromile for the savings and stay for the experience. Our diverse team combines the best of Silicon Valley technologists with veterans from Fortune 500 insurers and financial services giants focused on using technology to reinvent insurance as a tool for financial resiliency.

Check out open positions at Metromile or give our pay-per-mile auto insurance a try by taking a free Ride Along™ trial from the Metromile app.

To celebrate Asian American and Pacific Islander Heritage Month, we’re featuring our incredibly talented AAPI-identifying Metromilers. AAPI Heritage month is a time to reflect, celebrate and recognize the incredible influence of Asian Americans and Pacific Islander Americans in our history, culture and achievements. At Metromile, we celebrate our Asian American and Pacific Islander employees and the role they play not just in our organization, but in the world. 

We’re excited to spotlight Junna Ro, General Counsel at Metromile. 

Q: Can you tell us a little bit about yourself?

A: I was born and raised in San Francisco, and am of Korean descent. I went to UCLA for college and Santa Clara University for law school. I have been practicing law for 24 years and feel blessed to have such an exciting, challenging role here where I am continuously learning, growing, and contributing.

Q: What’s your role at Metromile?

A: I lead the legal team, and see my role as an advisor on legal, regulatory, and compliance matters, helping our partners effectively navigate risk to advance our business goals.

Q: Can you tell us what Asian American and Pacific Islander Heritage Month means to you? 

A: This is a month to reflect on the AAPI contributions to the community, celebrate our heritage, and raise awareness around issues of importance to the AAPI community. This past year we have witnessed an alarming rise in hate crime against the Asian community, and it has been particularly important for me to speak out against this dangerous development and to encourage action. The recent passage of new Asian hate crime legislation is one major step in the right direction to address this issue. Ultimately, in sharing more about the AAPI community, I am hoping that we learn more about each other and discover that beyond our differences, we also have much in common.

Q. What is your favorite cultural tradition? 

A: As an American of Korean descent, I love being able to cultivate an interest and appreciation for the Korean language, food, and customs with my children, who as teenagers, are evolving in their own self-discovery. My son recently interviewed me for a project in one of his Asian American studies classes at UCLA, and it was such a special experience to share with him my upbringing and the Korean cultural influences that impacted my life as his research subject. My daughter is a kdrama and kpop fan, and it is so wonderful to see her staying connected to her roots in this way.

Q. What do you hope to see for the Asian community in the future?

A: I’d like to see Asians reach parity in representation in all aspects of American society, and particularly in law and politics. For instance, we are not seeing the same representation that we see of Asians in law school as we do at the law firm partner and general counsel ranks. According to a recent report from the Bureau of Labor Statistics, 88 percent of lawyers are white, which makes the legal profession one of the least racially diverse professions in the US. Furthermore, a recent Vault/MCCA study on law firm diversity reveals that even though one in four law firm associates is a person of color, they comprise only 10 percent of equity partners. And while Blacks, Latinos, Asian Americans, and Native Americans now constitute about a third of the population and a fifth of law school graduates, they make up fewer than 7 percent of law firm partners and 9 percent of general counsels of large corporations. Asian American attorneys comprise about 12% of associates but just under 4% of equity partners, and under 4% of the general counsels at Fortune 1000 companies. I’d like to see this change. 

Q: What is one activity or dish that you think everyone should try?

A: I think everyone should try to learn to read Korean! It is actually really easy, and has been deemed one of the most scientific languages ever developed. 

Q: Do you have a role model in your life? If so, who are they and how have they helped you in your journey? 

A: My dad. He has had a longstanding career as an educator and in politics, and is currently retired but pursuing his third career as an artist. He continues to seek out inspiration for his work and to find his unique identity. When I observe his life, I realize that he has always been fully committed to his goals and his passions, and is driven by the desire to have a meaningful impact on those around him. I share the same convictions and continue to be inspired by his example. 

Check back soon to meet more Metromilers. If you’re interested in joining Metromile, check out our open positions at https://www.metromile.com/careers/. 

