Spinning Thimble Logo

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
Thimble team photo

Get in on a game-changing company.

Thimble is a rapidly growing, well-funded insurtech startup led by three-time entrepreneurs Jay Bregman and Eugene Hertz. We’ve raised $45 million in funding from IAC, OpenOcean, Slow Ventures, and other top firms. 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.

Sharing a spreadsheet

Be an owner.

Our Monday meetings aren’t your average All Hands. You’ll get to see everything from our financial statements to our fundraising 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.

Remote work

Work in your sweatpants.

Our 100% remote team cross-collaborates all over the US and Xiamen, China. 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 sweatpants first).

Virtual cocktail class

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

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

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.

Diversity, equity and inclusion

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


Dylin H

Associate Product Manager
Madison, WI

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.

Customer Success Representative
San Mateo, 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.

Web Developer
Brooklyn, NY

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.
Suho Song

Suho S.

Senior Product Designer
New York, NY

Feeling proud to be a part of Thimblers who are making a positive/disruptive impact on the industry. There are great growth opportunities at Thimble, as well as collaborative teamwork with some of the brightest minds in the business, and a supportive work environment.

Pets You’ll Meet (on Zoom)

Allie Agatha BrooklynNY


Brooklyn, NY

Min MickeyMew FallsChurchVA

Mickey and Mew

Falls Church, VA

Dave Phoebe BrooklynNY


Brooklyn, NY

Jodi Gunner Shaw WoodstockCT


Woodstock, CT

Anya Arlo SeattleWA


Seattle, WA

Daniela SimonPepper PhoenixAZ

Simon and Pepper

Phoenix, AZ

Deb Spud Therrien VernonCT


Vernon, CT

Dylin Stitch MadisonWI


Madison, WI

Eugene Ozzie Briarcliff Manor NY


Briarcliff Manor, NY

Hank Bear PhiladelphiaPA


Philadelphia, PA

Heather Moogie ChicagoIL


Chicago, IL

Jason Loulou BrooklynNY


Brooklyn, NY

Lily Queenie CharlotteNC


Charlotte, NC

Mike Luna HobokenNJ


Hoboken, NJ

Sam Rosie Ivy DallasTX

Rosie and Ivy

Dallas, TX

Suki LilyMurray TampaFL

Lily and Murray

Tampa, FL

Taylor Goliath MariettaGA


Marietta, GA

Tiffani Cortado AustinTX


Austin, TX

Vivian Nobu SanMateoCA


San Mateo, CA

Perks + Benefits


Comprehensive health, vision, + dental coverage


28 days off + 10 company-wide holidays + 1 Volunteer day

Work from home

Work from home full-time


Your choice of Mac or PC

Coworking space

Co-working space reimbursement


Wellness reimbursement + ClassPass credit


Health perks including One Medical, Teladoc, Talkspace, and Health Advocate


Childcare reimbursement

Open Roles