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.
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.
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.
What You’ll DoDefine 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 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.
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
Application
Case Study
Case Interview with one of our team members
Interview with our Head of Core Services
Interview with our Head of Operations
Final Culture Interview with one of our Executive Leaders
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.
Skills Required
- Experience with technical portfolio thinking and system-level solutions
- Proven execution discipline in project management from discovery to delivery
- Ability to communicate effectively across cross-functional teams
- Motivation to grow into a people management role
- Experience building or scaling internal tooling
- Familiarity with AI-driven automation
- Background in Operations or Customer Experience
Clipboard Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Clipboard and has not been reviewed or approved by Clipboard.
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Leave & Time Off Breadth — Corporate materials emphasize remote-first work with unlimited PTO, flexible hours, and family leave options. Feedback suggests time-off flexibility is a notable positive for corporate roles.
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Healthcare Strength — Corporate roles are advertised with medical, dental, and vision insurance. Benefits pages and company materials indicate multiple health-plan options for W‑2 staff.
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Strong & Reliable Incentives — Instant or same-day payouts after shifts are prominently marketed and often work smoothly, aiding cash flow. Higher-paying urgent or surge shifts and in-app rate negotiation can lift earnings in some markets.
Clipboard Insights
What We Do
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.
Why Work With Us
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 Offices, Schools, etc). We are a YC Top Company with a global, remote team of 700+ people. We have been profitable since 2022, and fill millions of shifts annually at partner workplaces across the US.
