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Best Places To Work: Insurtech Startups

It’s not a coincidence that some of the cities with the biggest insurance headquarters are also home to some of the best insurance disruptors. 

In the Midwest, cities like Chicago and Columbus are home to some of the best insurtech startups, not just in the Midwest but in the country. With huge funding rounds and major IPOs, these insurtech startups are on the map.

Amazing teams, great benefits, and excellent learning opportunities also make these top insurtech startups stand out as amazing places to work. 

So what’s it like working at a Midwest insurtech startup or tech company? Check it out. 

Midwest Tech: Best Insurtech Startups and Tech Companies


Chicago, Detroit
51-200 employees

Clearcover is rebuilding car insurance tech-first. Founded in 2016, the Chicago company has a relentless focus on customer experience (a team that is now based in Detroit) and digital efficiency. Here are a few things people love about working at Clearcover:

  • Great onboarding, even remotely
  • Transparency
  • Learning and growth opportunities
  • The people—genuine support and friendships

Interested in working at Clearcover? They're hiring for open remote jobs and in Detroit. Learn more about life at Clearcover, join the talent community for free, and start applying for jobs at Clearcover. 



Beam Dental


51-200 employees

Beam Dental is revolutionizing dental insurance with their internet-connected toothbrush. Based in Columbus with a growing remote workforce, Beam is one of the top startups in Columbus and one of the best places to work. As the company quickly grew, the Beam engineering and product team alone scaled to 100 employees in less than a year, led by CTO Brian Hough. This rapid growth has led Beam to be constantly focused on culture and education, making it a fantastic place to work and learn. Some other aspects people love about Beam:

  • Diversity & inclusion
  • Great benefits and focus on employee wellness
  • Personal growth
  • Ego-free leadership that’s genuinely supportive

Branch Financial

Branch logo horizontal
1-50 employees

Founded in 2017, Branch Financial is a growing insurtech startup with a family feel. The company is driven in their mission to make insurance (and their startup) powered by the common good. In 2020, they raised $24 million, putting them on the map as a top Columbus startup to watch in 2021. What else makes them notable? Their amazing culture:

  • Personalized mentorship/personal growth
  • Friendly and kind humans
  • Great leadership
  • People have each others’ backs
  • Diversity & inclusion



500-1000 employees

Root Insurance delivers affordable car insurance based on how a driver actually drives. Good driving habits? Good insurance rates. The company went public in the summer of 2020, raising $724 million in their IPO. Here’s what people love about working at Root:

  • Great benefits
  • Competitive pay
  • Challenging but rewarding work
  • Feeling valued


Matic Insurance

Matic logoColumbus
51-200 employees

Originally based in LA, Matic Insurance is a top insurtech startup in Columbus. They have a great company culture based on transparency and teamwork, and they’re one of the best places to work in Columbus. People also love working at Matic for its...

  • Compassionate team—everyone is happy to help out
  • Growth opportunities
  • Lived-out value that everybody matters


Bold Penguin

bold penguin logo
51 - 200 employees

Bold Penguin is a Columbus insurtech startup that's adding a human touch to commercial insurance. The company announced in January 2021 that it was acquired by American Family Insurance, but will retain its name and business model as a subsidiary of American Family. The company has consistently been one of the best places to work. Here's what people love about it:

  • Employees feel valued and cared for by leadership
  • Great learning and growth opportunities
  • Driven by their mission, culture, and vision
  • Engaging and energetic team
  • Diversity & inclusion


Coterie Insurance

10 - 100 employees
Coterie is a Cincinnati startup that offers simplified and accessible insurance to small business owners. The company has been in the news lately for their recent funding round, and they're becoming one of the best places to work in the Midwest. Here's why:

  • Core values are lived out: passion, integrity, humility, intentionality, to name a few
  • Team embraces differences—and they're stronger for it
  • Opportunities for growth



battleface logo
1 - 50 employees

battleface is a leading insurtech startup for travel insurance. The company is based in the UK. However, after a $12 million investment from Drive Capital in December 2020, battleface is establishing its global headquarters in Columbus and building their team. Here's a few reasons why it's the best place to work:

  • Embrace diversity and creativity
  • Corporate social responsibility is one of the key pillars of the company
  • Flexibility
  • Amazing people


Groundspeed Analytics

Ann Arbor
51 - 200 

Powered by innovative AI solutions, Groundspeed Analytics is disrupting the $300 billion commercial insurance industry. This Ann Arbor tech company is also one of the best places to work:

  • Collaborative and inclusive work environment
  • Endless growth opportunities and support from leadership
  • Great people and strong relationships, even during this time of remote work



proformex logo
1-50 employees

Proformex is a small insurtech startup in Cleveland that provides life insurance inforce policy management solutions. The company is building a team that’s hardworking, passionate, and excited about improving the world. Some other notable reasons why working at Proformex is great include:

  • Great and inclusive leadership—the CEO and CTO are women
  • Opportunities to get involved and make a difference in the company
  • Professional growth