Just outside of Philadelphia born and raised, Jon Coombs spent most of his days on tennis courts competing and grinding out multi set matches, probing opponents’ weaknesses and biding his time before smashing winners. Today, as a Group Product Manager at Flexcar, Jon owns their Risk Product to build an inclusive customer experience and minimize risk costs for this rapidly growing startup.
Jon is an only child but has a lot of sibling-level friends from the suburbs north of Philadelphia. He grew up as a competitive tennis player and still enjoys pretty much every racquet sport, from ping pong to pickleball, and recalls feeling really fortunate that his parents gave him the tools and values needed to build a successful life.
Jon really liked the academic and athletic appeal of the NESCAC schools, visiting five of them on tennis recruiting trips. He formed a good relationship with the tennis coach at Wesleyan, applied early decision, and off he went. He enrolled (and graduated) as a Math & Economics Double Major. Jon had always loved Math but knew he didn’t want to be a pure mathematician. Economics helped provide some business applications to his studies.
When it came time to graduate, he kicked off a pretty broad job search but was looking to land an analytical role. He knew he wanted to be in the Boston area and interviewed across a variety of opportunities in finance, marketing, and insurance before landing at Liberty Mutual. He’d interned there the summer before, so there was familiarity, and they had a great analyst development program where he could rotate through different functions. Jon’s interest in tech came a bit later.
The opportunity to jump into the workforce with a cohort of people his age with similar career interests & drive in one building was a key selling point. And the analytical opportunities to add value inside of a large business were endless.
Jon was looking for a fun, fast paced city atmosphere without it being too massive, and Boston fit that bill. Whether it’s experiencing the seasons around New England or going for a run by the water, Jon and a lot of his friends who settled here think the city has a lot to offer everyone. According to him he’s tried probably every Mediterranean or Italian restaurant in the city by now. I’m skeptical though.
In terms of the tech community, he originally viewed Boston as a biotech hub. With time he’s seen little nests of a ton of different tech companies established out here in the years since. It’s grown into a tight knit “you can find what you’re looking for” type working environment. It helps having elite academic institutions nearby too.
Over his first year out of college, Jon completed quarterly analytics rotations through Product, Marketing, Distributions, and Claims. Jon learned technical skills and how to build business cases and be persuasive. He was taught when to take a 10,000 foot view vs. get into the weeds. He figured out how to align on the amount of detail to bring to various conversations and how to talk to executives vs. peers.
Looking back, Jon estimates he probably interfaced with 1,000 people in meetings, presentations, and various interactions over that first year. Sheryl Sandberg would have been proud of the ways he learned to “bring himself to work” and grow into a respected & productive member of the organization.
After his rotation concluded, Jon joined the Marketing Analytics team. He was put in charge of a project doing competitive analysis of 10-12 peer companies’ marketing strategies. He took the project and ran with it. His work was so thorough and helpful that he got the opportunity to present to Liberty Mutual’s CMO. Through this experience he learned that if you put in the effort and do the job rigorously, good organizations will recognize that work and send it up the chain. Jon learned it’s the quality of your work that will get you noticed.
His work in Marketing covered direct mail, email, and third party marketing analytics. He got to see up close that product building and marketing efforts can sometimes have different goals. He began thinking about how to better align those initiatives and it became a catalyst for him to get closer to building the core offering. He found a role on the underwriting & risk side of the business as a Senior Analyst in Liberty Mutual’s Product org.
This role allowed him to work cross functionally with data science teams building models that put smarter decisioning into the platform. Their team created funnels for various cohorts of the business based on information captured at submission and throughout the customer lifecycle. He got to see the positives and negatives aspects of customer impact around eligibility & overall “productization” of the experience across mobile & web.
He was expected to be the analyst (driving the business case) as well as the Product Manager with a focus on Auto & Home product lines. He worked closely with Engineering, comparing the role in size & scope to a traditional “Amazon-style PM role”. He obtained increasing levels of ownership, impact, and trust to carry things forward, eventually taking on a Director role within the Underwriting Product team.
The biggest project Jon implemented was a complete revamp of how they approached auto insurance eligibility nationwide. It was a complex, bespoke regulatory process by state that effectively split the product initiative into 50 miniature products.
Jon accomplished a lot over those 7 years at Liberty Mutual. And after a time, he felt like he had achieved everything he wanted to achieve at the company. He was ready to build products from the ground up at a smaller technology company.
He laid out his search tactics, which I thought were really helpful to share. First, he did broad research. He was looking at startups between 10 and 500 people. He wanted to be realistic about potential crossover opportunities and bringing relevant experience to a new employer, looking at insurtech, telematics, and mobility companies.
Next, he dove back into networking by connecting with friends and friends of friends through warm introductions. He also did some cold outreach via recruiters, former hiring managers, folks who used to work at Liberty Mutual, etc. Some don’t respond, and that’s ok!
He spoke with startups across the Boston tech landscape about his combined product and analytical background, focusing primarily on industries with crossover strength from his previous experience. Within 1-2 months, his interviews began. Flexcar was an interesting opportunity because they were specifically looking for someone who could help them build products pertaining to customer risk, an area in which he had deep context. He also was lucky enough to discover through his networking that he had a former colleague there who could provide additional company context.
Jon got the job and joined Flexcar as their Group Product Manager for Risk. Flexcar is a tech-driven, vehicle subscription growth stage company based in Boston. He’s helping Flexcar productize customer eligibility and the customer experience around driver quality. Just like he did at Liberty Mutual! He’s helping their team evaluate which rules they should use for driver eligibility and risk mitigation and building that into their product offering. He’s helping the company close the gap for customer communication by building different pathways into their funnel, handling payment risk, dealing with fraud, and making build vs. buy decisions.
Most importantly, he’s helping bring rigorous risk assessment to Flexcar’s slick ecommerce feel, optimizing the customer experience while enabling the company to feel secure in its driver base. Here are the things Jon has learned from his career at insurance leader Liberty Mutual to leading a group of PMs at FlexCar:
Don’t Just Check the Box – “I’ve seen people during my career get a task, do it, and check the box. What served me well earlier in my career was ‘here’s this general analysis’ and I would take it, run with it, and turn it into something bigger than the initial ask. That can be impactful because then you create opportunities for visibility”. Showing yourself as someone who can deliver a project, product, or result creates more opportunities for you to have more ownership.
Strengths Create Opportunity – “Don’t feel like you have to decide your path right away and continue down that path. You can always sell your strengths as you build them and people will acknowledge those if they are genuine. Don’t be afraid to pivot a little bit and put yourself out there”
Communication – “Always follow up with people and close the loop on things. There’s always a lot of work that becomes open ended. Someone might bring something up in a meeting but it can just disappear. One thing I’ve prided myself on is to not take for granted when someone says ‘ this would be really interesting or good to have’. That person may not remember but they will certainly remember if you follow up and provide that feedback after the fact.” Following up and letting people know you heard them is really impactful
Jon’s excited that he’s been able to find a role he wants to be in for a long time, serving as a product management leader. Eventually he’d like to grow into a GM, managing PMs & operational teams, all while fine-tuning his people management skills. He’s looking to continue to grow and contribute to product strategy, helping to more expertly steer the ship.
If you’d like to get in touch with Jon you can find him on LinkedIn, designing better customer experiences for Flexcar, or on some type of court in the Boston area. Thanks for sharing Jon. We’ll be watching Flexcar’s growth and be reminded of a better way every time that check engine light comes on. Best of luck in the years ahead!