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, 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.

Details

Own Every Detail

Be ruthlessly precise. Disciplined. Sweat the small stuff.

Moment

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.

Human

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

Mariah Casillas

Mariah C.

Broker Development Manager
Skiatook, OK

My fellow Thimblers are passionate, talented and down right hilarious! We have weekly all hands meetings where our leaders are transparent about how the company is doing and what our future looks like. Thimble prioritizes inclusion and work life balance, which creates a positive work atmosphere for all. Being a part of Thimble is a dream come true.
1566589890209

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.
Hailey Park photo

Hailey P.

People Operations Coordinator
Queens, NY

At Thimble, I get to work with innovative and supportive coworkers. Everyday I get to learn something new and it’s a great environment for your professional growth. Although we are a remote company, Thimble has a great way of keeping the employees engaged through slack, virtual events, and even meeting IRL that keeps it fun!
Vivian

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

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

Agatha

Brooklyn, NY

Min MickeyMew FallsChurchVA

Mickey and Mew

Falls Church, VA

Dave Phoebe BrooklynNY

Phoebe

Brooklyn, NY

Jodi Gunner Shaw WoodstockCT

Gunner

Woodstock, CT

Anya Arlo SeattleWA

Arlo

Seattle, WA

Daniela SimonPepper PhoenixAZ

Simon and Pepper

Phoenix, AZ

Deb Spud Therrien VernonCT

Spud

Vernon, CT

Dylin Stitch MadisonWI

Stitch

Madison, WI

Eugene Ozzie Briarcliff Manor NY

Ozzie

Briarcliff Manor, NY

Hank Bear PhiladelphiaPA

Bear

Philadelphia, PA

Heather Moogie ChicagoIL

Moogie

Chicago, IL

Jason Loulou BrooklynNY

Loulou

Brooklyn, NY

Lily Queenie CharlotteNC

Queenie

Charlotte, NC

Mike Luna HobokenNJ

Luna

Hoboken, NJ

Sam Rosie Ivy DallasTX

Rosie and Ivy

Dallas, TX

Suki LilyMurray TampaFL

Lily and Murray

Tampa, FL

Taylor Goliath MariettaGA

Goliath

Marietta, GA

Tiffani Cortado AustinTX

Cortado

Austin, TX

Vivian Nobu SanMateoCA

Nobu

San Mateo, CA

Perks + Benefits

Coverage

Comprehensive health, vision, + dental coverage

Vacation

23 days PTO + company-wide holidays

Work from home

Work from home full-time

Laptop

Your choice of Mac or PC

Coworking space

Co-working space reimbursement

Fitness

Wellness reimbursement + ClassPass credit

Health

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

Equity

Competitive salary + equity

Open Roles