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, 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 $24.3 billion in capital at March 31, 2025. 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.

ABOUT THE ROLE

We are hiring a VP of Product to help lead our Product Team. This is an exciting opportunity to develop and execute on our roadmap of new launches and enhancements, aimed at building a best-in-class insurance experience. Reporting to the President, this role will be critical in ensuring that Thimble becomes the one-stop-shop for all small business insurance needs.
Our Product team owns both day-to-day execution of product deliverables as well as strategic thinking about the future roadmap. We are looking for a leader to inspire and mentor team members as well as negotiate and manage conflicting priorities and expectations across our other departments. It is essential that this person has a sense of the tradeoffs required when making product decisions and is comfortable moving quickly and independently when data is ambiguous.
The right person for this role will be a resourceful self-starter who can deliver on objectives with little oversight and be comfortable telling competing stakeholders “No” when warranted. Success in this role will be measured by the ability to deliver projects that make a meaningful, measurable difference to Thimble’s objectives.

WHAT YOU’LL DO

• Work with Thimble Leadership to create a roadmap that aligns our product with our OKR’s
• Directly manage a team of senior product managers and designers
• Deliver frontend, backend, and structural enhancements that grow our business
• Provide post-launch analytics of the health of the product
• Work hand in hand with engineering to manage the Sprint process
• Work closely with internal and external stakeholders to ensure that their needs are met
• Leverage data to continuously improve existing features and functionality
• Launch entire new lines of business / insurance

WHAT YOU’LL DO IN 30 DAYS

• Learn how Thimble works from industry and technical perspectives - inside and out
• Become comfortable with the Thimble platform
• Get to know your team and understand their skills and challenges
• Meet with Thimble’s department heads and understand their needs
• Get familiar with Thimble’s OKR’s and the current roadmap

WHAT YOU’LL DO IN 60 DAYS

• Finalize a roadmap for the remainder of 2025. Balance strategic long-term projects with more tactical tweaks and bug fixes
• Work with engineering to optimize the current software development process
• Establish a cadence of meetings to ensure business owners’ concerns are being heard
• Plan the 2026 roadmap

WHAT YOU’LL DO IN 90 DAYS

• Deliver on multiple sprints
• Show the ability to adjust the roadmap due to an ever-changing environment
• Determine a plan for optimizing the usage of overseas resources
• Create reporting on the health of the product
• Create metrics on the performance of the product and engineering teams