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 celebrate people from all backgrounds and walks of life and recognize that skills come in all shapes and sizes. It’s your work ethic and initiative that mean the most. We make it a point to provide Metromilers with a breadth of exposure and allow for exploration to help guide them along their career journey, whatever direction it may be. 

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

Dev, Underwriter

Metromiler since August 2018

What was your career like before Metromile?

I don’t have a formal degree in any area and have worked in a few different industries, from call centers to manufacturing, but nothing insurance or tech-related. I was still figuring out what I wanted to do. A friend of mine worked at Metromile and always talked about how much he enjoyed the culture and how everyone was so friendly. It seemed like a unique work experience, so I decided to check it out.

During the interview process, I found that not having a degree wasn’t a hindrance at all. The hiring managers were more focused on my relevant work experience and what I could bring to the table, and I was happy that I was seen for my skills and work ethic. It felt like a level playing field.

What has your career at Metromile been like?

I started as a customer experience agent on the phones, helping our drivers with their policies. From there, I was able to move directly into our underwriting department as an underwriting assistant. Now, I am a bit more behind the scenes, reviewing policies when an issue arises or making the necessary adjustments when adding coverage to another vehicle. 

There are so many factors that influence car insurance rates. There are so many vehicle modifications that can be done, so it’s always interesting to see what I’ll come across on any given day. Once I worked on rating an old decommissioned ambulance that someone was using as their personal vehicle!

What do you like most about working at Metromile?

The opportunity, one hundred percent. As a young twenty-something, I’m proud to have gotten so far in my career already, especially not having a degree. And I also love my team and everyone that I’ve met at Metromile. It makes such a difference in your day-to-day. I don’t think I could find another team that I love so much. You can’t replace that.

What do you see next down the road for you?

I’m hoping to be able to step into a leadership position as we continue to grow. Underwriters at Metromile can soon expand what they manage. As a part of that, I’d like to develop my leadership skills and get my Chartered Property Casualty Underwriter license. It’s a pretty extensive two-year certification that demonstrates a high level of expertise and decision-making in underwriting. 

What’s been the biggest thing that’s helped you further your career at Metromile?

I ask all the questions all the time. It helped me because I’ve run into a lot of odd scenarios in my work, so don’t hesitate to get another person’s opinion; get as much knowledge as you can. 

Also be curious about other departments because you might not realize right away where your interests lie. Once I shadowed one of our claims representatives to learn more about their role and responsibilities. They loved it! No one’s ever going to turn you down. Even if  you realize it may not be something that you would necessarily move into, just having that exposure into the business is so helpful. There’s so many facets within insurance and Metromile that I never knew. And I never would have known unless I asked around!

What advice would you give a Metromile candidate who may not have a formal degree or may not come from an insurance background?

It’s not something to be put off by or intimidated by. Our team truly cares to invest in talented people. A piece of paper from a university isn’t the end-all, be-all. Go for it, and apply! 

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

Experience the power of pay-per-mile and see how much you could save on car insurance by taking a Ride Along™. 

Get your free quote in minutes, or earn rewards when you refer your friends and family.

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

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!

Experience the power of pay-per-mile and see how much you could save on car insurance by taking a Ride Along™. 

Get your free quote in minutes, or earn rewards when you refer your friends and family.

At Metromile, we like to do things a little differently. (We are disrupting the auto insurance industry after all.) From offering drivers more fair and personalized pricing to streamlining claims with our AI-powered process, innovation is at the core of everything we do. 

Especially when it comes to our employees’ development.

Gone are the days of traditional career paths. It’s all about the career jungle gym now, and with how competitive job hunting is these days, it can feel like a free for all on the job-market playground! 

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, 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 providing access to training courses to help move up in your current role or into a managerial role or hopping on over to an entirely different department. 

In this blog series, you’ll hear from some of our very own to get a taste of what’s possible with a career at Metromile.

Devin, Fulfillment Administrator

Metromiler since March 2019

What brought you to Metromile?

