Director of Underwriting (Small Commercial Insurance - All Lines)

Thimble is a leading insurtech platform for small business customers and agents. Thimble allows customers to quickly get insurance coverage by the job, month or year using its award-winning app, website, or over the phone.

Founded by serial entrepreneur Jay Bregman, Thimble works with a variety of carriers to bring the best insurance solutions to small businesses, brokers and agents. Since it was founded, Thimble has delivered more than 170,000 policies to small businesses across the United States.

Thimble was acquired by Arch Insurance, a unit of Arch Capital Group Ltd. (Nasdaq: ACGL), a publicly listed Bermuda exempted company with approximately $15.6 billion in capital at Dec. 31, 2022. Arch, which is part of the S&P 500 Index, provides insurance, reinsurance and mortgage insurance on a worldwide basis through its wholly owned subsidiaries.

Thimble's innovative culture and technical expertise are an incredible addition to Arch Capital’s portfolio of offerings. The acquisition expands Arch’s suite of digital solutions for small business customers and brokers. Thimble will remain a separate subsidiary, working closely with the Arch Group team. 

For more information, visit thimble.com.

Our unique culture is built around our six core values:

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.

Act. Move forward. Learn. You can only make a decision based on the best information you have – so make it.

Be ruthlessly precise. Disciplined. Sweat the small stuff.

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.

Show up early and ready. Deliver on time or before. Make the most of your time, so others can make the most of theirs.

Treat every person, and their ideas, with respect. Cherish diversity.

We are seeking a seasoned underwriter to be a player/coach and lead the underwriting operations of Thimble, the industry's compliant radicals, in the development of risk selection, implementation and offering of new products to a wider and more diverse customer base.  

Primary underwriting responsibilities for the Verifly Insurance Services, LLC dba Thimble Insurance Services, a general agency, to include the following:

-Ongoing development, revision, implementation, and maintenance of underwriting guidelines and coverage applications   

-Ensure 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 development of initial filings for new products and filing updates for mature products that do the following:   

-Contain meaningfully unique features perceived highly valuable by our customer groups  

-Allow Thimble to grow significantly in the SMB market   

-Solve the basic insurance needs of our customer groups   

-Produce an acceptable underwriting profit  

-Monitor and manage Thimble's underwriting risk to deliver target loss ratio while supporting Thimble's mission and strategy

-Identify necessary underwriting changes   

What We're Looking For

• 10+ years of small commercial insurance experience in P&C underwriting, with the ability to still be hands-on
• Proficiency in analyzing and making decisions on policies in a timely manner
• Ability to work well and respectfully with others, with minimal supervisions, and in a very fast-paced environment   
• Experience managing multiple projects, prioritizing high impact ones
• Ability to make decisions quickly and decisively
• Exceptional written and oral communication skills
• Microsoft Word and Excel proficiency  
• Creative problem solving skills
• Bachelor's Degree or equivalent experience

What You'll Do in 30 Days

• Understand Thimble's product set and roadmap
• Take ownership of Thimble's underwriting process
• Understand Thimble's content/SEO strategy and the Insurance team's role in it
• Understand Thimble's distribution strategy
• Digest company performance and customer data to date and training on Thimble's data infrastructure
• Review data dump including all team presentations, filings, PAA agreements, carrier presentations, and product documentation
• Understand Thimble's claims process
• Understand organization, strategic plan, and the insurance challenges
• Understand Carrier guidelines as they have been presented to us

What You'll Do in 60 Days

• Understand Thimble's financial model and the insurance impact
• Understand Thimble's Business Development strategy, including broker strategy and impact of Thimble's Business Development on insurance roadmap
• Assist in the development of additional commercial property and inland marine insurance products
• Assist in the development of insurance products for future growth

What You'll Do in 90 Days

• Contribute to assuring strategic projects and goals are on plan and suggest modifications, if required
• Contribute to assuring that the annual Strategic Plan is on target and completed
• Contribute to planning for investigation of new products for 2024-2025 and beyond 

-Fully remote company

-Thimble Fridays! (out of office at 12:00pm local time)

-Comprehensive health, vision, and dental coverage

-PTO: 20 days vacation, 8 floating days, 10 company-wide holidays, 1 VTO (Volunteer Time Off), and unlimited sick time

-Parental Leave: 100% paid 12 weeks + 2 weeks gradual return

-Company computer hardware of your choice

-Work from home setup reimbursement

-Monthly co-working space and/or child care reimbursement

-Monthly ClassPass credit

-Quarterly wellness reimbursement

-Other health & wellness perks including: One Medical, Teladoc, Talkspace, Kindbody, and Health Advocate

-Virtual events, happy hours, trivia, and fun!