Chief of Staff to the CTO - AI Strategy & Special Projects

Confirmed live in the last 24 hours

Playlist (Mindbody / ClassPass parent co)

United States

On-site

Posted April 10, 2026

Job Description

About the Company:

At Playlist, life's richest moments happen when people step away from screens to move, connect, explore, and play. We're building the definitive platform for intentional living, connecting people with inspiring experiences in fitness, wellness, and beyond. With popular brands like Mindbody and ClassPass, Playlist empowers businesses and individuals, making it effortless for aspirations to become actions. Join us in reshaping technology's role to foster meaningful, real-world connections.

The Role You'll Play

Reporting directly to the CTO, you’ll lead hands-on AI special projects across Playlist and our portfolio (including Mindbody and ClassPass). This role blends technical program leadership with a Chief of Staff-style operating cadence: you’ll bring clarity to ambiguous work, create momentum across teams, and translate AI capabilities into practical leverage for how we build, support, and scale our products.

This is not a purely strategic role. You’ll be expected to get hands-on with AI tools like Claude and Codex to prototype, test, and iterate on real workflows. We’re looking for someone who doesn’t just shape AI strategy, but actively builds, turning ideas into lightweight, impactful solutions that drive real outcomes.

You Will:

Prototype and iterate on AI workflows and lightweight solutions using tools like Claude or Codex, focusing on adoption and impact
Independently scope and execute on AI-driven projects, taking a hands-on role from initial idea through lightweight implementation and iteration, and stepping in to drive work forward
Turn AI strategy into a clear, executable program with scoped initiatives, owners, milestones, and measurable outcomes
Partner across the company to identify high-impact AI opportunities and move them from idea to delivery
Establish and run the operating rhythm for AI work, including OKR support, program updates, and stakeholder communications
Unblock progress by coordinating dependencies, clarifying tradeoffs, and keeping teams aligned on decisions
Support responsible AI delivery by aligning on pragmatic guardrails and risk considerations appropriate to each use case
Provide clear, decision-ready updates to the CTO and leadership partners on progress, outcomes, and next steps

You’ll thrive in this role with experience in: 

5+ years leading cross-functional technical programs, initiatives, or special AI projects with multiple stakeholders
Strong ability to turn ambiguity into structured plans and drive consistent follow-through

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