At the time, I was working at a consulting firm and didn’t enjoy the environment. It was a very competitive atmosphere where it felt like I had to fight my coworkers to secure clients. That was the means of growth and success. I attended a Metromile holiday party as a plus-one, and just from that one event, I felt like I fit in with the people — not just interest-wise, but I got the sense that everyone had this collaborative goal in mind when it came to their work. I felt, they wanted to help each other succeed. That was the turning point for me, and I applied to Metromile not long after that.

What’s your career jungle gym looked like?

I came in as a customer experience advocate. I went through the training, and Metromile helped get me licensed as an insurance agent — the whole shebang. At the time, the customer support team was much smaller than it is now, so we had to be very scrappy, and I learned very quickly. 

A few months later, my manager let me know there was a role being developed for someone to work with our finance team and supply chain manager for all things related to our Pulse device operations. I had been interested in that area of the business and had even started teaching myself some of those skills with the help of a couple of the analysts on our finance team. I got the role, and I’ve been in this fulfillment administrative role for over a year now.

How has it been expanding into this new territory?

It’s kind of rare to have somebody like me, with formal project management experience, switch to customer service. But that’s exactly what was needed for this position. I believe in our mission and love this company so much that I was willing to go out of my comfort zone to take on this new role and its responsibilities. I started doing some guided applied learning through a tool called Data Camp. And it’s not just the abstract learning — it’s a broad skill that I’m starting to get down, which has been really fun. Now I’m able to work on applied projects with it. I still come up against things where I have to seek help and answers from others but I have such a great network of coworkers. I feel like I’m doing something impactful for the company. 

At my previous company, no one cared as long as you did your job and what was asked of you. Here, I feel Metromile genuinely wants to help every employee realize their interests in order to take their career to the next level. I’ve had the freedom to craft my role based on my unique skills and passions, which I really appreciate. It’s one of my favorite things about being at Metromile. 

I really enjoy working on cross-functional projects with so many more people outside of my immediate circle, especially coming from the customer service field. On the flip side, I’ve really enjoyed being a resource or a point of knowledge to my colleagues. Metromile is technically larger than my previous company, but I feel like I have a greater impact here. 

What do you have coming up that you’re most excited about?

One of the things I think is so cool about Metromile is that we’re so data-driven, and I’ve wanted to learn more about data analytics. It’s interesting to understand how our customers drive and identify trends in driving habits. There is a big area of opportunity with the analytics available from the Pulse device that I’m excited to explore more of. 

I’ve also recently been bolstering up my work with engineering. Within my everyday work, I will sometimes catch something that could be improved. I’ll bring it to the engineering team, but instead of just taking it off of my hands right there, they’ll keep me in the loop and help me resolve the issue. 

It’s also been really interesting working with finance and seeing the big picture of our company. It helps inform my work and gives me that other perspective so that I have a holistic view of the business. Creating these kinds of cross-department solutions has been so important and helpful to furthering me in my career.

What’s been your favorite part of your Metromile experience?

To this day, I still think the people are the best part of Metromile. It’s been exciting to be a part of such a hands-on, collaborative culture and see the company grow. It’s so rare to find a workplace now where you can mesh with and you can truly feel like you can be yourself with; that was something I had never really had before Metromile. 

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

If you believe in what this company does and you’re willing to put in the work, just go for it. I don’t have any formal technical or finance background, yet here I am!

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

Experience the power of pay-per-mile auto insurance and see how much you could save by taking a Ride Along™. 

Get your free quote in minutes, or earn rewards when you refer your friends and family.

Meet Sana Farrukh, software engineer extraordinaire and a member of our mighty Boston team. (Aside: the team is looking to grow!) Here Sana shares about her background, what drew her to Metromile, and why she likes holding down our fort on the east coast.

Tell us a little bit about your background.

I am originally from Lahore, Pakistan. Back in 2015, I came to Boston for grad school and graduated from Tufts. My area of expertise is in computer networks, more specifically internal data center networks.

What interested you about Metromile?

