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HEAD OF AI & ENABLEMENT

Vice President Level | Remote with Travel

THE COMPANY

A PE-backed, high-growth hospitality and property management platform operating 50+ brands across the US. The business has been under private equity ownership for approximately 10 years and is entering an aggressive growth phase — expected to double in size within 18 months through both organic growth and M&A. The company operates with a distributed, brand-level model across multiple US locations. Headcount in IT is approximately 10, with offshore resources and a dedicated data warehouse team already in place. The CEO reports directly to a PE sponsor with high expectations for technology-driven value creation.

THE OPPORTUNITY

This is a newly created, greenfield role — the first of its kind at this company. The data infrastructure is further along than most organizations of this size: a modern data stack is in place with Snowflake, dbt, and live dashboards across Operations, Finance, and Business Development. What's missing is the person who bridges that foundation and the 50+ brands that need to use it. That's this role.

The company is a heavy Claude user. They use a significant amount of off-the-shelf SaaS, are actively involved in M&A integration, and have begun building internal data and AI tools — but there's no dedicated owner for AI enablement, reusable prompt libraries, capability gap identification, or field-level technology adoption. That gap is this job.

The Head of AI & Enablement will own the full AI lifecycle — strategy, tool evaluation, pilots, rollout, and measurement — across the entire brand portfolio. In year one, the priority is getting into the field, earning trust with brand operators, and shipping two or three visible pilots before scaling through a team. This is a player-coach position built for someone who ships things.

WHAT MAKES THIS ROLE DIFFERENT

•    You will build the function from day one — no inherited process, no existing playbook to maintain.

•    The company values local solutions for local markets. Adoption is earned, not mandated.

•    The CEO (Jacob) is actively engaged in technology strategy — this role has direct visibility at the top.

•    The company is doubling in size in 18 months. Every acquisition adds brands and scope to this role.

•    The organization is not top-down. The person who succeeds here leads by demonstrating value, not by org chart authority.

WHAT YOU'LL DO

•    Own the company-wide AI enablement strategy: from identifying opportunities at the brand level to deploying tools, measuring adoption, and iterating.

•    Spend significant time in the field with brand operators — ask what they need, listen before you build, and translate real pain points into usable tools.

•    Build and maintain the AI governance framework: acceptable-use policy, architecture standards, and guardrails that make AI adoption easier, not harder.

•    Develop reusable prompt libraries and playbooks that Regional Technology Partners can deploy consistently across brands.

•    Evaluate SaaS and AI vendors — run proofs of concept, make build-vs-buy calls, and avoid tool sprawl.

•    Identify capability gaps: where AI could work but isn't, and where current tools are underutilized.

•    Support internal data tool development and help employees find and use information more effectively.

•    Deliver quarterly visibility into AI adoption, ROI, and roadmap progress to senior leadership.

•    Hire, develop, and lead 3 Regional Technology Partners and 1 AI/Automation Engineer as the team is built out.

•    Partner closely with the Data Platform Team, IT, Finance, and Operations to align AI priorities with business outcomes.

WHAT WE'RE LOOKING FOR

Profile, not pedigree. This role could be filled by a smaller-company CTO, a consultant who actually knows how to build their own mandate, a heads-down AI practitioner who's ready to lead, or someone who's been a CIO at a business-forward company and wants to get their hands back in the work. What matters is the combination of traits below.

You are a change agent.

You shift how people work through demonstrated value, not mandate. Change feels like the obvious next step when you're involved, not something imposed. You know how to manage resistance and build momentum across a distributed, skeptical audience.

You are a Claude power user.

You have hands-on depth with LLM-based tools — Anthropic Claude specifically. You can speak to what you've built, how you've deployed it, and what you've learned. You understand agentic workflows, multi-agent systems, and where AI creates real business leverage vs. noise.

You roll up your sleeves.

You personally ship things before you scale through a team. You are visible in the field, credible with operators, and comfortable doing the work yourself when the situation calls for it.

You are technically curious, not technically narrow.

You don't need deep Snowflake expertise — but you need to be fluent enough across modern data stacks, workflow automation tools (N8N, Zapier, Make), and app/dev environments to make smart decisions and earn respect from engineers.

You ask uncomfortable questions.

You push back on low-ambition thinking. You challenge convention constructively, without losing the room. You don't hide behind the CIO — you advocate directly for what you believe.

You've grown and scaled things.

You've built teams, built playbooks, and expanded your footprint inside an organization. You understand what it takes to go from greenfield to operational, and you've done it.

SPECIFIC EXPERIENCE

•    7+ years in technology leadership, with at least 3 in AI, product, or digital transformation.

•    Proven track record delivering AI or automation projects end-to-end — not just advising on them.

•    Hands-on experience with LLM-based tools (Claude, OpenAI), workflow automation, and modern data stacks.

•    Experience designing and deploying multi-agent AI systems — orchestrating agents, HITL checkpoints, drift monitoring, and incident runbooks.

•    Experience building AI governance frameworks: acceptable-use policy, architecture standards, end-user guardrails.

•    Experience managing technical teams and translating between field operations and engineering.

•    Application or dev background — someone who's worked around systems and understands how software gets built.

•    Experience in distributed, multi-brand, or multi-location businesses preferred.

•    Commercial instinct — you tie AI investment to EBITDA, unit economics, guest satisfaction, or owner retention, not just tech metrics.

HOW YOU'LL BE MEASURED — YEAR ONE

•    AI tool adoption across the brand portfolio.

•    Time-to-value: from pilot idea to measurable business impact.

•    Contribution to the company's five value drivers: M&A integration, organic growth, margin expansion, TRevPAR, and owner retention.

•    Team build-out: hiring and ramping the Regional Technology Partner team.

•    Governance foundation in place: acceptable-use policy, reusable prompt libraries, and architecture standards published and in use.

STRUCTURE

•    Remote-friendly; meaningful travel to brand locations and offices required

Reports to the Chief Information Officer