[Hiring] Senior Director - AI Enablement @Greystar

Role Description

The Senior Director, AI Enablement owns the production of role-specific AI capability: the Skills, projects, agents, product education and workflows that make GPS, Prism and our data platform usable inside the job, for the roles that matter most. Training is a delivery mechanism for this work, not the product. The product is a working set of content and tools a Greystar team member can pick up and use, on real Greystar data, and a measurable change in how they operate.

This is the technical counterpart to the Director, Talent Development in People & Culture. That role owns the enterprise learning framework, leadership development and the learning technology stack, and is the distribution channel to the workforce. This role owns what gets distributed — the artifacts, the technical standards behind them, and the adoption they drive.

This is a builder’s seat with a leader’s remit. The right person is fluent enough in Claude, ChatGPT, AI tools, MCP and data platforms to author skills personally and set the bar for a team that does, and commercial enough to argue, in NOI terms, why a given workflow should be rebuilt at all.

Key Responsibilities

• Role-Based Capability Production:
  • Define, for each priority role, what “AI-enabled” concretely means in the workflow — which decisions, which reports, which repetitive steps — and build the artifacts, or work with the teams to build the artifacts and education that deliver it.
  • Author and ship Skills, projects and agent workflows grounded in Greystar’s metric definitions (Atlas), data platform (DMP) and intelligence products (GPS, Prism, LEAP); personally build the first versions, then scale the team’s output working closely with your HR counterpart to expand delivery.
  • Maintain a governed skill & tool library with ownership, versioning, test cases and deprecation — treated as a product, not a training catalogue.
  • Sequence work by leverage: key roles first, in lockstep with leadership, the GPS roadmap and the FDI Pod deployments.
• Adoption and Measurement:
  • Own the adoption metric for AI capability across eligible roles: active users, repeat usage, workflow coverage, time-to-first-value.
  • Instrument enablement artifacts so usage is visible without self-report; partner with Data Engineering on the consumption and usage feeds.
  • Run the feedback loop from the field into the artifacts — what breaks, what is ignored, what gets copied — and iterate weekly.
  • Report adoption alongside FDI Pod impact so cost and value are always shown together.
• Partnership with People & Culture:
  • Serve as the primary technical partner to the Director, Talent Development, and to People Strategy & Programs on AI readiness; P&C owns the pathway, readiness approach and competency framework, and this role owns the technical content and the tools.
  • Feed enablement artifacts and technical curriculum into Workday Learning and P&C programs as the distribution channel; do not build a parallel LMS.
  • Share role-level adoption data (active users, workflow coverage, time-to-first-value) with People Strategy & Programs so manager enablement and communications can target where readiness lags.
  • Jointly define what an “AI-ready” role profile looks like for hiring and internal mobility, with P&C owning the competency framework.
• Standards, Safety and Governance:
  • Set the technical standards for enablement artifacts: data access aligned to the External Data Sharing Framework and Unity Catalog permissions; no ungoverned data paths.
  • Ensure every skill is grounded in the definition of record (Atlas/GPS); when a skill and a legacy report disagree, the platform number travels.
  • Partner with InfoSec on prompt, data and model-flexibility standards as the model landscape changes.
• Team Leadership:
  • Lead and retool the AI Enablement team from a training orientation to a build orientation; hire for skill authorship and applied AI over instructional design where the two conflict.
  • Build a champion network inside the business units that extends the team without adding headcount, with clear standards for what champions may and may not ship.
  • Model the operating principle of the function: narrow aperture, ship, measure, iterate; say no to requests without a role, a workflow and a metric attached.

Qualifications

• Led an AI or technology enablement function in a large, complex organization through an actual adoption curve — not a pilot program.
• Demonstrated hands-on record building with LLM tooling in production: skills, prompt systems, agent workflows or equivalent that other people used at scale.
• Partnered closely with data or engineering teams to ground enablement in real systems and real data, and with HR or L&D as the distribution partner.
• Measured adoption and outcomes rigorously and can distinguish reach, adoption and impact without prompting.
• Experience in operations-heavy, distributed businesses (real estate, financial services, healthcare, logistics) is an advantage; multifamily is not required.

Skills and Capabilities

• Technically credible: comfortable in Claude Enterprise / API, MCP, prompt and skill design, and reading a data model. Can build a working skill against a governed dataset without an engineer.
• Commercially literal: connects an enablement artifact to a line in the P&L (NOI, hours, CAC) or does not build it.
• Product discipline: treats skills as versioned, owned, tested artifacts with users, not as course materials.
• Strong influencing across functions and levels; holds a boundary with HR and the business without creating friction.
• Clear, concise communicator to a senior founder-led audience; candid about what is not working.
• Comfortable in ambiguity, building structure where none exists, and abandoning it when it stops working.

Compensation

• The salary range for this position is $180,000 - $200,000 USD Annually.
• Many factors go into determining employee pay within the posted range including business requirements, prior experience, current skills and geographical location.
• In addition to the base salary, this role may be eligible to participate in a quarterly or annual bonus program based on individual and company performance.

Benefits

• Competitive Medical, Dental, Vision, and Disability & Life insurance benefits. Low (free basic) employee Medical costs for employee-only coverage.
• Generous Paid Time off. All new hires start with 15 days of vacation, 4 personal days, 10 sick days, and 11 paid holidays. Plus your birthday off after 1 year of service! Additional vacation accrued with tenure.
• For onsite team members, onsite housing discount at Greystar-managed communities are available subject to discount and unit availability.
• 6-Week Paid Sabbatical after 10 years of service (and every 5 years thereafter).
• 401(k) with Company Match up to 6% of pay after 6 months of service.
• Paid Parental Leave and lifetime Fertility Benefit reimbursement up to $10,000 (includes adoption or surrogacy).
• Employee Assistance Program.
• Critical Illness, Accident, Hospital Indemnity, Pet Insurance and Legal Plans.
• Charitable giving program and benefits.