Change the future of insurance.

Change work. Change lives.

Thimble’s mission is to make insurance simple, to help businesses succeed on their own terms. To do this, we’ve built a new insurance stack – from the ground up – designed to tackle the uncertainty of starting, running, and growing a modern business.

How does it work? Answer three simple questions and we instantly deliver a certificate of liability insurance straight to your phone. Available as a monthly subscription or tailored to a single job, Thimble is designed to fit your business and seamlessly grow with your ambitions. You won’t need to call us because you’re always in control: scale up, modify, and even pause or cancel your policy with a single tap.

Thimble is one of the fastest-growing small business insurance services in America. We’ve sold over 125,000 policies representing over $150B in coverage since launching in 2016. Over 1,000 customers have rated our apps with an average of 4.8-stars. Money.com honored Thimble as the Best Business Insurance for 2020 .

Founded by three-time entrepreneurs Jay Bregman and Eugene Hertz, Thimble is a remote-first company based in New York City. We’ve raised $30 million in funding from IAC (NASDAQ: IAC), Slow Ventures, and other top firms. 

Ready to take on your next opportunity? Join Thimble and help us shape the future of work.

Current Openings

What We Offer Our Employees

Thimble is a rapidly growing, well-funded InsurTech startup chasing a $250 billion market. Led by seasoned founders with experience disrupting the ecommerce and ridesharing spaces, working with us means learning from innovative, savvy industry experts at the top of their fields.

Benefits & Company Culture

  • Comprehensive health, vision, and dental coverage
  • 20 days paid vacation plus company-wide holidays
  • Virtual trivia and field trips
  • Competitive pay
  • Generous stock options
  • Hardware of your choice

We Support Professional Growth

We are committed to hiring top talent, and we want you to be just as invested in helping Thimble grow. That’s why, in addition to competitive pay, we offer generous stock options to every employee and the opportunity to pursue professional learning opportunities that enrich your career.

We also provide each employee with the hardware of your choice (not drawing any hard lines in the sand here — we believe in a peaceful coexistence between Mac and PC aficionados!).

We Work (and Play) as a Team

We foster an open and agile working environment in which collaboration and communication are encouraged. When we’re in the office, we have a weekly all-hands standup that doubles as bagel Monday. We have a “come as you are” policy in terms of dress code, but our house dog Zoey always looks fly. While we all temporarily work from home, we make sure to get in the quality time with our coworkers over a friendly game of Friday afternoon Trivia.

We Prioritize Work-Life Balance

We rise and grind, but we also relax and unwind. We know how important it is to take time for ourselves, and we offer 20 days of paid vacation plus company-wide holidays so that our employees can do just that.

In addition to our generous vacation policy, we believe that maintaining your health & wellness should be as easy as coming to work. In the name of stress-free healthcare, we offer comprehensive health, vision, and dental insurance coverage to you and your family members.

We Promote Diversity & Inclusion

Inclusivity and diversity among our teammates is crucial to building a better company and better products. Thimble is an Equal Opportunity employer. We do not discriminate based upon race, color, religion, gender (including pregnancy, childbirth, or related medical conditions), national origin, age, military service eligibility, veteran status, sexual orientation, gender identity, gender expression, marital status, disability, or other protected class. We celebrate workplace diversity and are committed to creating an inclusive environment for all employees.

Learn more About Us.