Senior Director - AI Enablement

Greystar Management Services•Carolina, SC

4d•Remote

About The Position

The Senior Director, AI Enablement owns the production of role-specific AI capabilities, including skills, projects, agents, product education, and workflows that enable Greystar teams to use GPS, Prism, and the data platform in their work. The role focuses on practical artifacts and tools that employees can use with real Greystar data, and on measurable changes in how they work. Training is a delivery mechanism rather than the product. This role is the technical counterpart to the Director, Talent Development in People & Culture. People & Culture owns the enterprise learning framework, leadership development, learning technology, and workforce distribution channels; the Senior Director owns the technical content, artifacts, standards, and adoption outcomes. The role requires hands-on fluency with AI tools and data platforms, as well as the commercial judgment to connect workflow improvements to business value. The position leads the AI Enablement team’s shift from a training orientation to a build orientation. It defines role-based capabilities, creates and governs AI artifacts, measures adoption and outcomes, partners with People & Culture and technical teams, and establishes standards for safe, governed use. The position may be performed remotely anywhere in the United States except Alaska.

Requirements

Experience leading an AI or technology enablement function in a large, complex organization through an actual adoption curve, rather than only a pilot program.
Demonstrated hands-on experience building production LLM tooling, such as skills, prompt systems, or agent workflows, that other people used at scale.
Experience partnering closely with data or engineering teams to ground enablement in real systems and data, and with HR or L&D as a distribution partner.
Ability to measure adoption and outcomes rigorously and distinguish reach, adoption, and impact.
Comfort with Claude Enterprise or API, MCP, prompt and skill design, and reading a data model.
Ability to build a working skill against a governed dataset without an engineer.
Ability to connect enablement artifacts to a P&L measure such as NOI, hours, or CAC.
Product discipline in treating skills as versioned, owned, tested artifacts with users rather than course materials.
Strong influence across functions and levels, with the ability to maintain boundaries with HR and the business without creating friction.
Clear, concise communication with a senior founder-led audience and candor about what is not working.
Comfort with ambiguity, creating structure where none exists, and abandoning it when it stops working.

Nice To Haves

Experience in operations-heavy, distributed businesses such as real estate, financial services, healthcare, or logistics; multifamily experience is not required.

Responsibilities

Define what AI-enabled work means for priority roles by identifying relevant decisions, reports, and repetitive workflow steps, and build or coordinate the artifacts and education that support those roles.
Author and ship Skills, projects, and agent workflows grounded in Greystar metric definitions (Atlas), the data platform (DMP), and intelligence products (GPS, Prism, LEAP); build initial versions personally and scale the team’s output.
Maintain a governed skills and tools library with ownership, versioning, test cases, and deprecation processes.
Sequence work according to leverage, prioritizing key roles in coordination with leadership, the GPS roadmap, and FDI Pod deployments.
Own AI capability adoption metrics across eligible roles, including active users, repeat usage, workflow coverage, and time-to-first-value.
Instrument enablement artifacts so usage is visible without self-reporting and partner with Data Engineering on consumption and usage feeds.
Collect field feedback on what breaks, is ignored, or is copied, and iterate on artifacts weekly.
Report adoption alongside FDI Pod impact so costs and value are shown together.
Serve as the primary technical partner to the Director, Talent Development and People Strategy & Programs on AI readiness.
Feed enablement artifacts and technical curriculum into Workday Learning and People & Culture programs rather than building a parallel LMS.
Share role-level adoption data with People Strategy & Programs to help target manager enablement and communications where readiness lags.
Jointly define AI-ready role profiles for hiring and internal mobility, with People & Culture owning the competency framework.
Set technical standards for enablement artifacts, aligning data access with the External Data Sharing Framework and Unity Catalog permissions and preventing ungoverned data paths.
Ensure skills use Atlas/GPS as the definition of record and that platform numbers take precedence when skills and legacy reports disagree.
Partner with InfoSec on prompt, data, and model-flexibility standards as the model landscape changes.
Lead and retool the AI Enablement team toward building, hiring for skill authorship and applied AI over instructional design where they conflict.
Build a business-unit champion network with clear standards for what champions may and may not ship.
Model a narrow-aperture operating approach: ship, measure, and iterate, and decline requests that lack a role, workflow, and metric.

Benefits

Competitive medical, dental, vision, disability, and life insurance benefits.
Low-cost (free basic) employee medical coverage for employee-only coverage.
Paid time off, including 15 vacation days, 4 personal days, 10 sick days, and 11 paid holidays for new hires; additional vacation accrues with tenure.
Birthday off after one year of service.
Onsite housing discount at Greystar-managed communities for onsite team members, subject to discount and unit availability.
Six-week paid sabbatical after 10 years of service and every five years thereafter.
401(k) with company match up to 6% of pay after six months of service.
Paid parental leave.
Lifetime fertility benefit reimbursement up to $10,000, including adoption or surrogacy.
Employee Assistance Program.
Critical illness, accident, hospital indemnity, pet insurance, and legal plans.
Charitable giving program and benefits.
May be eligible for a quarterly or annual bonus program based on individual and company performance.