2022 Year in Review

Written by Team Clearcover

As 2022 comes to a close, we’re excited to continue our annual tradition of reflecting on the great year we’ve had and celebrating our organization’s accomplishments. Last year, we highlighted our record growth and the launch of our customer-centric brand refresh. We entered 2022 enthusiastic about our goals for continued growth and development, and it’s been incredible to see how we’ve delivered on those goals this year. 

We Launched Car Care

In January, we launched Car Care—the first offering of our new Clearcover Advantage™ benefit. Through Car Care, we provide value to our customers beyond the great car insurance coverage they get as Clearcover policyholders. Car Care makes car maintenance easy and affordable through discounted maintenance and repairs, personalized maintenance reminders, recommended maintenance schedules, real-time price comparisons and booking, and more. The Clearcover Advantage™ team has made huge strides this year in the development and implementation of Car Care and have continued to work hard all year to further enhance the Car Care program. We launched Car Care in six states this year and will have more states joining the list in 2023. 

We Thought “Better-er” at Our First Hackathon Event

In May, we held our first ever hackathon event, Clearly Hacked. Over the course of one very busy week, Clearcover engineers aligned with our Leadership Principles—like Thinking “Better-er”—and formed over twenty teams to build solutions to perceived problems within our existing systems and processes. We had fantastic participation and are already looking forward to Clearly Hacked 2023. 

We Were Inspired

This year, we wrapped up our Inspired Underdogs sponsorship program with twenty new NCAA athletes. As underdogs ourselves, we’re inspired by the unique stories of these college athletes and their collective passion, resilience, and dedication.


We Were Recognized for Who We Are and What We Stand For

We turned six this year and grew to over 570 employees across 36 states. With all the growth we experienced, we remained committed to making Clearcover a great place to work. Purpose Jobs recognized these efforts and named us one of the 100 Best Places to Work in Midwest Tech and one of the Best Places to Work in Chicago. Built In Chicago followed suit by naming us one of the Best Places to Work in 2022, one of the Best Midsize Companies to Work for 2022, and one of the Best Paying Companies in Chicago.

We were recognized for our growth by making the Inc 5000 list of fastest-growing companies in America and the Deloitte Technology Fast 500 list of fastest-growing public and private companies in North America. Our tremendous growth would not have been possible without our people. Thanks to our extraordinary team members, we won four Comparably awards, including Best Product & Design Teams and Best Engineering Teams


We were honored to win a BBB Torch Award this year that reflects our commitment to building trust with our customers. According to BBB President and CEO, Steve Bernas, “Torch Award winners demonstrate extraordinary ethical standards of trust and behavior. These companies represent the highest level of dedication to four key attributes including character, culture, customers, and community.”

We Made the News

Built In Chicago interviewed Brent Walker, who was named Chief Technology Officer this year. In the interview, Brent shared how Clearcover managed the speedy expansion of our engineering team. Insurance Thought Leadership sat down with Kaitlyn Taylor, Director of Agency Accounts, for insights about agents and technology, and Director of Engineering, Sangeeta Shah, shared her experience as an influential woman in leadership and provided advice for aspiring managers in a Built In Chicago article.

We Supported Each Other

At Clearcover, our people-first culture is integral to our identity. The vast array of viewpoints and opinions our employees bring to their work is one of our strongest assets, and we are committed to helping all “Clearcover-ers” feel supported. This year, our Equity, Inclusion, and Diversity Council (EIDC) made community and belonging even more accessible by introducing four new Employee Resource Groups (ERGs): the Clearcover African American Network (CAAN), Sage Solace, Parents of CC, and Women in Insurance and Tech (WIIT). 

For these efforts and more, Crain’s Chicago Business named our Chief People Officer, Vikki Caruso, one of Chicago's 2022 “Notable Executives in HR and Diversity, Equality and Inclusion.”

We Raised Money for What Matters

We came together to support men’s health this year by raising over $10,000 for Movember. It was our second year aligning with Movember, an organization that addresses the crisis in several areas of men's health, including mental health and suicide prevention. Exceeding our fundraising goal also meant we got to see Clearcover CEO Kyle Nakatsuji and COO Derek Brigham get all jazzed up for a Night at the Roxbury-inspired photoshoot

We also showed up strong for Breast Cancer Awareness Month. We challenged “Clearcover-ers” to collectively raise $5,000 for the American Cancer Society during the month of October. Through the sale of our Clearcover Breast Cancer Awareness t-shirts, our participation in the American Cancer Society's Making Strides 5Ks across the country, and the SnackMagic stipends that were donated by over 150 employees, we surpassed our goal by raising a combined total of $8,543.

We’re Geared Up for an Awesome 2023 
As we head into 2023, we remain fiercely committed to continuing on our mission to become the digital auto insurer of choice. We’re grateful for our team of resilient, hard-working “Clearcover-ers” and are excited for what’s to come, our continued growth, and all the things we’ll accomplish together.