AI Strategy Director

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

Benefits offered by this job

Health, dental, and vision insurance

Competitive 401(k) matching

Paid Time Off

Autonomy and high-visibility role

Job summary

Accommodations Plus International (API) in Melville, NY seeks an AI Strategy Director to own the AI Enablement program—cadence, experimentation discipline, adoption metrics, and vendor management—driving measurable productivity.

This remote role partners with the CSO and EVP of Strategy & Innovation to align and execute strategic initiatives, including corporate development, AI rollout, and ROI optimization across the organization.

Qualifications

• Must have working fluency with Claude and enterprise AI tooling.
• 2–5 years of experience in program management or strategy roles.
• Ability to produce CEO- and board-quality artifacts.
• Comfort operating in ambiguity within a fast-moving team.

Responsibilities

• Lead AI experiments portfolio from intake to production.
• Manage AI pilots end-to-end with vendor coordination.
• Drive organization-wide adoption of Claude Enterprise and Copilot.
• Co-lead AI sandbox management with Engineering.
• Identify high-value AI use cases and improve ROI.
• Support strategy execution and inorganic growth activities.
• Prepare board and investor materials.

Skills

Claude proficiency

Experiment design

Program management

Strategic planning

Cross-functional collaboration

Education

Bachelor's degree in CS/Engineering/Quantitative field

Tools

Claude Enterprise

Microsoft Copilot

Job description

Accommodations Plus International (API) is a technology and services company focused on driving innovation across the travel and transportation industry. We partner with organizations in the airline, cruise, and rail sectors to deliver solutions that improve layover operations, enhance customer experience, and support long-term growth.

Our mission is to make layovers simpler and more efficient for crew members—and we bring that to life through deep industry expertise and a practical, results-driven approach.

Today, API’s platform powers over 18 million crew room nights each year for 100+ airlines and travel operators worldwide. Our Global Reach ensures that airline crews are rested, transported, and connected so global aviation runs on time.

At API, we’re building a culture rooted in succeeding and thriving together. It’s a place where people are encouraged to take ownership, develop their skills, and contribute to work that matters.

If you’re looking to grow your career in a company that values steady progress, real impact, and long-term development, we’d like to meet you!

Position Overview:

The AI Strategy Director 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.

What You’ll Do
Essential Functions: Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
Key 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 utilization from license to behavior. Produce the monthly AI scorecard: experiments launched, seats utilized, automation rates, FTE‑equivalent savings, and experiments graduated.
• Sandbox operations — Co‑lead AI sandbox management with Engineering. Manage onboarding from initial cohort through expansion, including use‑case intake, prioritization, and graduation criteria.
• Internal AI optimization — 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.
• 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 organization. Support corporate development and inorganic growth activities, board and investor materials, VCP reporting, and ad hoc strategic projects on the CSO’s agenda.

What You’ll Bring
Minimum Qualifications

• 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.

Preferred Qualifications

• 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.

Education
Bachelor’s degree required. Technical or quantitative field (computer science, engineering, economics, mathematics, data science) preferred. Advanced degree welcome but not required.

Position Type and Expected Hours of Work
Full time, Monday through Friday, normal core business hours and as needed on nights and weekends unless otherwise specified.

Supervisory Responsibility
Individual contributor role. No direct reports at hire. May supervise contractors, vendors, or interns supporting AI Enablement initiatives.

Travel Requirements
Occasional travel to API headquarters in Melville, NY and to vendor or partner sites, estimated at less than 10% of working time.

What’s In it for You

• Health, dental, and vision insurance
• Competitive 401(k) matching
• Paid Time Off
• AI mastery and hands‑on building with frontier AI tools
• AI Enablement skillset and experience across an enterprise rollout
• Program management experience on a high‑visibility, board‑tracked initiative
• High‑growth company environment backed by private equity
• High autonomy and entrepreneurial role with direct CSO and EVP engagement

Compensation
Compensation is determined based on several factors, including the candidate’s experience, qualifications, skill set, and location, as well as internal equity and external market benchmarks.
The good faith annual salary range for this position is $130,000 to $175,000, plus a discretionary 10% bonus.

Other Duties

Duties, responsibilities and activities may change at any time according to business needs.

The performance of additional responsibilities if you are designated as a Data Protection Champion (DPC), Senior Information Risk Owner (SIRO) or Information Assurance Accounting Officer (IAAO).

This position operates in a professional office environment. This role routinely uses standard office equipment such as computers, phones, photocopiers, filing cabinets and fax machines.

Physical Demands

The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. While performing the duties of this job, the employee is regularly required to talk or hear. The employee frequently is required to stand, walk; use hands to finger, handle or feel; and reach with hands and arms.

AAP/EEO Statement

Accommodations Plus International is an Equal Opportunity Employer that does not discriminate on the basis of actual or perceived race, creed, color, religion, alienage or national origin, ancestry, citizenship status, age, disability or handicap, sex, marital status, veteran status, sexual orientation, genetic information, arrest record, or any other characteristic protected by applicable federal, state or local laws. Our management team is dedicated to this policy with respect to recruitment, hiring, placement, promotion, transfer, training, compensation, benefits, employee activities and general treatment during employment.