What's it like to work in Product at Clearcover?

By Kirill Polevoy  4 minute read

By Kirill Polevoy

4 minute read

Hi, I’m Kirill. I’m a Senior Technical Product Manager at Clearcover, a VC-funded insurtech that’s helping people pay less for smarter, better car insurance coverage. 

Here’s what it’s like to work on product at one of the fastest-growing tech startups in Chicago. 

  1. We’re serious about solving problems.

We don’t play it easy. We’re an up-and-coming company claiming a piece of a market which is dominated by companies that are much larger than we are. That means that each day looks a little different and that, ultimately, my job is to get creative and solve a lot of problems quickly. 

The way I do that changes each day. As the product lead on the acquisition team, I’m responsible for making sure the team works on the right problems in the right order and we understand the issues we’re addressing. It’s easy to get so caught up  fighting small fires that you don’t face the deeper issue that’s actually hindering your progress. So, at the beginning of every day, I sit down and take a hard look at daily goals to make sure they align with the team’s Big 3 Goals for the week. If it looks like we’re losing focus, I have the conversations necessary to make sure we stay on track. 

Because of our size and our laser-focus on finding solutions, Clearcover is incredibly agile. We iterate on the fly. If a meeting shifts in a direction  that doesn’t require everyone who was on the calendar invite, we tell people to go. We do our best to over-communicate, practice candor, and to talk about what’s not working. Essentially, if something isn’t working we change it, and every member of the team has a voice in finding the solution. In a company that’s growing so quickly, every decision has a measurable effect on company growth. It’s certainly a challenge but it’s also fun.

Also, it might seem obvious, but sometimes my job is simply to make things happen. For example, one of my first projects at Clearcover was figuring out how to validate street addresses. After doing the research, the team decided that purchasing a third-party service would solve the issue. Then I was astonished to learn that I could make the purchase and close the task that day. I didn’t have to fill out any forms or justify my decision to anyone, and I left work with a major challenge resolved.

You don’t get that kind of freedom everywhere.

2. We grow every day.

Clearcover is in two states now and our goal is to be in all fifty. Since we’re actively expanding, my role involves figuring out how our product will look and act in each new market. Since insurance regulations are different in each state, that means no two expansion projects are alike. Before I do anything, I have to figure out the key questions: What do customers need in this state? Where does our product need to change? How can our partners work with us in a way that makes sense for this state? How can we adapt the product to work in this new market without diminishing our core competencies? What does my team not know? What do I not know?  

To state the obvious, my job is never boring.

Clearcover itself is constantly changing, too. One of our fundamental values is to challenge all assumptions, so we’re always rethinking how we do things, questioning first principles, and setting unreasonable goals. We’re not afraid to pivot if it’s the right thing for our company and for the people we serve. 

An example: after going in the direction of being “technology-first” for over a year, we realized that we were limiting ourselves by ignoring one of the best insurance shopping moments for consumers—independent insurance agents. These are people that our potential customers already know and trust. Why would we intentionally avoid a channel that many people prefer? Integrating independent agents would be a big opportunity to leverage our problem-solving skills and technology. 

So now, we’re building a way to include independent agents into our acquisition strategy. With that decision, our product must change. I help figure out exactly how.

It’s an understatement to say that I’ve been stretched by this work and I’m excited to keep learning. The process is never perfect but it is always rewarding.

3. We make space to think about the big picture.

Clearcover is a startup. Things get crazy. But there’s a real respect here for the fact that the best work comes from good thinking. I try to spend time every afternoon strategizing, looking through our backlog of tasks, and adjusting the roadmap to make sure we’re not missing the big picture. Often, I try to set aside time to simply think for an hour. That thinking time is respected because that time is when the ideas which propel our company can emerge.

We also recently instituted “no-meeting Wednesdays” to ensure that everyone has the dedicated time they need to get in the flow and to think hard about what they’re doing. On the other days of the week, I encourage my team to turn off Slack when necessary, to mute email notifications, and to decline meetings if they aren’t necessary. In the end, we’re here to do great work, and the team at Clearcover understands that the process looks different for every person. 

      4. We like each other.

At the end of the day, I work at Clearcover because of the people. In any given week, I have the opportunity to work with engineers, marketing specialists, junior designers, and senior leadership. Kyle, our CEO, has office hours every week, when anyone can go in and have a conversation. We see our company culture as akin to that of a professional sports team—we all play to our strengths while caring about each other a whole lot. We check up on each other, depend on each other, and everything we do is a combined effort. At Clearcover, we’re not simply sets of skills—we’re people. 

There’s also a lot of support for our real lives outside of the office. In my off-hours, I’m a street photographer and occasionally have gallery shows. One was scheduled right when I began at Clearcover and a bunch of Clearcover employees showed up to support me. I was happy to see them—and surprised that they’d turn out for a new person they barely knew. But that’s the Clearcover way.

Clearcover is scaling fast but our culture is special. We’re doing unique and interesting work with fantastic people, and we’re always looking for new talent to join the team.

Could that be you? Check out Clearcover’s open jobs!