Work with Thimble.

Our mission is to make insurance simple for small businesses. If you’re a nerd for knowledge, love a creative challenge, or have ever been told your ideas are too “out there”...well, let’s talk!

Join our team

Get in on a game-changing company.

Thimble is a rapidly growing, well-funded insurtech startup led by three-time entrepreneur Jay Bregman. We’re a fun-loving squad with a serious passion for supporting small businesses. You’ll work with exceptional people from veterans in the insurance game to experts in consumer tech and self-proclaimed art school kids. Together, our breadth of experiences help us discover innovative ways to push the needle.

Be an owner.

Meetings aren’t your average All Hands. You’ll get to see everything from our financial statements to our objectives and key results progress and get real, honest-to-goodness transparency into every aspect of the company. Why? Because we believe that the more information you have, the more empowered you’ll be to feel like an owner.

Work in your sweatpants.

Our 100% remote team cross-collaborates all over the US. We’ll set you up with a stipend to deck out your home office, wellness perks to help you stay active, plus a co-working space reimbursement for days you need to get out of the house (but maybe change out of those pajamas first).

Build community from home.

At Thimble, we believe work is one part of a robust, fulfilling, balanced life. We enthusiastically support our team making time for what matters, whether that’s bragging on your little one’s first day of school in the #thimblekids Slack channel or taking an hour out of the day to (virtually) meet a new hire Coffee Buddy. We stay connected in work chats dedicated to bonding with our co-workers (#trash-tv is our favorite!) and unique virtual events like safaris and cocktail classes. Occasionally, we’ll organize IRL meet ups to talk about fantasy football and pet each other’s dogs.

What We Value

Think Wild, Act Tame

Be relentlessly creative. Question everything. Get to know the rules so well, you can use them in new ways. Be the industry’s compliant radicals.

Green Means GO

Act. Move Forward. Learn. You can only make a decision based on the best information you have — so make it.

Simplify, Simplify, Simplify

Get to the point. Make it crystal clear. Cut everything else. It’s our job to make insurance easy — however hard that is for us.

Own Every Detail

Be ruthlessly precise. Disciplined. Sweat the small stuff.

Every Moment Counts

Show up early and ready. Deliver on time or before. Make the most of your time, so others can make the most of theirs.

Stay Human

Treat every person, and their ideas, with respect. Cherish diversity.

Our journey to diversity, equity, inclusion, and belonging.

We rethink what’s possible by broadening our perspectives and challenging the norms to support our customers, empower our employees, and revolutionize the insurance industry.

As part of this commitment, we encourage Thimblers to start their own employee resource groups such as Queer at Thimble, Thimble Ladies, and the Diversity, Equity, Inclusion, and Belonging committee, just to name a few. These groups are always working on exciting ways to improve our culture, from organizing charity raffles for our favorite LGBTQ+ organizations to sending out culturally-appropriate small business snack boxes in honor of heritage months.

People You'll Meet

Matt G Lead Full Stack Engineer St Petersburg FL

Matthew G.

Lead Full Stack Engineer
St. Johns, FL

As a member of our engineering team, I work alongside a truly rare group of brilliant, professional, and collaborative folks who make every day productive and enjoyable. Engineering leadership is highly technical and always transparent - there is a high degree of trust and open communication across the entire team, and there are no big egos here. We each have freedom to work across many areas of code to build the best solution, not limited by unnecessary restrictions.

Meena G.

Senior Backend Engineer
St. Johns, FL

Working at Thimble has been a wonderful experience with a team that values collaboration, and technical excellence. As a backend engineer, I've had the privilege of working alongside talented developers, architects and product managers who all share a passion for building high-quality software. The mentorship and knowledge-sharing culture here have been instrumental in my learning and development. I am grateful to be part of a company that values teamwork, technical excellence and continuous improvement.

Dylin H.

Product Manager
Calumet, MI

I get to work with incredibly talented and intelligent coworkers, a transparent leadership team and participate in a company culture that supports the values of its people. All of this while also allowing flexibility and encouraging work/life balance.

Vivian H.

Senior Customer Success Representative
Daily City, CA

Thimble is an amazing company to work for because everyone in the company is friendly, always willing to help, and works together as a team. It’s a great feeling to be proud of where I work. I get to help small business owners and part-time gig workers achieve their business goals so they don’t have to stress too much over what type of insurance they need!

Beth K.

Senior Web Developer
Seattle, WA

At Thimble we have a powerful combination of autonomy and strong mentorship. There are no barriers and plenty of opportunities to take on new challenges. I can learn a new technology and take the lead on integrating it, or get involved in project planning and strategy. This is a great place to grow.

Vee M.

Broker Success Associate
Roseville, CA

Working at Thimble has been an incredible experience! I truly enjoy helping brokers understand our products, and it’s rewarding to see the impact we have. The team’s supportive and energetic vibe makes every day enjoyable. Thimble is a place where learning and development are always encouraged, making Thimble an exciting and rewarding place to work!

Clare N.

Senior Data Analyst
Long Island City, NY

At Thimble, open communication is both appreciated and encouraged. The Data Team is not siloed: each team member assists a variety of stakeholders with their needs. Our full stack approach fosters interdepartmental collaboration, which is a big part of company culture.

I love helping someone get the data they need to answer a question or better understand how the pieces fit together. If you love using data to make business decisions, you will enjoy working here too.