AI Strategy Director

Accommodations Plus International•Melville, NY

19h•$130,000 - $175,000•Remote

About The Position

The AI Strategy Analyst owns the operational backbone of API’s AI Enablement program — the cross-functional cadence, experimentation discipline, adoption measurement, and vendor management that turn AI investment into measurable productivity and operating leverage. The role also has responsibility within the Strategy function to drive alignment and execution on strategic initiatives across the organization, including corporate development and inorganic growth activities. This is a remote position. Success in this Role Milestone: drive Claude Enterprise adoption and rollout; own AI Sandbox rollout and cross-functional use-case identification and development, including both internal and external (customer-facing) applications. Long-term contributions: drive API toward an AI-native end-state through leadership, training, and execution. Mastery: Claude as a daily working tool; development of AI-enabled processes and outcomes across internal operations and customer-facing applications. Impact: drive quantifiable ROI through dollar savings, efficiency generation, and AI productization and monetization. Engagement: direct engagement with the CSO and EVP of Strategy & Innovation; broad engagement opportunity across the organization and with external parties including investors, vendors, partners, and acquisition targets.

Requirements

Must have working personal fluency with Claude (mandatory) and other enterprise AI tooling (Microsoft Copilot or equivalent)
Demonstrated ability to design and document hypothesis-driven experiments.
2–5 years of professional experience in program management, strategy operations, consulting, private equity, or transformation roles, with demonstrated experience running cross-functional projects to measurable outcomes.
Strong written communication; ability to produce CEO- and board-quality artifacts.
Comfort operating in ambiguity within a small, fast-moving team.

Nice To Haves

Technical background (educational or professional) — computer science, engineering, data, or comparable hands-on experience with software, automation, or AI systems.
Exposure to voice AI, document automation, or contact-center modernization.
Prior experience in a PE-portfolio company or other high-growth, lean environment.

Responsibilities

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.
Run end-to-end management of AI pilots across the portfolio.
Own validation evidence, vendor coordination, integration readiness, and graduation decisions.
Partner to drive org-wide training, communications, and enablement for Claude Enterprise and Microsoft Copilot.
Move seat utilization from license to behavior.
Produce the monthly AI scorecard: experiments launched, seats utilized, automation rates, FTE-equivalent savings, and experiments graduated.
Co-lead AI sandbox management with Engineering.
Manage onboarding from initial cohort through expansion, including use-case intake, prioritization, and graduation criteria.
Work with IT and internal stakeholders to manage, analyze, and optimize internal utilization of AI across the organization — identifying gaps, surfacing high-value use cases, and improving return on AI spend.
Own day-to-day relationship management for AI tooling vendors and the sandbox platform.
Track spend against the approved Opex plan and flag variances.
Drive alignment and execution on strategic initiatives across the organization.
Support corporate development and inorganic growth activities, board and investor materials, VCP reporting, and ad hoc strategic projects on the CSO’s agenda.