Job Details

  • Full Time
  • United States- Remote
  • Posted:

(Commercial Insurance) Underwriting & Compliance Analyst

About Us

Thimble is quick-thinking insurance for fast-moving businesses. We work hard to make it easy for 140+ professions like handymen, landscapers, DJs, artisans, and mall Santas (yes really) to get the insurance they need to take on every opportunity.

It’s the first business insurance provider that puts customers in control: small businesses of any size can get a policy by the job, month, or year from Thimble in minutes and modify, pause, or cancel anytime.

Thimble is simple, scalable, and flexible, which is why we made MONEY Magazine’s 2021 “Best Insurance for Small Businesses” AND we’re Fast Company’s #1 “Small and Mighty” Company. We’re also rated 4.8 out of 5 stars on Trustpilot and the App Store and have sold over 200,000 policies to more than 65,000 small businesses.

Founded by veteran entrepreneurs Jay Bregman and Eugene Hertz, Thimble is  growing the $250 billion business insurance market by making it more accessible: 75% of Thimble customers are first-time business insurance buyers. For that reason and so many more, Thimble has raised over $45 million in backing from IAC (NASDAQ: IAC) and other top venture capital firms.

For more information, visit


Our Values

Our unique culture is built around our six core 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.

Own Every Detail

Be ruthlessly precise. Disciplined. Sweat the small stuff.

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.

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.

About the Role

We are seeking an Underwriting/Compliance Analyst to support our Insurance Department. This person will work closely with our Executive Underwriter and Compliance Director.


Primary underwriting responsibilities to include the following:

  • Make recommendations for changes in underwriting guidelines and coverage applications to underwriting team based on data analysis of book performance
  • Maintenance of underwriting guidelines and coverage applications
  • Ensure broker/agent/customer sales representative adherence to underwriting guidelines and principles of Thimble
  • Underwriting referrals in accordance with Thimble standards
  • Assist claim adjusters with underwriting issues on claims where required
  • Assist in the underwriting and processing of cancellations, nonrenewals and renewals

Primary compliance responsibilities to include the following:

  • Compliance reviews of policy forms for new and existing products
  • Research and drafting of new forms
  • Maintain forms lists and usage for all products
  • Implement practices and processes to ensure compliance with state statutes and regulations
  • Coordinate with engineering team to ensure accuracy of form packages
  • Participate in audits by insurers, reinsurers and regulators
  • Act as a liaison between the various departments at Thimble (Product, Business Development, Marketing and Insurance)
  • Other duties as assigned.


  • Bachelor’s degree preferred but not required
  • 3-5 years of experience/knowledge of P&C insurance
  • Must demonstrate analytical skills and attention to detail
  • Familiar with ISO, SERFF, LexisNexis, SNL, APCIA, NAIC & DOI websites
  • Proficient in Google Suites
  • Proficient in MS office, specifically Word and Excel
  • Must be able to work well and respectfully with others, with minimal supervision and in a very fast-paced environment, subject to changing priorities
  • Ability to effectively manage multiple projects, prioritizing high impact ones
  • Exceptional written and oral communication skills
  • Creative problem solving, not problem identifying
What You’ll Do in 30 Days:
  • Get a warm welcome, meet the rest of the company, and get situated in your new position
  • Meet with the Team leads of the units you will be supporting
  • Gain a thorough understanding of our insurance product offerings and the different channels and ways that we sell coverage
  • Become familiar with the various software programs we use (Freshdesk, Freshchat, Looker, Whimsical, Asana, Stripe, KwikComply & more)
What You’ll Do in 60 Days:
  • Be completely comfortable with our suite of products and offerings
  • Identify areas of improvement to help shape product decisions throughout the company
  • Supporting the Executive Underwriter and Compliance Director
What You’ll Do in 90 Days:
  • Have complete ownership of your area of responsibility
  • Assist other members of the company with inquiries within your areas of responsibility
  • Full end to end product knowledge


Thimbler Benefits

  • Comprehensive health, vision, and dental coverage
  • 23 days paid vacation, 10 company-wide holidays, 1 VTO (Volunteer Time Off), and unlimited sick time
  • Parental Leave: 100% paid 12 weeks and 2 weeks gradual return
  • Ability to work remotely
  • Company computer hardware of your choice
  • Remote office/Work from home reimbursement
  • Monthly co-working space and/or child care reimbursement
  • Monthly wellness reimbursement & ClassPass monthly credit
  • Other health & wellness perks including One Medical, Teladoc, Talkspace, Kindbody, and Health Advocate
  • Early Fridays (no meetings after 3:00 pm EST) or Summer Fridays (out of office at 3:00 pm EST)
  • Weekly happy hours, trivia, and fun!
  • Competitive pay
  • Generous stock options

How to apply

Apple for (Commercial Insurance) Underwriting & Compliance Analyst Position Here!