There were a few things that compelled me to explore and advance my career with Metromile:

1. The vast variety of interesting projects that Metromile offered based on the collected telematics data really spiked my interest. This is still a relatively new field, so there still is plenty of opportunity to explore even more interesting projects.
2. It offered an entirely different domain, compared to what I had experience with, in academia. So I wanted to move into something different.
3. As a small company with new, budding projects, Metromile offers the opportunity to work on projects from start to launch, not to be pigeon holed on one product or discipline. That means, too, that all my contributions are meaningful. 

 And now that I am here, it is also the people I work with and the amazing teams I’m part of, that makes me want to come in everyday.

As a software engineer, where specifically is your work focused right now?

So far I have been lucky enough to work on a few different projects: customer outreach, our analysis of driving behavior, mobile telematics integration (that is, syncing customers’ phones with their driving data). At present, my work is focused on making the new customer experience the very best possible one. This means ensuring that the customer receives consistent and coherent communication from us in their first few weeks and that their experience with the Pulse device is seamless.

Boston is a smaller office than our San Francisco and Tempe locations. Plusses and minuses?

Boston is indeed a small team, which is one of the things I love about our office. 

It is relatively quiet, which works best for me as I like to work in quiet environments. And being three hours ahead of San Francisco, we start early and get adequate time to work continuously before afternoon meetings start. 

Being a small team, everyone knows everyone. We often find ourselves taking a deeper dive into discussions about current teams, projects, interests both within and outside of work, vacation plans, pets, etc. Impromptu lunches often gather the whole office on one table — you can’t do that in a big office.

With everyone sitting close to everyone else, it is often effortless to seek guidance and help on tasks we need a second opinion on. Despite our size, we still have a good mix of folks from different teams, so we’re able to apply diverse expertise to problems.

What kind of person would you suggest consider working at Metromile?

Metromile is more than just an insurance company. It offers a unique combination of IoT, engineering, research, and, yes, insurance. Anyone who is interested in the intersection of those things should definitely look into Metromile.

As Metromile’s Quality and Compliance Manager, Prentis Ginn wears a bunch of hats. The San Francisco Bay Area native holds a diverse set of responsibilities: liaising with regulators, implementing user feedback, and ensuring Metromile’s team members are delivering the best service possible. It’s a busy schedule, which Prentis has worked his way toward over nearly six years at the company, starting as a customer service agent and working his way up through quality assurance before taking on his current role. We asked him to offer a bit of insight into his world, both in and out of the office.

Tell us a little bit about your background.

I’m originally from the San Francisco Peninsula. I went to Chapman University in southern California and after graduating, I moved to New York City and worked for a fashion and design startup. Then I moved back to San Francisco to work for Metromile. 

What initially drew you to Metromile?

Every startup likes to say they’re “disrupting an industry.” Metromile was the first company I interviewed with where I actually believed that. I think I met with around ten people during my interview. Best decision I ever made. I immediately fell in love with my team.

How has your role evolved over your time there. 

Being here for almost six years, my role has definitely evolved over time. I was initially brought in to build out our customer experience team. That morphed into quality assurance and looking out for our CSAT and NPS (two core customer service metrics). Now, as a member of our Legal and Compliance team, I coordinate our regulator inquiries and administer our contract management system, and regulatory and compliance platform. 

What do you think makes Metromile so special?

It’s a unique business model. And the career opportunity is special — I’ve gotten to take on a number of different roles here that I might not have elsewhere.

Your first job at Metromile was Sr. Customer Experience Advocate, which involves talking to customers every day. How has this influenced your career path?

Having the ability to quickly process information, strong communication skills, and a genuinely empathetic mindset — these are qualities I’ve taken with me to other roles. This passion has enabled me to empathize with our customer’s position and think outside of regulatory requirements when communicating with various Departments of Insurance.

To those in customer-facing roles, my advice is: you know more about our customers than anyone else. If you see opportunities for improvement, speak up! You are the subject matter experts.

What do you do for fun when you’re not working?

I’m an exotic cat breeder…

Just kidding. 

However, I do have an exotic breed of cat called a Toyger. Other than that, I play Madden a lot. I play flag football on Saturdays with friends, I’m in five fantasy football leagues…I guess you can say I really like anything football-related. I’m a social butterfly, I’m always out and about on the weekends and I love carbs, sugar, and gluten.

