Job description
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.
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 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 We’re Looking For
- 10+ years of product experience in an environment where features and improvements were constantly shipped
- Experience working in either insurtech/insurance, or working in a highly regulated field where requirements are often restricted by regulation is highly preferred
- Skilled in managing a team, including but not limited to, PMs and designers
- Experience working closely with both onshore and offshore engineers in an Agile environment
- Proven success negotiating requirements and project milestones with peers and executive leadership team members in a confident and compelling manner
- Comfort and resourcefulness with data – experience in assessing which data points are needed for the health and quality of your products and how to go about getting the data you don’t have
- Working knowledge of building consumer products and backend tools in both native app and web environments (experience with Flutter development preferred)
- Proven experience shipping features or whole products that had a material, positive impact on a business
- Startup experience strongly preferred; entrepreneurial spirit is a must
- Thick skin – you’re comfortable taking criticism and you’re not afraid to double down on your arguments when the data supports them
What Success Looks Like
- Creating and execution of a roadmap that aligns with the company goals and maximizes output given bandwidth constraints, showing flexibility to adapt to an ever-changing, dynamic environment
- Meet OKR’s for LTV, new user growth, retention, and compliance
- Demonstrate the ability to work closely with engineering, both US based and overseas
- Support our insurance, marketing, broker, customer service, and business development teams, working with designers and engineers to create and implement solutions that give partner teams the autonomy and tools required to enable their success
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
Thimbler Benefits & Perks!
-Fully remote company
-Thimble Fridays! (out of office at 12:00pm local time)
-Comprehensive health, vision, and dental coverage
-401(k) auto enrollment and matching (100% of the first 3% and 50% of the next 3%)
-PTO: 20 days vacation + 8 floating days + 10 company-wide holidays + 1 VTO (Volunteer Time Off) + unlimited sick time
-Parental Leave: 100% paid 12 weeks + 2 weeks gradual return
-Computer choice of Mac or PC
-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!
