AI Tooling Program Manager

About Clipboard

Our mission is to uplift as many communities as possible. We do this through our app-based marketplace that connects healthcare professionals with the workplaces that need amazing workers. This enables hundreds of thousands of people to achieve financial stability for themselves and their families while providing essential care to millions of people across the U.S.

Founded in 2016, we are a remote-first team of over 1,000 people building a top Y-Combinator company and have been profitable since 2022. We’re the leader in Long-Term Care staffing and are rapidly expanding into Home Health, Hospitals, and more, meaning we have more work to do than people to do it, and are growing our team to support millions more people and their communities.

Our team is hiring an AI Tooling Program Manager to own and scale our internal automation and AI tooling portfolio. This is a senior individual contributor role with program-level ownership; you'll define the roadmap, drive delivery across multiple concurrent initiatives, and partner directly with Operations leadership to hit agent efficiency targets.
This is not a traditional program manager role. Success comes from breaking down ambiguous operational problems, identifying root causes, making high-quality decisions with imperfect information, and delivering measurable business outcomes.

This role offers a path toward people management within 6–12 months, based on performance. Progression along this path will be driven by demonstrating strong delivery velocity, taking end-to-end ownership of the roadmap, and showing the ability to develop and hold junior team members accountable.

• Define and own the quarterly roadmap for AI and automation tooling, anchored to clear efficiency outcomes.

• Translate ambiguous operational problems into scalable, systems-level solutions

• Drive end-to-end delivery across discovery, scoping, build, and launch keeping multiple complex initiatives on track

• Set and uphold a high execution bar by diving into the details, identifying issues early, and driving continuous improvement

• Navigate cross-functional dynamics across Ops, Engineering, and Product, proactively identifying friction and resolving it directly

• Technical Portfolio Thinking - You break down complex business problems and design systems-level solutions from first principles. You think in workflows, dependencies, and tradeoffs, and you can translate the thinking into clear requirements engineering can build against.

• Product Management - You define requirements, prioritise a roadmap against constraints, and ship with engineering.

• Execution Discipline - You have a clear model for excellent project execution from discovery through delivery. You know when to stay high-level and when to go deep, and you catch issues before they become blockers.

• Stakeholder Influence - You communicate directly and effectively across functions. You identify misalignment early and resolve cross-functional challenges without unnecessary escalation.

• Leadership Trajectory - You’re motivated to grow into a people management role. You’ve mentored or supported others and care about raising the bar for the team, not just delivering your own work.

• Experience building or scaling internal tooling in high-growth environments

• Familiarity with AI-driven automation and its practical application to operational workflows

• Background in Ops, Support, or CX, with a deep understanding of user needs and pain points