Originally hailing from Washington State, Shannon Wright swapped the rainy Pacific Northwest for warmer temps in Arizona, unsure of her true calling, but enthusiastic to enter the working world. “I originally wanted to do broadcast journalism and then ended up with a public relations degree, but really had no idea what I wanted to do,” she says. “One of my good friends was a recruiter at a review company in Arizona and said I’d be great in sales. I really loved it!”

While Shannon had discovered a professional strength, after a few years in the position, she began to get curious about other opportunities at a new company making waves in the car insurance industry. “One of my really close friends was a manager in customer service at Metromile,” she says. “We’d be hanging out at girls’ nights and she’d just be raving about how much she loved her job. I was so jealous!” Wright liked going to work, but she began to wonder if she could ever really, truly love it. In her current role as Metromile’s sales manager, she definitely does.

“I volunteered to work a half day on the Fourth of July and some of my friends said, ‘oh no, that sucks,’ and I’m like ‘no, it’s okay, I’m excited to be with my team!’”

Here’s more about how this former sales wiz found her dream job. 

What was it like transitioning from your previous job into your first role at Metromile? They seem similar in the sense that both involve a lot of connecting with people. 

I had phone experience, but it was very different because I was now on the customer service side as opposed to sales. It was like starting over at square one as an entry level customer service agent, so that was a shock. I ended up being at Metromile for almost exactly a year before I was promoted to train all of our new sales hires, then our service hires — and I’ve even dabbled in claims training. I’ve joked that every four to 12 months, I do a different role here.

How many people did you train at a time?

Anywhere from four to 10 new hires in each class, but it really depends. The training is a month-long program so I was really going back to back for about a year before I switched into management. 

And how did that switch come about?

My current boss approached me about management and said he thought I’d be a great fit. I loved training, don’t get me wrong, but I wanted to try it out and he encouraged me. So I was an agent for a year, then in training for a year, then I switched into customer service management, and I was in that role for seven months before I switched into sales management. So it’s really come full circle — I can’t get enough of sales!  

What is a typical day like for you?

A typical day starts with coming in — that’s step one! — and then running a daily huddle with my team to get them super excited for the day, setting goals, and then just being there as a resource. I’ve known both sides of the business in customer service and sales, and here at Metromile, we do a lot of shadowing and coaching in the moment, so I’ll put on my headset and randomly listen to representatives’ calls live as they’re happening. I sit on the floor in the middle of the whole team so I’m there for coaching, and of course I have the typical one-on-ones with the agents once a week. Then there are also other team meetings. It’s really about me being a resource.

How would someone know if Metromile is a potential good fit for them?

Typically, if they’re driving less than 7,500 miles a year, we save them money, so that would be our major selling point. Metromile is really for low-mileage drivers — we can save them money because they’re not on the road much, so they’re not as much of a risk. That’s what keeps our prices down.

Why is Metromile such an awesome place to work?

There are so many advantages to working here. If I worked at a more rigid, non-start-up type of company, I never would have gotten promoted in my first year. Metromile is really good at developing employees as well as finding focus areas and things employees are good at to make those internal promotions, and I think that’s great.

It sounds cheesy, but I love our culture and this company. Whenever I talk to anyone, I’m now similar to the friend who brought me on board — I rave about how much I love Metromile!

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Want to join Shannon and the rest of the team? We’re hiring in Arizona, San Francisco, and Boston.

When potential Metromile hires meet Jenn Hall, they’re likely not surprised to learn the six-foot-two director of talent acquisition used to play basketball. What they may not know is how her 15-year career on the court influenced her professional life today. “Basketball was all I knew — I was recruited into recruiting,” she says. “They told me tech recruiting was the hardest kind, so I said, ‘sign me up!’ I wound up applying the same fundamental methods that I used to become a D-1 basketball player: practice, commitment, and discipline.”

