Clearcover in 2020—Addressing challenges with creativity and resiliency

It’s Clearcover tradition: At the end of each year, we look back at everything that happened—the things we accomplished, the strategies that worked (or didn’t work!), and the lessons we learned. In 2018, our CEO, Kyle Nakatsuji, wrote about what it was like to start an insurance company from scratch, and last year, I wrote about keeping our culture while tripling the size of our team.

But this year? This year presented challenges we never could have imagined in 2019, and that’s why our story of this year is one of adapting quickly, getting creative, and making things happen in the most unexpected of circumstances.

Here’s what we learned this year:

Supporting our employees is core to who we are.

For all the groundwork we’ve put in regarding our culture up to this point, the events of 2020 presented a unique challenge we never could have anticipated. Our key finding this year: Empathy is key. It became clear very quickly that we needed to find as many ways as we could to actively listen to and support our employees. We didn’t know their challenges, so we needed to let them tell us and be ready to change our support strategies as necessary. Here are three strategies we found successful:

We took the remote work transition seriously from the start.

Taking care of physical and logistical needs during the transition was a big first step toward supporting our team. We worked overtime to ensure everyone had a comfortable office chair and a good place to work at home. We also retooled our working strategies to ensure everyone had the flexibility they needed to juggle childcare, family life, and work responsibilities.

We made diversity and inclusion a priority.

We want every member of our team to feel safe and supported—and we knew we’d need some help to make that happen. So in 2020, we elevated the role of our diversity and inclusion committee and brought in an outside expert to train our employees on racism and implicit bias. We know that levelling the playing field and creating a safe workplace is a long term project, so our expert now leads our D&I committee and is in constant communication with senior leadership at Clearcover to provide needed perspective and to help drive inclusion efforts.

We provided expanded mental health care services.

We made sure every member of our team had access to the mental health support they needed to survive during 2020, and began an official #mentalhealth channel in our company’s Slack channel so that employees could talk about their mental health concerns openly. We also brought in mindfulness speakers and provided group yoga, meditation, and counseling sessions for all who were interested.

These steps were important—our first priority is always the health and wellbeing of our team—but they weren’t enough. Next, we needed to figure out how to run a successful company under a totally new working environment.

Remote work doesn’t mean disconnected work.

We built a strong team foundation for remote work—even before COVID hit. 30% of our employees were already working remotely, and we made a point of bringing them onsite on a regular basis. We also had a remote work committee that was in charge of ensuring our remote workers fit into the life of the company seamlessly.

When the lockdowns hit, though, we kicked our communication strategies into high gear to ensure that no one felt lonely or disconnected. Because none of our team members were physically in the same space anymore, we made an extra effort to facilitate cross-team communications.

And we did plenty of fun stuff, too. We hosted a mug exchange. We sent out snack boxes to each of our employees. And—when it was time to celebrate big accomplishments—we hosted online parties and shipped identical gift boxes out to every member of our team so that everyone could feel like they were a part of the fun.

In short, we did everything possible to keep our team connected.

We can build our team with excellence—even in the midst of uncertainty.

The Clearcover team doubled in size in 2020. Since the start of the pandemic alone, we’ve hired 122 team members, including two C-suite executives. And because of our unique situation, we needed to onboard every single new employee remotely, including employees who would be leading teams of people they’d never met in person.

So we adapted! Throughout the year, we developed many strategies to help our new team members feel integrated and comfortable as quickly as possible, despite the physical distances involved. We instituted happy hours and lunch talks with managers to help everyone feel acquainted and to make sure our leaders formed great relationships with their new reports. We also sponsored lunches where new employees could meet our senior leadership team to ask questions and get to know the culture of the company.

All of this was a challenge, but our efforts have paid off! Feedback from our new hires has highlighted the excellence of our remote onboarding strategies, and we’ll continue to iterate on these strategies as we hire and onboard remotely in 2021.

If we address challenges with creativity, we can accomplish big things.

Despite the uncertainty of 2020, our team got some spectacular wins. Here are some of our biggest things we achieved:

We raised $50 million in Series C funding round.
We launched Clearcover in seven new states—yes, seven.
We introduced our internal policy management system.
We supported our customers during COVID-19 in offering premium rebates where we could, as well as providing gifts to our customers who are healthcare workers and first responders.
We launched Clear Claims™, the fastest claims experience in the car insurance industry. (Our current Clear Claims payment record? We recently issued payment in just 13 minutes.)
We won several awards for our team culture, including Built In Chicago Best Places to Work, Comparably’s Best CEO, Glassdoor’s Best Places to Work, and Inc’s Best Work Places.
Our product team won a Mobile Web Award for the Clearcover app—the second year in a row we’ve won an award for our mobile app.
We adopted a school as a company and collected $10,000 for charity.

Perhaps the biggest achievement of all is that we accomplished all of this while working entirely remotely. (We made sure to celebrate these milestones, too—albeit at a distance!)

The biggest lesson of 2020—and what we’re taking into the new year.

This was certainly a year no one could have foreseen, but working through it and facing the challenges together has taught us a lesson you can’t get from a book: resilience.

Among our core values are Accomplish more with less and Execute with urgency and focus—and we’ve never had a better test of these values as a company. We needed to execute with urgency and accomplish more with less because we didn’t have a choice. Although 2020 was a tough year, I’m proud to look back on all we accomplished.

I’m also excited about the strategies we’re taking with us into 2021! For example, we plan to keep being champions for the mental health of our team, and we’ll continue to expand the programs we built to address pandemic challenges. We’ll build on the success of our remote hiring, but with even more flexibility and with new hybrid remote schedules so our team members can work whenever suits them best. And we’re also envisioning new and exciting ways to work together in the future—we’re working with an organizational design consultant who is helping us build an innovative vision of what working at Clearcover will look like in 2021 and beyond.

Beyond all of that, though, the most important thing we’re taking into the new year is the grit, determination, and creativity we built while facing the challenges of 2020. Now we know for sure that we can build this company even in the most trying of circumstances—and it’s that resilience which will most help us to grow and build Clearcover in 2021.