Clearcover's 5th Anniversary, Part 1: Looking Back with Our First Employee

Happy Anniversary to us! This November marks the fifth anniversary of Clearcover's founding and, to celebrate, we're taking a moment to look back at how far we've come since a staff made up of three employees founded the company in our Chicago headquarters in 2016. We've grown in size, launched in nearly half of the country, continue to secure funding, and Clearcover-ers now work in every region of the United States.

The most visible example of our rampant growth is the remarkable increase in the size of our staff. Clearcover launched in 2016 with only three employees and, just two years later, had grown to a substantially larger group of 45. As staggering as that increase seemed at the time, we continued to add to our team, reaching 127 employees in 2019, and 207 in 2020. Unhindered by the Pandemic, we continued to fill open positions, and our ranks currently stand at 402 Clearcover-ers.

All of the founding employees and a majority of those hired during the first two years were based in our downtown Chicago headquarters. As Clearcover launched our insurance products in more states across the country, we've substantially added to our remote workforce. While our insurance products have launched in 18 states with plans for further expansion, Clearcover-ers currently reside in 27 states across four time zones.

All of this growth has only been possible with the funding Clearcover has secured at several points since 2016. We first secured $11.5 million of Series A funding in 2017 followed by $43 million of Series B in 2019, $50 million of Series C in 2020 and, most recently, $200 million of Series D funding this year.

While all of these statistics concretely quantify Clearcover's growth over five years, the best way to get the full picture of what the expansion has felt like internally is to speak to someone who has witnessed it all first-hand. Matt Dressel, Clearcover's VP of Organizational Development and one of the first three employees to join the company in 2016, was gracious enough to look back and share what originally drew him to Clearcover, some of his most memorable milestones, and how our culture has remained consistent over the last five years.

What first drew you to Clearcover? What made you want to be part of the launch of this particular start-up?

I was working at another successful Chicago startup and had made myself a nice career there when I was introduced to Kyle in Sept 2016. I had two young children at the time, was not looking for a new job, knew nothing about insurance and was fully under the impression I would just be giving Kyle some thoughts about what it might take to build insurance software in Chicago.

So, have you ever met Kyle? Within a week of meeting Kyle, I was discussing how I might be able to help him launch Clearcover. I wanted to work at Clearcover because of Kyle - not because I wanted to join an early startup. When I met Derek, it was icing on the cake. Derek provided all the insurance industry expertise that Kyle lacked. The two co-founders were humble, honest, attentive listeners and ready to work harder than they ever had before to ensure this new company’s success. I felt incredibly energized and knew I had to take this chance.

Can you describe the feeling among Clearcover employees when you launched in your first state?

Unbridled enthusiasm and immense pride. Our company was small - nearly the entire company fit into a small room and we all watched the first sale in real time. Our handful of customer advocates worked the phones with Adam Fischer. Smiles and hugs all around.

The preceding year, 2017, was a true highlight of my career and I believe most of the early Clearcover employees feel similarly. We all took risks to join the company, but we also knew we had exceptional leadership, product vision and a tight-knit collection of individuals who all were amazingly capable. We shared many nights and weekends working together pushing through a mountain of work. We all sacrificed a lot in our personal lives to get California launched, but I think we also felt extremely fulfilled that we were able to accomplish what we did with a truly wonderful group of people who all really cared about each other and cared about making a real impact in this world.

Over the past five years, what has felt like Clearcover's biggest milestone?

This is a pretty difficult question to answer because the entire first three years were filled with giant milestones: launching states, new partnerships, raising money, hiring key employees - we had a bell in the office that we would ring whenever a milestone was achieved. We rang it quite a bit. With that said, there is one milestone that I believe will have the most profound impact on our Company’s future success - development of our own policy administration system. We will not be able to tackle the vision we have for our company without owning our entire insurance software stack. I am really proud of what my colleagues have built and I think it will be the fulcrum that provides the necessary leverage for our future milestones.

Clearcover has grown from 3 to over 400 employees. During that exponential growth what, in your opinion, has remained constant?

It’s an interesting question, because I almost always think about what has changed. Collaborating at a single table with the entire company is very different from working truly remotely with many, many more colleagues all across the country. When thinking back at the individuals at that table, it becomes obvious one thing that’s constant - the caliber of Clearcover employee. Many of my colleagues sought out Clearcover because they were looking for a work culture that appealed to them, a product that could make a difference and a place where they can learn, teach and grow. We have attempted to create an environment since the beginning that:

allows people to do the best work of their lives
encourages transparency, collaboration and accountability
shoots for goals that seem beyond our reach
supports our ability to create a great product for our customers
treats all of our employees with the respect and care they deserve

We have had to change the tactics used to create this atmosphere over time, but we consistently hire wonderful, talented people.

What is your favorite tradition at Clearcover?

Wins. It’s hard to tell from the name everything that it encompasses. As we have gotten bigger, it’s no longer the same experience as when we all fit into a corner of the office. But the premise of this tradition at Clearcover is an opportunity to periodically celebrate achievements and publicly share gratitude. The achievements are a source of pride and praise - all public in front of the entire company. We work really hard and we don’t always know what the rest of the company is working on. “Wins” helps us share these achievements.

We also share failures in the form of the banana award. Pre-COVID, we would hand out a stuffed banana that would travel from recipient to recipient. Only an employee-themself indicates they want to be the recipient and discusses why they deem themselves worthy of the award. This award is meant specifically for moments where we took a good-intentioned risk, but failed. Kyle wants us to take risks even if they sometimes lead to failure. As a secondary benefit, we see leaders and colleagues admit that they failed in a public forum. Failure is universal, but frequently kept hidden due to perceived or actual professional ramifications.

Finally, “Wins'' is also an ad hoc forum of gratitude. I believe this has a profound impact on the connectedness we feel as a company. Letting others know that they had a positive impact on your life - work or otherwise - strengthens the fibers of connectedness between individuals and across the entire company.

We have shared many emotional moments during wins. Shout outs, hugs, tears and joy. This tradition, despite its changes over the years, has a special place in my heart.

How would you describe Clearcover's culture to someone outside of the company?

This is another interesting question to reflect on. It may seem like an easy one to answer, but it’s not. Culture is not something permanent, as the vibe of the company is greatly influenced by all the people who make up the company - including, and most importantly, all the new employees. We certainly have guidelines, mental models and frameworks that provide structure and expectations around the way we work and interact, but the culture, as long as it lives within these boundaries, is fluid. Early on, the company was more of a mono-culture, where we had only a handful of people influencing how the company “feels”. I felt more certain I knew our culture back then. I have learned that people can have very different needs out of their company and approach work in different ways than I do. The company, likewise, has different needs out of its employees over time. We have trust that our employees will have a positive impact on our company and a side effect of this may be a culture that shifts. This is not only ok, but is encouraged.

Matt's reflections on Clearcover's five year history paint the picture of a company that, through a period of incredible growth, has continued to set and attain loftier goals and reach milestone after milestone, all while maintaining a culture that values its people by celebrating their successes, expressing gratitude, and allowing them to do their best work. If you're interested in being part of Clearcover's next five years and beyond, we invite you to apply for one of our open positions.

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