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Salary: USD 140,000 - 220,000 / annual
WithCoverage is redefining insurance and risk management by replacing traditional brokerages with AI-supercharged technology. The company partners with high-growth brands including GoPuff, Eight Sleep, Bombas, and others across consumer, hospitality, manufacturing, and defense sectors. Founded by JD Ross (co-founder of Opendoor) and Max Brenner (Bain, Compound), WithCoverage has raised over $50M from Sequoia, 8VC, Khosla Ventures, and Crystal Venture Partners.
As a Product Manager on the R&D team, you will turn complex operational workflows into simple, effective products. You'll work directly with teams across the business to understand workflows, identify bottlenecks, and translate them into product and automation improvements. Your responsibilities include:
• Turning operational pain into product by working with cross-functional teams to identify where software and AI can create leverage
• Scoping problems clearly with explicit requirements, acceptance criteria, edge cases, and success measures
• Driving products from problem to production, owning execution across design and engineering
• Building AI-native products using modern AI tools as part of your day-to-day work
• Measuring what you build by defining success metrics before development and using data to iterate
• Developing scalable product practices that maintain speed while introducing stronger product discipline
• Making good tradeoffs between user needs, implementation complexity, speed, and impact
You'll also help mature the company's product development processes as it scales from a scrappy early environment toward stronger product discipline around scoping, measurement, prioritization, and iteration.
REQUIREMENTS:
• 2+ years of product management experience and likely 5+ years of total professional experience
• Exceptional structured thinking: ability to turn complicated, ambiguous workflows into clear problem statements and concrete acceptance criteria
• Strong core product management skills: scoping, prioritization, tradeoff analysis, writing clear requirements, and driving cross-functional execution
• High data fluency: naturally ask how success will be measured, define metrics as part of product development, and use evidence to decide on investment
• Experience building products for complex workflows, ideally in B2B software, internal tools, operations-heavy environments, or similar domains
• AI-native work approach: use AI to move faster, understand technical systems, prototype ideas, and reduce distance between concept and usable product
VALUED EXPERIENCE (not required):
• Operations or BizOps background transitioning to Product
• Early-stage PM experience at scaled technology companies
• Consulting background with structured problem-solving skills
NOT REQUIRED:
• Insurance domain expertise (will develop quickly on the job)
• Traditional technical/software engineering background (comfort with technical systems and working with engineers is sufficient)
• Experience finding entirely new product categories (role focuses on executing well against known, high-value problems)
