Enablement Program Manager

Enablement Program Manager

About Cornerstone

At Cornerstone, we believe in AI that works in the service of people, amplifying their judgment to drive high-performing, future-ready organizations forward. Cornerstone Workforce AI™, the intelligence platform for workforce readiness, brings together workforce and labor market data into a proprietary Cornerstone People Graph™, translating signals into intelligence, targeting learning where it matters, developing critical skills, and surfacing hidden talent. Delivered as an open, enterprise platform across whatever application your people work in every day, Cornerstone Workforce AI is built for scale, security, and trust, with certified AI guardrails. As an industry leader, Cornerstone is helping approximately 7,000 organizations, 140M+ users, across 186 countries build continuous workforce readiness.

About the Role

The Customer Enablement Program Manager is responsible for the planning, execution, and successful evaluation of major customer enablement initiatives tied to Cornerstone OnDemand priorities. The Program Manager will ensure that enablement initiatives are well defined with measurable outcomes that link to bottom line impact including product adoption and expansion and customer renewals. The program manager will coordinate SME and stakeholder sessions, track and manage project documentation, maintain project files to ensure version control, identify program/project risks and mitigation approaches, and provide regular program/project status updates.

Key Responsibilities

· Lead the planning and execution of strategic customer enablement programs, ensuring timely delivery and adherence to defined quality standards.

· Develop and maintain program / project documentation, including project charters, workplans, risk mitigation plans, and change logs.

· Establish and manage feedback channels to capture, organize, and synthesize customer needs, insights, and opportunities for improvement.

· Facilitate stakeholder, SME, and team sprint meetings, document decisions, coordinate follow-up, and drive action-item completion.

· Leverage AI tools to streamline program management, synthesize stakeholder and customer feedback, and generate actionable insights, applying additional reviews to validate accuracy and relevance.

· Monitor progress against milestones, proactively address risks and dependencies, and deliver audience-appropriate status reports highlighting progress, issues, and required decisions.

What Success Looks Like

Use 3–5 measurable targets appropriate to the role. Set baselines, timeframe, and ownership; distinguish directly owned operational metrics from influenced outcomes.

· Ability to manage programs and projects to on-time completion with deliverables that achieve pre-determined quality standards consistent with a high-touch customer experience.

· Ability to directly influence metrics such as customer engagement with learning solutions, product adoption, and net promoter score.

· Tracks time and process gains and efficiencies utilizing AI-driven tools and solutions.

Required Experience

· 5 or more years in a SaaS program management role with focus on AI solutions.

· Agile project management certifications include PMI ACP, Certified ScrumMaster (CSM).

· Direct or indirect leadership of cross-functional teams focused on customer enablement solutions.

· Expertise in using AI-powered project management software including, but not limited to, Asana.

· Experience in using cloud-based communications software such as Slack and MS Teams.

Preferred Experience

· Additional certifications as a Professional Scrum Master (PSM I), Certified Scrum Product Owner (CSPO), etc.

· Experience teaching or coaching others agile program and project management techniques.

· Experience working with internal go-to-market and implementation teams as well as external partner organizations.

AI & Continuous Learning

· Uses AI tools every day in their own work and can show an example where AI changed how the work is done, not just how fast.

· Evaluates AI output critically for accuracy, bias, privacy and data handling, and knows when a human must decide.

· Actively explores internal (Cornerstone AI) and external tools, brings recommendations to the team, and retires tools and processes that do not earn their place.

· Keeps skills current through communities, certifications, hands-on experimentation and industry learning, and shares what they learn with the team.

How You Work

· Customer obsessed: Start with the learner’s and the account’s problem, not the tool.

· Innovate and transform: Challenge the status quo and retire systems and processes that do not earn their place.

· Proactive leadership: See problems and act before being asked.

· Get it done: Ship, measure and iterate.

· Forward looking: Plan for where technology and the business are going.

· AI native: Use AI daily to rethink work, not just accelerate it.

· Get uncomfortable to succeed: Take on hard, ambiguous problems and stay with them.

Our Growing Presence in Costa Rica

Cornerstone is excited to be building a new hub in Costa Rica as part of our continued investment in growing our global talent and capabilities. We are bringing together teams across a variety of functions, creating exciting opportunities for people to join us at the ground floor of this new chapter and help shape how we grow in the region.

We have invested in a new office in Costa Rica, with construction beginning soon, and we expect our presence and capabilities in the region to continue expanding over time. For those joining us now, this is a unique opportunity to help build something from the beginning, work alongside talented colleagues across Cornerstone globally, and be part of our longer-term growth in Costa Rica.

Employment Structure

As we establish our operations in Costa Rica and complete the process to operate under the country’s Free Trade Zone Regime, Cornerstone is partnering with Recluta, our local Employer of Record (EOR).

Our Culture

Spark Greatness. Shatter Boundaries. Share Success. Are you ready? Because here, right now – is where the future of work is happening. Where curious disruptors and change innovators like you are helping communities and customers enable everyone – anywhere – to learn, grow and advance. To be better tomorrow than they are today.

Who We Are:

At Cornerstone, we believe in AI that works in the service of people, amplifying their judgment to drive high-performing, future-ready organizations forward. Cornerstone Workforce AI™, the intelligence platform for workforce readiness, brings together workforce and labor market data into a proprietary Cornerstone People Graph™, translating signals into intelligence, targeting learning where it matters, developing critical skills, and surfacing hidden talent. Delivered as an open, enterprise platform across whatever application your people work in every day, Cornerstone Workforce AI is built for scale, security, and trust, with certified AI guardrails. As an industry leader, Cornerstone is helping approximately 7,000 organizations, 140M+ users, across 186 countries build continuous workforce readiness.

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