Director, Product Management

About the Role

AI is transforming every industry, but enterprise customers need solutions they can trust.

As Director of Product Management, you'll lead the development and growth of Pearl's Enterprise AI business, creating products that combine advanced AI with human expertise to deliver reliable outcomes for enterprise customers.
You'll own the business strategy, product direction, and execution for this initiative, partnering closely with customers to validate new ideas, launch innovative offerings, and scale a growing business. This role is ideal for someone who has successfully built 0-to-1 enterprise products and wants the opportunity to own a business, not just a roadmap.

What You’ll Do

• Own the business end-to-end. You are the single accountable owner for Pearl's enterprise business. You'll define the vision, strategy, and goals, and lead a lean cross-functional team through execution and delivery.
• Deliver enterprise customer outcomes. Partner closely with enterprise customers and prospects to maximize product-market fit, unit economics, and scalability, translating a deep understanding of customer problems into differentiated, market-ready solutions.
• Define the go-to-market strategy. Partner with Business Development to shape the go-to-market strategy, value proposition, competitive positioning, pricing, packaging, and business model.
• Build and scale enterprise offerings. Define and productize Pearl's AI + Human offerings, determining how they're packaged, delivered, measured, and continuously improved.
• Establish the category standard. Help define what trustworthy, high-quality AI solutions look like for enterprise customers by setting the standard for human-in-the-loop AI, expert data, and enterprise-grade performance.
• Stay close to execution. While you'll set the strategy, you'll also operate as the team's lead Product Manager, working closely with Engineering, Design, Project Management, and GTM partners to ship products, solve customer problems, and drive measurable business outcomes.
• Lead cross-functional execution. Partner with leaders across Pearl, including the executive team, Brand Marketing, Machine Learning, Expert Operations, Analytics, and Legal, to secure alignment, remove obstacles, and ensure the business has the resources it needs to succeed.

What We’re Looking For

• A proven 0-to-1 builder. You've led the launch of new products, services, or business lines from concept through customer adoption and meaningful revenue.
• Enterprise B2B experience. You've built, launched, or scaled products for Fortune 500 companies or similarly complex enterprise customers. Experience owning a product line, business, or P&L is strongly preferred.
• A business builder. You're excited by the opportunity to own a business, not just a roadmap. You naturally connect customer needs, product strategy, go-to-market, and commercial outcomes into a cohesive plan.
• Lean startup fluency. You know how to identify the riskiest assumptions, run focused experiments, learn quickly, and determine when to invest, iterate, or pivot.
• Ability to turn ambiguity into execution. You translate ambiguous customer problems, market signals, and early research into clear product strategy, structured workflows, and production-ready delivery plans.
• Strong operational judgment. You know what it takes to build quality, trust, and repeatability while moving quickly in a fast-paced environment.
• Hands-on operator. You're comfortable moving seamlessly between business strategy and product execution. Prior experience as an individual contributor Product Manager is required.
• Low-ego, high-ownership leader. You're adaptable, data-driven, customer-obsessed, collaborative, and willing to roll up your sleeves to help the team succeed.

Nice-to-Haves

• Hands-on experience building AI-enabled products, including prompt engineering, AI evaluations, agent workflows, or similar technologies.
• Previous experience as a founder, venture studio leader, innovation lab leader, or general manager.
• Experience in frontier AI, enterprise SaaS, insurance, legal technology, veterinary, or automotive industries.
• Experience productizing expert networks, human data services, AI evaluation products, or data-labeling services.

What You're Not

• A pure strategist. If your last three roles ended with a recommendation deck instead of a shipped product, this isn't the role for you. We build, launch, and iterate.
• A leader looking for organizational scale. You will lead ~14 people, not 140. This is a lean, entrepreneurial business. You'll lead through ownership, influence, and execution, not by managing a large organization.
• An AI tourist. You've built with AI, not just talked about it. You have practical opinions about evaluations, hallucinations, and human-in-the-loop systems that come from shipping real products.
• A specialist who wants to stay narrow. This role spans sales, product, and engineering on the same day. If you prefer one lane, this will frustrate you.

Remote From these States: California, Florida, Georgia, Idaho, Illinois, Massachusetts, Michigan, New Jersey, New York, North Carolina, Ohio, Oregon, Pennsylvania, Texas, Virginia, Washington, and Wisconsin.

Pay Transparency: Pearl will provide pay transparency information upon application to those in qualifying jurisdictions. (Employment is with JustAnswer LLC, a Pearl company.)