But the grit and determination Jenn developed as an athlete shaped her personal life as well. After graduating from Vanderbilt University, the Orange County native felt liberated to start embracing her authentic style — and her sexual orientation. “I came out at 23 and just wanted to feel comfortable in my own skin,” she says. “I had to figure out a lot, do a lot of self-discovery, and become more self-aware. It was challenging — when I stopped playing sports, I didn’t have distractions to cover up the other things in my life. Sports had always been my number one priority, so I had to figure out what motivates and inspires me — and I had to stop paying attention to what people were saying.”

It turns out that what inspired Jenn and continues to get her fired up to go to work each and every day is the opportunity to help others uncover their own unique strengths. “Staying strong wasn’t always easy, but It’s all about finding your voice.” We talked with Jenn to learn more about the ways discovering her identity helped contribute to her success and happiness.

How did you get your start in basketball?

I found my love for basketball when I was seven years-old, and that was really my first career. I played for 15 years. I started playing travel basketball when I was 12, and played through college — I was Division-1 at Vanderbilt. I could’ve gone to a lot of other schools but wanted to play in the best conference, the Southeastern conference, and get a degree. I chose a degree, known as Human and Organizational Development — this provided me the ability to pick and choose curriculum I was interested in, and could apply in the real world after school (Psychology, Communications, Organizational Structure & Processes).

Why did you pursue tech recruiting rather than a professional basketball career?

I had a lot of injuries — I had a broken bone in my foot, neck and problems, bad knees. I knew my shelf life would be super short. I also had a lot of friends in the WNBA who weren’t making money and were living at home and I didn’t have that option at the time.

You came out during that transition from sports to recruiting, right after college — tell us more about that time in your life.

It was hard. Really hard. I grew up in a conservative Christian household and it was not accepted. I had always been in a really good place with my parents and had talked to my mom like five times a day…and then didn’t talk to them for five years. It took a lot of patience and time. Basketball was my distraction and I was used to having to prove people wrong, so that was the mindset I had. I had supporters around me who made me feel like it was okay for me to be myself, like my best friend since seventh grade, Christina — I ended up recruiting her!

When did your family come around to your decision to embrace your true identity?

It was at my brother’s wedding seven years ago. It wasn’t easy and there were a lot of conversations. I was 23 years-old and couldn’t do it anymore. I very much hate lying and not being honest. But my family and I rebuilt our relationships and now we’re stronger than ever.

After college, you worked at Google, Hulu, Westfield, and OneMarket — how did you eventually find your way to Metromile?

I was laid off at my last job and realized it was really important to me to be surrounded by a team of people who truly cared about me.  People might think it’s super easy to find a job in my industry, but the hard part is that there aren’t a lot of companies I’d be proud to wear a hoodie for. It’s like being a basketball player and wearing a team jersey with a number on it; a lot of opportunities weren’t right for me. So I looked on Glassdoor and that’s when I applied to Metromile. I saw so many positive reviews of the leadership team, and even though I didn’t really know a lot about insurance, I saw that our CEO, Dan, is really into A.I. and data science, and I love tech — I’ve always loved tech. So I thought, ‘I’ll just apply, what’s the worst that could happen, they say no?’

But they didn’t! You got the job last August. Tell us about your role.

Right now I manage six people and I have one open role so I’ll have seven people in the next couple of months. I’m a career coach and manage executive recruiting, and as head of recruiting, my team does everything related to attracting, engaging, and hiring the talent we need to be successful as a company.  

How has your personal journey influenced your ability to manage employees and help people find their professional calling?

Being more self-aware has made me more aware of other people, which in turn lets me identify what they’re passionate about and what motivates them. I love being able to sit down and have conversations, sharing what I’ve done, and learning what inspires them. I can see where people can go and I like helping them get there.

You said the Panic! at the Disco song, “High Hopes,” reminds you of how embracing your identity paved the way for your success. Tell us more.

