AI Strategy Director

Who We Are

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 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.

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 othe…