Director of Enterprise AI

Recognized as the No. 1 site trusted by real estate professionals, ® has been at the forefront of online real estate for over 25 years, connecting buyers, sellers, and renters with trusted insights and expert guidance to find their perfect home. Through its robust suite of tools, ® not only makes a significant impact on the real estate industry at large, but for consumers, navigating the biggest purchase they will make in their life, by providing a user experience that is easy to use, easy to understand, and most of all, easy to make decisions.

Join us on our mission to empower more people to find their way home by breaking barriers to entry, making the right connections, and building confidence through expert guidance.

We're looking for a Director of Enterprise AI to scale our enterprise AI acceleration program from a small founding team into a full delivery, platform, and enablement organization. You'll lead applied AI transformation across every major business function - serving 600+ engineers and 2,000+ employees at one of the largest real estate technology platforms in the U.S.

This isn't a greenfield experiment. The model is validated: production agentic workflows are delivering up to 80% effort reduction, a backlog of project submissions spans every business unit, and three AI Solutions Engineers are already shipping. The challenge is turning early traction into a repeatable, scalable engine that delivers on our executive mandate for transformational AI-driven outcomes.

• Build and lead the organization. Scale the team from ~4 to ~15–18 people across three functions: AI Solutions Engineering (domain-aligned delivery pods serving Revenue, Marketing, Consumer, Corporate, and executive leadership), AI Platform & Infrastructure (LLM gateway, orchestration, governance, developer AI tooling), and AI Enablement & Programs. Recruit, develop, and retain top talent in a fast-emerging discipline.
• Drive delivery at scale. Own the end-to-end lifecycle for AI projects - from workshop-driven intake through build, handoff, support, and post-deployment measurement. Manage a portfolio of concurrent agentic workflow builds across business domains with established sprint cadences, capacity planning, and a clear ownership model where requesting teams maintain production systems after handoff.
• Stand up the AI platform. Build the infrastructure layer that makes delivery scalable and governed: centralized LLM gateway and model routing, orchestration platform hardening, credential management and audit logging across dozens of cloud accounts, AI tool governance (acceptable use policy, default-block enforcement, shadow AI mitigation), and the technical roadmap for our internal AI developer tooling.
• Scale enablement and adoption. Grow the program that initiated our current backlog, operationalize an AI champions network across business units, expand AI training curricula beyond three foundational courses with 650+ completions, and own executive-facing reporting and communications including monthly tech reviews and steering committee updates.
• Partner across the business. Serve as the primary enterprise AI partner to leaders in Revenue, Marketing, Consumer, HR, Finance, Legal, and Corporate Communications. Collaborate with Platform Engineering, Operations, and Security on shared infrastructure and compliance. Manage strategic vendor relationships across LLM providers and AI SaaS platforms. Present validated ROI and strategy to C-suite leadership.
• Own the budget. Manage a multi-million-dollar annual AI tooling portfolio with growth projected as adoption scales. Build business cases grounded in pre/post-implementation measurement, drive cost optimization across consumption-based pricing models, and demonstrate ROI through hours saved, FTEs avoided, and cycle-time reduction.

You're a builder-operator who has scaled an internal AI, ML, or…