How doesn’t it? It’s like my anthem! The words are very poignant and relate to some situations I had to endure Like, “didn’t have a dime but I always had a vision.” I haven’t had anyone supporting me since I graduated from college and I had to get creative. I was selling my Jordan shoes on eBay to pay rent! It took time to get there. It hasn’t always been rosy and peachy, I’ve worked really hard. And when he sings, “mama said…” that to me is reminiscent of earlier parts of my career that were building blocks, not only to me as a person, but as a leader, and those situations made me even stronger than I ever could have been otherwise. As I went through my journey, I’ve been able to learn how to adapt and I’ve never stopped believing in myself and my abilities. As long as you have that, you can achieve anything.

Our recruiting team is hiring! Take a look at our open roles.

Jenn is the former Director of Talent Acquisition at Metromile

Here at Metromile, we are all about making car insurance more fair and less painful — some may call this a lofty goal. We know that all it takes to make auto insurance simple and seamless is a bit of data, some science, a lot of technology, and a dash of magic. From the outside looking in, revolutionizing the auto insurance industry may seem easy, but take a peek under our insurance hood, and you’ll quickly realize that it takes a lot of systemization to keep this engine running. And at a company whose whole mission is to reinvent ways to manage risk, it should come as no surprise that our Data Science team is constantly buzzing; building and testing new models and furiously working to analyze Metromile data to find new opportunities to fix how insurance is traditionally “done.”

Revolutionizing an antiquated industry is no easy feat. It takes a village – a village of brilliant humans that are constantly iterating and innovating. One of the best ways to foster a culture of innovation is to work with local University programs like The Master of Science in Data Science (MSDS) Program at the University of San Francisco. It’s a win-win for both us, and the University because it gives students valuable business experience, and it gives us insight into new data patterns, trends, and opportunities.

The Program

The Practicum Program at USF pairs students with bay area companies, allowing them to apply their skills to gain experience, and reconcile mathematical theory with business practice. Each student is expected to create and refine a project with their partner company for 16 hours per week, while concurrently taking classes. This past Winter and Spring, we were lucky enough to have two USF students join us, Chenxi and Fang. They have spent the past six months trying to read mileage from odometer pictures, which can be used to correct the mileage measurements we receive from the Pulse device. This gets to the crux of what makes Metromile different from traditional insurers – we charge for insurance by the mile, so exact mileage is very important, and we are always looking for new ways to track mileage! Chenxi and Fang utilized some deep learning techniques, like the U-net model, in order to deal with object segmentation problems in computer vision.

The Project

During their time at Metromile, Chenxi and Fang applied state of the art techniques to real-world problems and gained experience using deep learning to solve computer vision challenges. Asking Chenxi and Fang what the most challenging part of their project was, they posited that the most taxing aspect was also what they learned the most from, “trying to solve a problem with limited resources and a relatively small dataset. We tried various ways to enlarge the dataset we have, as well as adjust the algorithms we used to overcome the issue.”

When asked whether or not they experienced a breakthrough moment, both Chenxi and Fang concluded. “There were several breakthrough moments during our work on this project, but the process is gradual and requires constant inputs and modification. The biggest challenge of our practicum was the project itself – extracting mileage from the odometer and correctly distinguishing that information from other similar numbers has turned out to be difficult. Luckily, our mentors have been patient and resourceful and have helped us a lot.”

One of these mentors, Chetan Ramaiah – a Data Science Manager here at Metromile – oversaw the internship program and recalled that Metromile had previously hired a 2016 participant of the program. It was the success from previous years that encouraged him to place Metromile in the program again. “The experiments conducted by Chenxi and Fang helped us identify a state of the art solution to a difficult research problem, and the process helped identify the various difficulties in modeling a solution to the problem. In addition, both Chenxi and Fang helped establish a benchmark on the quality of internship candidates.”

Internships at Metromile

According to Chetan, the project was a success.“The project adds a new dimension to Metromile’s mileage tracking abilities. The odometer project can independently verify and improve our mileage tracking from the Pulse and the OBD-II port.” Metromile looks forward to participating in the Practicum in coming years, and plans on taking on more Data Science and Engineer interns next summer. If you are interested in applying for an internship with Metromile please contact David Clifford, Director of Data Science ([email protected]) or Mike Dicarlo, VP of Engineering ([email protected]).