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Thimble

On-demand insurance for freelancers, self-employed, and small businesses

Thimble logo
21-100 employees
  • Fintech
  • B2B
  • Insurance
South Village, New York, NY

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Company mission

Thimble is on a mission to make insurance simple, on-demand, instant, and flexible.

Our take

Thimble brokers quick, short and long term insurance to small businesses and gig economy professionals in minutes. All purchasers have to do is answer three questions on their platform before gaining access to deals that can cover one hour up to full monthly plans.

Until 2019 the company, which was started by Hailo founder, Jay Bregman, was known as Verify and focused on providing insurance to drone pilots. The rebrand comes after they added many more types of insurance for a variety of businesses. Now they’re covering upwards of 100 lines of work including DJs, musicians and beauticians. Indeed, around 75% of Thimble’s customers did not previously have insurance, and close to half bought a single day of cover.

They raised $22m in Series A from investors such as AXA Venture Partners and Slow Partners in 2019. This money was used to transform the product, allowing the startup to tap into the more transactional nature of modern work, close to 60 million people now freelance in the USA, a number which is expected to rise to above 85 million by 2027. As a result, buying an annual insurance policy has become less suitable for millions of workers, it's this niche Thimble hope to exploit further in the future.

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Steph

Company Specialist at Welcome to the Jungle

Benefits

  • Your choice of Mac or PC
  • 23 days PTO + company-wide holidays
  • Comprehensive health, vision, + dental coverage
  • Work from home full-time
  • Co-working space reimbursement
  • Wellness reimbursement + ClassPass credit
  • Health perks including One Medical, Teladoc, Talkspace, and Health Advocate
  • Competitive salary + equity

Company values

  • 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

Funding (last 2 of 3 rounds)

Oct 2019

$22m

SERIES A

Oct 2017

$4.2m

SEED

Total funding: $28.9m

This company has top investors

Leadership

Jay Bregman

(CEO)

Studies Politics & Philosophy at Oxford, a Masters in Media at LSE. Founder & CTO of eCourier.co.uk. Founder & CEO of Hailo.

Eugene Hertz

(CTO)

Director of IT at The Topps Company for 4 years. Chief Information Officer at Quidsi Inc for over 4 years.