Product Manager

WithCoverage replaces the traditional insurance brokerage with AI-supercharged risk management designed for the modern economy. We partner with hundreds of high-growth, category-defining companies, including GoPuff, Eight Sleep, Bombas, Chomps, and Blank Street Coffee. Our clients span iconic consumer brands, hospitality leaders, GCs, advanced manufacturers, and next-generation defense contractors. They operate in complex risk environments and need a partner that can move at their speed. Instead of a fragmented, manual brokerage stack, we have built a new category: elite risk advisors operating on top of proprietary technology. Our in-house Agency Management System gives our team and AI agents full visibility into policies, exposures, claims, billing, and commissions. This platform enables deep automation, better decisions, and a fundamentally higher standard of service. WithCoverage was founded by JD Ross (co-founder of Opendoor) and Max Brenner (Bain, Compound). We have raised over $50M from leading investors including Sequoia, 8VC, Khosla Ventures and Crystal Venture Partners. Our ambition is not to build a better brokerage. It is to redefine how risk is managed across the economy. Grow faster – We’re scaling quickly, giving you significant opportunities to learn, lead, and shape your career and the company's future. Work that matters – We protect the world’s most innovative brands: consumer icons, hospitality leaders, next-gen defense contractors, and US manufacturers. Redefine an industry – Insurance is one of the largest, slowest-moving markets. We rewrite the playbook with proprietary technology, automation, and AI. Financial rewards – We hire the best and invest in you. That means competitive comp, meaningful equity, and excellent benefits. We believe strongly in internal promotion and lay out a plan for everyone's career growth. About The Role: We are open to a wide range of levels for this role. As a Product Manager on our R&D team, you’ll turn complex operational workflows into simple, effective products. You’ll spend much of your time close to the people doing the work: sitting with teams, understanding where processes break down, identifying where software and AI can create leverage, and translating that understanding into clear product improvements. You’ll also help us mature how we build products as a company. We are moving from an early, highly scrappy environment toward a team that can maintain that speed while developing stronger product discipline around scoping, measurement, prioritization, and iteration. What You’ll Do: Turn operational pain into product. Work directly with teams across the business to understand complex workflows, identify bottlenecks and failure modes, and translate them into simple product and automation improvements. Scope problems clearly. Write clear product specifications with explicit requirements, acceptance criteria, edge cases, and measures of success. Break large problems into the smallest useful versions and know when additional complexity is no longer worth it. Drive products from problem to production. Own execution across design and engineering, resolve tradeoffs quickly, keep projects moving, and ensure what ships actually solves the underlying problem. Build AI-native products . Use modern AI tools as part of your day-to-day product work. Prototype ideas, explore workflows, interrogate technical systems, and push simple product changes yourself when that is the fastest path to learning. Measure what we build. Define success metrics before development begins, ensure products are instrumented to measure those outcomes, and use the resulting data to determine whether to iterate, expand, or move on. Develop scalable product practices. Help establish the product processes we will need as the company grows without introducing unnecessary bureaucracy. Bring strong opinions about what good product development looks like and adapt them to an environment that still values speed. Make good tradeoffs. Balance user needs, implementation complexity, speed, and expected impact. Know when to keep optimizing and when a product is good enough to move forward. Who You Are: You have 2+ years of product management experience and likely 5+ years of total professional experience. You are an exceptional structured thinker. You can take a complicated, ambiguous workflow and turn it into a clear problem statement, a tractable product scope, and concrete acceptance criteria. You have strong core product management skills: scoping, prioritization, tradeoff analysis, writing clear requirements, and driving cross-functional execution. You are highly data fluent. You naturally ask how success will be measured, define metrics as part of product development, and use evidence to decide whether to keep investing in a product. You have built products for complex workflows, ideally in B2B software, internal tools, operations-heavy environments, or other domains where understanding how people actually work matters more than designing a consumer interface. You are AI-native in how you work. You use AI to move faster, understand technical systems, prototype ideas, and reduce the distance between an idea and something usable. Experience We Value: We are open to a range of backgrounds, but some career paths are particularly relevant: Operations or BizOps → Product. You bring strong operational intuition, analytical rigor, and a natural focus on whether the product actually improves business outcomes. Early-stage PM → scaled technology company. You know how to move quickly and operate with limited structure, but you have also seen what strong product processes look like as a team grows. Consulting → Product. You bring structured problem solving, comfort with complex domains, strong communication, and experience turning ambiguous problems into clear recommendations. What Matters Less: Insurance experience. You do not need to arrive with deep insurance knowledge. You will develop domain expertise quickly by working directly with our team and customers. A traditional technical background. You should be comfortable understanding technical systems and working closely with engineers, but prior software engineering experience is not required. Finding entirely new product categories. This role is primarily focused on known, high-value problems and executing exceptionally well against them rather than searching for speculative new product bets. This role is on-site in our New York office. The expected cash compensation range for this position at the start of employment is $140,000–$220,000 a year . In addition, WithCoverage offers generous equity and equity refreshers. What We Offer: Competitive compensation that includes equity Comprehensive benefit plans for medical, dental, vision, life, and disability Pre-tax accounts (FSA, HSAs, dependent care FSAs, 401(k), commuter savings) Time Off: Flexible time off, sick leave, family and medical leave, major national holidays A curated in-office employee experience, designed to foster community, team connections, and innovation Collaborative, transparent, and fun culture #J-18808-Ljbffr WithCoverage