Fractional Chief AI Officer - AI Transformation, Engineering Leadership

About the role

This role acts as a Technical Sidecar to our CEO — partnering directly with him to lead AI transformation for non-tech, mid-market businesses and help them become AI-first organizations.

Responsibilities

• Arcitect AI Strategies: Build custom AI adoption frameworks that enhance human expertise and scale output for non-tech mid-market businesses.
• Drive Implementation: Partner with product and engineering teams to operationalize AI across targeting, content, and revenue analytics.
• Client-Facing Leadership: Sit in front of CEOs and leadership teams of traditional businesses and lead their AI transformation end to end.
• Manage AI Governance: Own the strategy for AI safety, culture, and ethical execution to ensure long-term investment stability.
• C-Suite Advisory: Act as a "Sidecar" to our CEO and to client leadership teams, translating technical breakthroughs into actionable business plays.
• Audit & Optimization: Conduct deep-dive assessments to identify productivity gains and eliminate operational redundancies.
• Internal AI Enablement: Help OST's own engineering team become AI-first — ensuring our internal capabilities evolve alongside the engagements we deliver.

Requirements

• AI Transformation & Implementation: Proven track record of leading AI strategy from discovery to deployment, with measurable business outcomes.
• 10+ years of Engineering Leadership: Extensive experience as a CTO, VP of Engineering, or Engineering Lead in digital product environments.
• Fractional Consulting Background: Currently operating in a fractional, interim, or advisory capacity with multiple successful engagements.
• Hands-On Technical Depth: Ability to personally audit code and architecture — not just direct others. Must be comfortable getting into the stack when needed.
• Digital Transformation Expertise: History of leading complex migrations from legacy or standard digital systems to AI-integrated workflows.
• Outcome-Oriented Mindset: Ability to demonstrate clear ROI — cost reductions, time savings, revenue impact, operational efficiency gains.

Nice to have

• AI Certification: Formal certification as a Chief AI Officer or equivalent AI Executive training.
• B2B Agency Experience: Experience working within or for digital product studios or B2B professional services firms.
• Cybersecurity/Governance Knowledge: Experience in information security governance, AI risk management, and bias controls.
• Modern AI Stack Familiarity: Hands-on experience with LangChain, LangGraph, RAG architectures, or agentic AI frameworks.
• Private Equity or M&A Exposure: Experience working with PE-backed companies or supporting technology due diligence processes.

Pay

Competitive Rate: Commensurate with experience. We are open to discussing structures that work for both sides.

Schedule

Fully Remote: US-based preferred. Open to discussing exceptions for exceptional profiles.

Benefits & Compensation

• Long-Term Engagement: Starting with a 6-month engagement with the intention of continuity based on pipeline.
• Talent Referral Program: Earn a bonus for referring top-tier talent to our network.

To Apply

Please Send Your Resume In English. Include The Following LinkedIn Profile URL (required).

Portfolio or case studies demonstrating AI transformation outcomes (optional but valued).

Relevant Certifications (e.g., CAIO, AWS, Azure).

Cover Letter: Tell us about a time you turned a manual business process into a measurable outcome through AI or technology.