Change the future of insurance.

Change work. Change lives.

Thimble’s mission: we make insurance simple, enabling small businesses to succeed on their own terms. We work hard to make it easy for over 100 professions including handymen, DJs, pet sitters, beauticians, and more to get insurance and take on that next opportunity.

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
  • Lower East Side office (and a cute house dog!)
  • Bagel Mondays & team outings
  • 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

Our office is located in the heart of the Lower East Side, with great lunch spots, shopping, and coffee shops within walking distance. We have a “come as you are” policy in terms of dress code, but our house dog Zoey always looks fly.

We foster an open and agile working environment in which collaboration and communication are encouraged, with a weekly all-hands standup that doubles as bagel Monday. We also encourage out-of-office team bonding with regular happy hours in the neighborhood.

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.

Verifly is now Thimble! Hello! We've updated our experience and changed our name to Thimble. If you have any questions, please reach out to support@thimble.com