About Thimble
We’re an insurance broker, founded in 2015, offering coverage for small businesses and independent workers in over 140 professions, including handymen, landscapers, DJs, artisans, photographers, retailers, and small contractors.
We operate online, through a mobile app, and over the phone. Customers can buy or change policies by the job, month, or year, and adjust, pause, or cancel coverage as needed. Our products include General Liability, Professional Liability (Errors & Omissions), Business Equipment Protection (Inland Marine insurance), Business Owners Policy (BOP), Commercial Property Insurance, and Workers’ Compensation. These policies are backed by partners like Markel, National Specialty Insurance Company (both “A” Excellent by A.M. Best), Employers Insurance Group, and Coterie Insurance Agency.
We’ve covered over 151,000 small businesses and issued more than 250,000 policies. 75% of our customers are first-time business insurance buyers. Customers rate us highly: 4.7⁄5 stars on Trustpilot, 9.8⁄10 on Delighted, and 4.8⁄5 on the App Store.
Mission & Values
Our mission is to simplify insurance for small businesses. We live by a set of values:
- Think Wild, Act Tame: Be creative and innovative, but always compliant.
- Green Means GO: Act, move forward, and learn.
- Simplify, Simplify, Simplify: Communicate clearly and concisely.
- Own Every Detail: Be precise and disciplined.
- Every Moment Counts: Be punctual and use time efficiently.
- Stay Human: Promote respect, diversity, and inclusion.
Team & Culture
We’re a fully remote team across the United States, with 11-50 employees. We believe in transparency, sharing our financial statements and objectives so everyone feels a sense of ownership. We prioritize collaboration, technical excellence, and open communication.
We support work-life balance and build community through virtual events, social Slack channels, and employee resource groups like Queer at Thimble, Thimble Ladies, and a Diversity, Equity, Inclusion, and Belonging committee. Our leadership is headed by three-time entrepreneur Jay Bregman, and we pride ourselves on having “no big egos,” high trust, and open communication.
Benefits & Perks
We offer a comprehensive benefits package for our full-time remote employees:
- Health & Wellness: Health, vision, and dental coverage. Access to services like One Medical, Teladoc, Talkspace, Kindbody, and Health Advocate.
- Retirement: A 401(k) plan with auto-enrollment after 90 days. We match 100% of your first 3% and 50% of the next 3%.
- Time Off: 20 vacation days, 8 floating days, 12 company-wide holidays, 1 Volunteer Time Off (VTO) day, and unlimited sick time.
- Parental Leave: 12 weeks of 100% paid leave, followed by a 2-week gradual return.
- Work-Life Balance: “Thimble Fridays” (out of office by 12:00 pm local time).
- Work Setup: Your choice of Mac or PC computer, and reimbursement for home office setup.
- Monthly Allowances: For co-working spaces and/or childcare, ClassPass credit, and quarterly wellness reimbursement.
- Team Engagement: Virtual events, happy hours, and trivia to build community.
Frequently Asked Questions
Thimble provides business insurance policies for small businesses and independent workers. These include General Liability, Professional Liability (Errors & Omissions), Business Equipment Protection (Inland Marine), Business Owners Policy (BOP), Commercial Property Insurance, and Workers’ Compensation. Policies can be purchased by the job, month, or year and are customizable.
Thimble offers comprehensive health, vision, and dental coverage, a 401(k) with matching contributions, and a generous PTO policy including 20 vacation days, 8 floating days, unlimited sick time, 12 company holidays, and 12 weeks of paid parental leave. Additional perks include “Thimble Fridays” (half-day Fridays), home office setup reimbursement, monthly co-working and/or childcare reimbursement, wellness stipends, and access to health and wellness services like One Medical and Talkspace.
Thimble operates as a fully remote team across the US. The culture emphasizes transparency, with financial statements and company objectives shared with all employees. It promotes collaboration, open communication, and work-life balance. Employees are encouraged to form resource groups, and the company organizes virtual events and occasional in-person meetups to foster community.
Thimble supports small businesses by offering flexible and customizable insurance policies that can be bought, modified, paused, or canceled instantly online, in-app, or over the phone. They cater to over 1,000 activities and 140+ professions, providing essential coverage like General Liability, Professional Liability, and Workers’ Compensation, allowing businesses to secure coverage by the job, month, or year to fit their specific needs and growth stages.
Thimble was founded in 2015.
Thimble is active in the Insurance, Independent Workers, Small Business, Handymen, Contractors, Landscapers, Crafters, and Artisans markets.
Thimble has 11-50 employees.
Thimble hires in 🇺🇸 United States.
Yes! Thimble is actively hiring with 2 open remote jobs available now.
Yes, Thimble is a remote-first company.
Thimble's website is www.thimble.com .
You can find Thimble on X (Twitter) , Facebook , and LinkedIn .
2 remote jobs at Thimble
Explore latest remote opportunities and join a team that values work flexibility.
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