Director, Product Management

About Pearl

Pearl leverages advanced artificial intelligence combined with verified human expertise to provide reliable and efficient professional services worldwide. Since 2003, the company has connected millions with licensed professionals across 196 countries, enabling easy access to expert help anytime and anywhere.

Core Values

• Data-driven decision-making prioritizing facts over egos
• Bold innovation through risk-taking and challenging norms
• Continuous learning and adaptation to foster creativity
• Customer-focused lean methodologies emphasizing rapid testing
• Humble mindset acknowledging past achievements don't guarantee future success

Role Overview

As Director of Product Management, you will lead the development and scaling of Pearl’s Enterprise AI offerings, driving products that unite cutting-edge AI technology with human insight to deliver trusted and dependable solutions for enterprise clients. This leadership role encompasses full business ownership, including strategy, product execution, customer engagement, and team collaboration to build and expand Pearl’s enterprise product portfolio.

Key Responsibilities

• Serve as the accountable owner for the enterprise business, crafting vision, strategy, goals, and guiding a cross-functional lean team through product delivery.
• Collaborate closely with enterprise customers to ensure product-market fit, sound economics, and scalability by translating customer challenges into innovative market-ready products.
• Develop go-to-market strategies in partnership with Business Development, shaping value propositions, competitive positioning, pricing, packaging, and business models.
• Design and scale AI plus human-expertise integrated offerings, managing packaging, delivery mechanisms, measurements, and continuous iterations.
• Define industry standards for trustworthy and high-quality AI solutions, focusing on human-in-the-loop AI, expert data, and enterprise-grade reliability.
• Remain hands-on in product leadership by working directly with Engineering, Design, Project Management, and Go-To-Market teams to deliver products and measurable results.
• Coordinate across departments—including executive leadership, Marketing, Machine Learning, Operations, Analytics, and Legal—to align priorities, overcome barriers, and allocate resources effectively.

Desired Qualifications

• Demonstrated experience launching new product lines or services from concept through adoption and revenue generation.
• Background building and scaling enterprise B2B products, preferably for Fortune 500 or equivalent companies, with ownership of product lines or P&L responsibility.
• A founder’s mindset—connecting customer needs with product and commercial strategies to own and grow a business rather than just a product roadmap.
• Proficiency in lean startup practices including hypothesis validation, rapid experimentation, and data-driven pivoting or investment decisions.
• Exceptional ability to translate ambiguous market signals into concrete strategies and execution plans.
• Strong operational judgment balancing quality, trust, repeatability, and speed in fast-moving environments.
• Experience as a hands-on Product Manager with a low-ego attitude and proactive leadership style, driven by data and customer obsession.

Preferred Additional Experience

• Practical experience developing AI-enabled products, such as prompt engineering or AI evaluation workflows.
• Leadership roles as a founder, venture studio innovator, general manager, or in innovation labs.
• Industry experience in frontier AI, enterprise SaaS, insurance, legal tech, veterinary, or automotive sectors.
• Expertise in commercializing expert networks, human data services, AI evaluation tools, or data-labeling platforms.

Who This Role Is Not For

• Individuals focused solely on strategy without proven product delivery experience.
• Leaders seeking large organizational management; this role involves leadership of roughly 14 staff.
• Those without practical AI product development experience.
• Specialists wanting narrow role focus, as this position integrates sales, product, and engineering responsibilities.

Work Location and Equity

This is a full-time remote opportunity available for residents in select U.S. states including California, Florida, Georgia, Idaho, Illinois, Massachusetts, Michigan, New Jersey, New York, North Carolina, Ohio, Oregon, Pennsylvania, Texas, Virginia, Washington, and Wisconsin.

Equal Employment Opportunity

Pearl embraces diversity and fosters an inclusive environment welcoming varied backgrounds and perspectives. The company is an equal opportunity employer and prohibits discrimination based on legally protected characteristics.

AI Hiring Disclosure

The hiring process may involve AI technology to capture and analyze interview responses. Applicants consent to this use by participating in the process.