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Head of Broker Distribution



United States
Posted on Wednesday, October 18, 2023
About Us
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 entrepreneurs Jay Bregman and Eugene Hertz, 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 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.
Thimble is seeking a Head of Broker Distribution to develop, execute, and own the strategy to drive large growth (>$250M annual premium) via our Broker Distribution channels. This highly versatile, well-connected individual will help be the mastermind of Thimble’s broker distribution strategy. The candidate should have extensive experience cultivating growth from existing brokers agents, as well as experience sourcing and signing relationships with the largest insurance carriers, brokerages, and wholesale partners in the country. The ideal candidate will also be comfortable with underwriting guidelines in small commercial insurance as this person will work closely with Thimble’s Insurance product development team to launch new insurance products with clear value propositions and compelling incentive structures for accelerated distribution through partnership channels.
The Head of Broker Distribution will report directly to Thimble’s Chief Revenue Officer and join our talented group to be a key member of our team. This role's primary objective is to drive new customer acquisition through the broker channels, including independent agents, wholesalers, aggregators, commercial rating platforms, insurance carriers, and affinity partners.


  • Own the entire broker distribution channel from end-to-end, including the Broker user experience from sign-up to sale, and ongoing engagement with our independent brokers, broker agencies & broker partners.
  • Work with our product and engineering teams to inform the prioritization and roadmap to build world-class broker tools including responsive web applications, apps, and customer management – the sky’s the limit!
  • Build and develop a team of A-player Broker Development Representatives and other roles as required to achieve explosive growth.
  • Source, negotiate, and sign partnerships with insurance carriers and intermediaries to distribute Thimble’s business insurance product.
  • Develop the Broker marketing & communications strategy and execute on programs designed to effectively launch of new products & features to grow broker activations.
  • Build out new product & broker features to drive growth through close partnership with Insurance, Product, etc. with an eye on massive distribution opportunities both inside and outside of traditional insurance channels.
  • Create new distribution opportunities by tailoring Thimble’s Widget/API offerings; leverage Thimble’s integration capabilities and work with Product to embed insurance in partner user experiences.
  • Own external distribution and industry relationships; leverage these relationships for industry knowledge, competitive intelligence, and long-term strategic partnership opportunities.
  • Develop and nurture a Thimble brand which brokers see as providing the best technology and user experience for their needs in the market, by a long shot.
  • Contribute to Thimble’s overall strategic direction by taking an active role in meetings and being a key participant in annual and quarterly planning sessions.
  • Be a teammate, mentor, coach, and lead the existing and new team members to achieve objectives and exceed targets.

Projects You'll Work On

  • Full accountability and oversight for the P&L of our intermediated distribution.
  • Broker Distribution: Own the growth targets & strategy for acquiring and engaging brokers to make Thimble their go-to small business insurance solution.
  • Carrier Partnership Distribution: Create the playbook for partnering with large nationwide carriers; execute on these partnerships by working cross functionally with Marketing & Product and managing partnerships toward shared growth targets.
  • Affinity Partnerships: Develop the go-to market strategy for affinity partners; create user experiences that embed the Thimble offer at the point of intent to drive conversion and acquire new customers while reducing Thimble’s blended cost of acquisition.

What We're Looking For

  • 10+ years of go-to market enterprise partnerships, business development, and/or sales experience, ideally within the P&C insurance industry.
  • Strong relationships within the insurance industry, including with senior individuals at carriers, intermediaries, and regional/national agencies.
  • Excellent communication and presentation skills, including speaking in front of large audiences.
  • Highly-organized with ruthless attention to detail.
  • Executive presence.
  • Strong analytical ability and highly structured thinking skills.
  • Bachelor’s degree required.
  • P&C License or CPCU designation a plus.

What You’ll Do in 30 Days

  • Understand the current Thimble Broker Program and provide a gap analysis of areas for improvement with actionable feedback
  • Understand Thimble’s current Broker Business Development & Growth strategy and provide areas of improvement & a clear roadmap of projects to focus on in your first year.
  • Leverage your network to set up distribution partnership conversations.

What You’ll Do in 60 Days

  • Begin executing on the highest priority projects laid out for BD.
  • Make a recommendation for engaging brokers via enhanced marketing activities like direct mail, email marketing, account management, and compelling incentive structures.

What You’ll Do in 90 Days

  • Demonstrate ownership over all three BD channels - Brokers, Carriers, and Affinity partners.
  • Deliver a tactical plan for growing the Broker Program, including the user experience and new customer acquisition forecasts / expenditures required to meet goals.
  • Negotiate and sign partnerships with leading national carriers, brokerages, and insurance intermediaries to distribute Thimble’s product.
Thimbler Benefits & Perks
-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!