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Cornerstone is seeking a Director of Product Management to lead a core area of its Learning product line. This is a senior product leadership role combining product vision and strategy, people leadership, and disciplined execution.
You will own the strategy and roadmap for your product area, lead and grow a team of product managers, and be accountable for delivering learning experiences that drive measurable adoption, learner and administrator value, and commercial impact. You will partner across engineering, design, data science, content, customer success, services, sales, and marketing to move capabilities from customer need through discovery, launch, adoption, and outcome realization.
Key responsibilities include:
**Set Vision & Strategy:** Own the product vision and multi-year roadmap for your Learning portfolio area, grounded in market trends, customer needs, and Cornerstone's strategy. Make and defend prioritization decisions with clear rationale, translating strategy into a sequenced roadmap and well-formed bets. Frame the business case for major investments—market sizing, opportunity, and expected outcomes—and align leadership and cross-functional partners. Champion AI and skills-based innovation where it creates real learner and administrator value.
**Lead & Grow the Team:** Hire, coach, and develop a team of product managers, setting a high bar for product craft, customer empathy, and accountability. Establish product standards and operating cadences for discovery, planning, release, and outcome review. Create clarity and alignment across product, engineering, and design leadership, and represent your area to executives and customers.
**Discover, Experiment & Measure:** Drive rigorous customer discovery, engaging directly with enterprise customers, learners, and administrators to validate problems and use cases. Run a hypothesis-driven practice—define success metrics, instrument products, and use experimentation and A/B testing to learn quickly and de-risk decisions. Define and own the success metrics and North Star for your area (adoption, engagement, retention, time-to-value, and business outcomes).
**Deliver with Rigor:** Drive cross-functional delivery across product, engineering, design, data science, content, customer success, services, and go-to-market teams. Establish strong operating cadences for milestone reviews, dependency management, risk tracking, and outcome measurement. Partner with go-to-market and customer-facing teams on rollout planning, launch enablement, implementation readiness, and feedback loops. Ensure capabilities are scalable, secure, compliant, and practical for adoption in enterprise environments.
Success is measured by a clear, well-communicated vision and roadmap that leadership, customers, and the team understand and rally behind; a high-performing product team that ships quality work on a predictable cadence; products that customers adopt and love; decisions grounded in evidence from discovery, experimentation, and metrics; and AI-assisted and skills-based capabilities launched in ways that are trusted, usable, and outcome-oriented.
**Requirements:**
- 10+ years in product management, including experience leading product managers, in enterprise software, SaaS, or platform organizations
- Track record of owning product vision and strategy for a product area and translating it into roadmaps that ship and drive outcomes
- Demonstrated people leadership—hiring, coaching, and growing product managers and setting team standards
- Strong discovery and experimentation skills: customer research, hypothesis-driven development, metrics definition, and A/B testing
- Proven ability to lead execution across complex cross-functional organizations with operational rigor and release discipline
- Excellent collaboration and communication skills across engineering, UX, data science, services, sales, support, and customer success, up to the executive level
- Experience delivering products in secure, enterprise-grade environments where trust, reliability, and scalability matter, including familiarity with security, privacy, and data governance
**Nice to Have:**
- Experience in learning, HR technology, talent management, or skills/EdTech domains
- Experience delivering AI-native products, intelligent agents, copilots, automation, or workflow-based AI in enterprise settings
- Experience with skills-based capabilities, content ecosystems, or analytics/insights products
- Familiarity with regulated, security-conscious, or compliance-driven product environments and enterprise governance models for AI and data
