Senior Product Manager

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 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 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 looking for an exceptional Product Manager to join our growing team of PMs to execute on an exciting roadmap of new product launches and key product experience improvements, aimed at delivering best-in-class experiences.  

Reporting to the SVP of Product, this role will lead Thimble’s key growth strategy - broker distribution. This means working closely with brokers, aggregators and platforms to enable Thimble to be easily accessible by brokers.  

This role will own both day to day execution of product deliverables as well as strategic thinking about the product roadmap. We are looking for a real leader – this role needs to be able to negotiate and manage competing priorities and expectations across our tech, insurance, data, customer service, business development, and marketing teams. Success for this candidate will be measured by their ability to deliver business impact.  

It is critical that this candidate is a resourceful self-starter who can deliver on objectives with little oversight. It is also critical that this candidate have excellent project management skills, and is able to effectively break a product launch down into its component pieces. 

• Own the broker experience strategy, roadmap, objectives, metrics and outcomes 
• Lead the broker experience squad 
• Lead partnership conversations 
• QA features and product launches to ensure quality across all platforms (iOS, Android, Web, Mobile Web) 
• Own the feedback loop between brokers, customers, partners and engineering 
• Leverage data to continuously improve existing features and functionality 

• 3+ years of product experience in an environment where features and improvements were constantly shipped. Preferred experience working in a highly regulated field where requirements are often restricted by regulation 
• Skilled in a B2B SaaS environment, working with APIs 
• 3rd party integration and experience with managing 3rd parties 
• Comfort and resourcefulness with data – you’re able to assess which data points you need to assess the health and quality of your product, and how to go about getting the data you don’t have 
• Deep empathy for customers – you are the voice of the customer and need to relentlessly push for what is best for them, not just for the business 
• Working knowledge of building consumer products and backend tools in both native app and web environments 
• Obsessively detail-oriented, but able to step away from the details to focus on the big picture 
• The ability to negotiate requirements and project milestones with peers and management in a confident and compelling manner 
• 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

• Deliver impact - meet OKRs and other business objectives 
• Deliver written documents - strategy docs, roadmaps, PRDs, tickets, business impact assessments, etc. 
• Deliver verbal presentations – to executive team, at company all hands, to stakeholders, to partners 
• Deliver initiatives – large and small from your roadmap 

• Get to know the rest of the team including your squad and stakeholders 
• Learn how insurance works from industry and technical perspective, inside and out 
• Learn how Thimble’s product works  
• Learn how your area of Thimble’s product works 
• Learn the current strategy, roadmap, objectives and metrics for your product area. 
• Get up to speed and ensure delivery of in-flight initiatives 

• Lead team meetings 
• Propose changes to strategy, roadmap, objectives and metrics for your product area

• Fully own the strategy, roadmap, objectives, metrics and outcomes for your product area

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!