Tooling Program Manager at Clipboard

WHY CLIPBOARD EXISTS: We exist to lift as many people up the socioeconomic ladder as possible. We dramatically improve lives by letting professionals turn extra time and ambition into career growth and financial opportunity. We achieve this with our app-based marketplace that connects workplaces and professionals, allowing professionals to book on-demand shifts and workplaces to access on-demand talent. ABOUT CLIPBOARD: Clipboard is a fast-growing Series C marketplace. We are a leader in our Long Term Care vertical and are expanding into several others (Dental, Home Health, etc.), as well as building out a full-time product. We are a YC Top Company [Upgrade to PRO to see link] with a global, remote team of 1,000+ people. We have been profitable since 2022, and fill millions of shifts annually at partner workplaces across the U.S., where tens of thousands of professionals work with us every year. We are looking for your help to keep growing so we can serve more professionals and workplaces. To learn more about us, take a look at our website here [Upgrade to PRO to see link] ABOUT THE ROLE The Technical Operations team is hiring a 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. You’ll grow into a people management role within 6–12 months by building strong delivery velocity, owning the roadmap end-to-end, and demonstrating the ability to develop and hold junior team members accountable. WHAT YOU’LL DO - 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 WHAT WE'RE LOOKING FOR - Technical Portfolio Thinking - You break down complex business problems and design systems-level solutions from first principles. You think in workflows, dependencies, and tradeoffs not just features. - 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. NICE TO HAVE - 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 Quick Note on Scammers: Clipboard would never ask you for money or your bank details to participate in our hiring process. Report any scammers impersonating the Clipboard hiring team members here [Upgrade to PRO to see link]