What’s it like to be an engineer at Clearcover?

By Sunny Vempati  3 minute read

By Sunny Vempati

3 minute read

Okay, let me set this up. It's midnight on a cold Wednesday. The entire engineering team is huddled in our little office in River North. The ceiling has only recently stopped leaking from a storm earlier in the week. At home, our families are sound asleep (dog, in my case).


It's been months of tough work and long hours. We still have yet to sell a policy—in fact, we haven’t even sold a fake policy to ourselves. We’re so close now. The minutes tick by.


We see the confetti—the famous confetti!—and the “Congrats!” screen. Finally, we have bought a test policy on our platform!

And that was the moment it started to feel real—we were going to launch Clearcover, and it was going to be epic!


We promptly went to get celebratory doughnuts, and this photo was taken a few moments later. A few key team members had to be (badly) photoshopped in.


This little (but really significant) win provided all the momentum we needed to help launch the company and nurture the growth of one of the best engineering teams I've ever worked with.

When I describe the Clearcover engineering team to friends and family, it’s hard to put into words everything that makes it so special. So this is my attempt.

1. The perfect combination

I've worked with many engineers over the past decade. I’ve never thought much about the qualities of what makes an ideal teammate besides the importance of intelligence. Clearcover quickly taught me that being an experienced developer just isn't enough.

For a software developer to take the next step in their career, they need to be able to communicate effectively but with empathy. Clearcover engineers taught me this in spades. Yes, we were all hired because of our depth of knowledge, but the way we communicate with each other has truly been the trait that allowed us to thrive as a team. It's allowed us to incorporate good design principles, learn new architectural patterns, and adopt languages (like Scala!) that we may never have otherwise.

We've had very contentious architecture discussions, but we've come out of these discussions with different perspectives and a stronger bond. Most importantly, we all learned something new from each other. Instead of asking, “How can I prove my solution is the best?” We align ourselves with another question, “Under the current circumstances, what is the ideal solution for the problem at hand?”

2. A unique opportunity

When you're trying to break into a highly regulated industry, engineering creativity often takes a back seat and ends up being very constrained in its capabilities. But the leadership at Clearcover provided the engineering team with an incredible opportunity to build solid frameworks and an easy-to-use platform—while they managed the world of regulations. They gave us the freedom to build software the way we wanted to, guided by our North Star of saving time and money for the customer.

This unique opportunity isn’t taken for granted. We're trying to prove that we can be a successful company in the insurance space. We’re using technology to provide the best experience for our customers. The inherent motivation that comes with this type of opportunity is the key to the happiness of the engineering team at Clearcover. Knowing you're surrounded by highly motivated individuals who are bound by a common goal makes the mountain climb much easier.

3. Friday Wins

Every Friday, the entire company gets together for a "Friday Wins" meeting. The goal of the meeting is to acknowledge and share the wins we've experienced throughout the week. We've done this since the early days of the company, and what's interesting to me is how the meeting has evolved since then.

The Friday Wins began as a meeting where everyone shared their small to big wins for the week, but, as we hired more people, the wins ended up becoming shout-outs to others. Personal wins became just a side note.

I love how Clearcover team members use this meeting to highlight the successes of others and acknowledge how others' work affect them positively. It’s a testament to everyone that works at Clearcover. What a good feeling to know that everyone is rooting for you and excited enough to share your wins with the entire company. This meeting is just one example of the many reasons that I feel optimistic for the future of Clearcover and our team.

Instead of asking, “How can I prove my solution is the best?” We align ourselves with another question, “Under the current circumstances, what is the ideal solution for the problem at hand?”

Our biggest accomplishment so far isn't the great product we've built or our successful launch, it's the team we've put together. Launching this company was about building relationships with each other.

All of us are very aware of the culture we've built at Clearcover. We're protective of it. As we grow out of the startup phase, there's reason to be highly confident that we'll be able to scale and continue to enhance our culture as we grow.

I realize that the engineering culture at Clearcover is still in its honeymoon phase and we have many more challenges ahead. But this post is to highlight how special of an opportunity we have ahead of us and how excited and happy I am that I'm part of this journey. Let's keep this ball rolling!

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