Director/Senior Director, Enablement & Community Digital Experiences - United States

Cornerstone onDemand • Chicago, IL • 1d ago

Director/Senior Director, Enablement & Community Digital Experiences

Cornerstone University · Customer & Partner Enablement

The mission

Cornerstone University exists to make enablement a driver of growth - accelerating customer adoption and retention, scaling partner readiness and revenue impact, and establishing education as a strategic growth function rather than a cost of doing business. This role owns how that vision is realized in the experience: the integrated digital environment through which partners, customers, and internal teams learn, certify, get unblocked, and get better at Cornerstone every day.

The Director/Senior Director, Enablement & Community Experiences is the architect and end-to-end owner of enablement's digital experience and community strategy. They define what world-class looks like across every surface including branded portals, AI conversational agents, in-the-flow-of-work guidance, mobile, and community, and turn it into one coherent journey per audience. They own the requirements and the roadmap, and they drive the platform, AI, and delivery agenda that brings it to life, partnering closely with IT, Product, and platform owners to build experiences that move business outcomes. This is the function's innovation and digital-experience leadership seat. The leader would be accountable for ensuring that the Cornerstone University feels and performs like the best in the market.

What this role owns

Integrated digital experience strategy and architecture. Own the target-state enablement experience as a single, coherent system across surfaces, partner and customer portals, in-the-flow-of-work delivery embedded where users actually do their jobs, AI concierge and agents, search, mobile, and community. Define the experience vision and the requirements behind it, maintain the prioritized roadmap, and serve as enablement's product owner across the experience and platform stack (Galaxy and adjacent systems), partnering with IT, Product, and platform partners to realize the vision and build against it.
AI-driven and agentic experiences. Lead the shift from static, one-size-fits-all enablement to intelligent, personalized, conversational delivery: AI concierge, learning and support agents, adaptive paths, in-@context guidance, and intelligent assessment. Set the standard for how AI shows up across partner, customer, and internal journeys, and drive these capabilities into production at scale rather than perpetual pilot. Leverage the Cornerstone products and other best of breen technologies to deliver best experiences.
Community as a scaled growth engine. Re-architect community from a support forum into a flywheel for adoption, advocacy, and peer enablement - champion and ambassador programs, expert co-creation, structured deflection, and partner activation - with every program explicitly wired to a business outcome rather than vanity engagement. Make community a connected part of the learning experience, not a parallel channel, so training, certification, community, and enablement operate as one journey.
Realizing the strategy and leading the innovation agenda. Translate the Cornerstone University vision and the function's commitments into delivered, measurable experiences across all three audiences. Bring a relentless outside-in lens, benchmarking against best-in-class enablement and community experiences, and run a disciplined pilot-to-scale motion that keeps the experience current and differentiating. Act as a thought leader internally and, where appropriate, externally for how Cornerstone enables its ecosystem.

Key leadership accountabilities

Set and own the multi-year digital experience and community strategy that realizes the Cornerstone University vision across partners, customers, and internal teams.

Own the prioritized experience-and-platform roadmap and the requirements behind it; establish and lead the governance interlock with Product, IT, Marketing/GTM, Services, Support, Alliances, and Customer Success so enablement's needs actively shape the platform agenda.

Define and stand up the AI concierge, agent, and personalization capabilities; set the bar for quality, intelligence, and measurement of the experience.

Lead the community transformation end-to-end, tying every program to named adoption, retention, certification, deflection, or partner-activation outcomes and owning the reporting on them.

Unify training, certification, community, and enablement into a single coherent journey per audience, delivered in the flow of work.

Partner with the Insights, AI & Platform Services function on instrumentation so experience and community performance is measured and continuously improved, and report impact in business terms to the VP and senior leadership.

What success looks like (first 12 months)

An agreed, multi-year experience strategy and roadmap partnering with product and IT and actively building against the vision, showcasing Cornerstone University as a best customer zero experience story.

At least one AI-driven experience (concierge, agent, or adaptive path) live in production and measurably improving time-to-value or self-serve resolution within first 6 months.

Community success reframed, instrumented, and demonstrably linked to adoption, certification, deflection, or partner activation.

A unified, in-the-flow-of-work journey shipped for at least one audience (customers), connecting training, certification, community, and enablement.

A credible, evidence-backed point of view on how Cornerstone University's experience compares to best-in-class , and a sequenced plan to close the gap.

What we're looking for

A strategic leader who has owned enablement, learning, or customer/partner experience at scale- and who thinks in business outcomes (adoption, NRR, time-to-value, partner readiness), not learning metrics.

Real digital-experience and platform fluency: someone who has designed or owned integrated enablement experiences across portals, in-the-flow-of-work delivery, and AI/agentic interfaces - not just consumed platforms others built.

A track record of bringing training, certification, enablement, and community together into a single experience.

Demonstrated ability to influence Product and IT roadmaps as the internal customer - defining requirements and driving cross-functional delivery for teams they don't manage.

Hands-on credibility with AI, personalization, and conversational/agentic experiences in a learning or CX @context.

A builder and an innovator with strong outside-in instincts and the operating discipline to scale pilots into production - comfortable leading in a lean, cost-conscious, transformation-mode environment.

Equal Employment Opportunity has been, and will continue to be, a fundamental commitment at Cornerstone OnDemand. All qualified applicants are given consideration regardless of race, color, gender, age, sexual orientation, national origin, marital status, citizenship status, disability, veteran status, or any other protected class as provided in applicable Federal, State, or Local fair employment laws. If you have a disability or special need that requires accommodation, please contact us at careers@csod.com

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