Remote AI Strategy & Enablement Lead

Accommodations Plus International; United States; Remote; USD 130,000 - 165,000; Full time

Benefits offered by this job

Health insurance

Competitive 401(k) matching

Paid Time Off

AI mastery and frontier tools

High autonomy

Job summary

Accommodations Plus International seeks an AI Strategy Analyst to own the AI Enablement program’s operational backbone, coordinating experiments, pilots, adoption, and vendor management. This remote role offers high autonomy with direct CSO and EVP engagement.

You will drive ROI through AI-enabled processes and monetize opportunities, while collaborating across engineering, delivery, and corporate functions in a fast-moving, PE-backed setup.

Qualifications

• Must have fluency with Claude and other enterprise AI tooling.
• 2–5 years in program management, strategy ops, consulting, private equity, or transformation.
• Strong written communication for CEO- and board-quality artifacts.
• Comfort operating in ambiguity within a small, fast-moving team.

Responsibilities

• Experimentation portfolio: design hypotheses, define metrics, document outcomes.
• Pilot management: end-to-end AI pilots, validate evidence, coordinate vendors.
• Adoption and management: drive org-wide training, communications, and enablement for Claude Enterprise and Copilot.
• Sandbox operations: co-lead AI sandbox management, onboarding and graduation criteria.
• Internal AI optimization: identify gaps, surface high-value use cases, improve ROI.
• Vendor and budget management: track spend vs approved Opex, flag variances.
• Strategy execution: support corporate development and board/investor materials.

Skills

Claude Enterprise

Microsoft Copilot

Experiment design

Cross-functional PM

CEO/board communication

Ambiguity tolerance

Education

Bachelor’s degree

Technical/quantitative field

Job description

Accommodations Plus International seeks an AI Strategy Analyst to own the AI Enablement program’s operational backbone, coordinating experiments, pilots, adoption, and vendor management. This remote role offers high autonomy with direct CSO and EVP engagement.

You will drive ROI through AI-enabled processes and monetize opportunities, while collaborating across engineering, delivery, and corporate functions in a fast-moving, PE-backed setup.