AI Strategy & Enablement Director

Accommodations Plus International; Melville (NY); On-site; USD 130,000 - 175,000; Full time

Benefits offered by this job

Health, dental, and vision insurance

Competitive 401(k) matching

Paid Time Off

AI mastery and hands-on building with‑

Frontier AI tools access

Job summary

Accommodations Plus International is seeking an AI Strategy Analyst to own the operational backbone of the AI Enablement program, driving cross-functional cadence, experimentation discipline, adoption measurement, and vendor management. The role sits in the Strategy function and includes corporate development and inorganic growth activities, with remote work flexibility.

Ideal candidates bring 2–5 years in programme management or strategy roles, fluency with Claude and Copilot, and strong

Qualifications

• Must be fluent with Claude and other enterprise AI tooling.
• 2–5 years of professional experience in programme management, strategy operations, consulting, PE, or transformation roles.
• Strong written communication; ability to produce CEO- and board-quality artefacts.
• Comfort operating in ambiguity within a small, fast-moving team.

Responsibilities

• Experimentation portfolio — Run intake, hypothesis design, metric definition, and outcome documentation for AI experiments across Engineering, Client Delivery, and Corporate functions. Drive go/no-go reviews and graduation-to-production decisions.
• Pilot management — Run end-to-end management of AI pilots across the portfolio. Own validation evidence, vendor coordination, integration readiness, and graduation decisions.
• Adoption and management — Partner to drive org-wide training, communications, and enablement for Claude Enterprise and Microsoft Copilot. Move seat utilisation from license to behaviour. Produce the monthly AI scorecard: experiments launched, seats utilised, automation rates, FTE-eq savings, and experiments graduated.
• Sandbox operations — Co-lead AI sandbox management with Engineering. Manage onboarding from initial cohort through expansion, including use-case intake, prioritisation, and graduation criteria.
• Internal AI optimisation — Work with IT and internal stakeholders to manage, analyse, and optimise internal utilisation of AI across the organisation — identifying gaps, surfacing high-value use cases, and improving return on AI spend.
• Vendor and budget management — Own day-to-day relationship management for AI tooling vendors and the sandbox platform. Track spend against the approved Opex plan and flag variances.
• Strategy execution — Drive alignment and execution on strategic initiatives across the organisation. Support corporate development and inorganic growth activities, board and investor materials, VCP reporting, and ad-hoc strategic projects on the CSO’s agenda.

Skills

Claude Enterprise fluency

Microsoft Copilot

Cross-functional project mgmt

Executive communication

Education

Bachelor’s degree

Tools

Claude Enterprise

Microsoft Copilot

Job description

Accommodations Plus International is seeking an AI Strategy Analyst to own the operational backbone of the AI Enablement program, driving cross-functional cadence, experimentation discipline, adoption measurement, and vendor management. The role sits in the Strategy function and includes corporate development and inorganic growth activities, with remote work flexibility.

Ideal candidates bring 2–5 years in programme management or strategy roles, fluency with Claude and Copilot, and strong