Tooling Program Manager

Clipboard
US
RemoteCareer-pivot friendly

Who this role is best for

Aimed at mid-level technical operations professionals who excel in systems thinking and cross-functional collaboration in a remote US setting.

Best fit for

  • Systems thinkers who translate operational chaos into scalable automation solutions.
    — “Translate ambiguous operational problems into scalable, systems-level solutions
  • Delivery-focused ICs comfortable owning roadmap decisions without managerial oversight.
    — “Define and own the quarterly roadmap for AI and automation tooling
  • Cross-functional navigators who resolve team friction through direct communication.
    — “Navigate cross-functional dynamics across Ops, Engineering, and Product

Things to consider

  • People management expectations begin within 6-12 months of hiring.
    — “This role offers a path toward people management within 6–12 months
  • Case study and multiple leadership interviews required in hiring process.
    — “Case Study 3. Case Interview with one of our team members

How to stand out

  • Quantify efficiency gains from past tooling projects in your resume.
    — “anchored to clear efficiency outcomes
  • Prepare examples of resolving cross-functional conflicts without escalation.
    — “resolve cross-functional challenges without unnecessary escalation
  • Demonstrate mentorship experience to signal leadership readiness.
    — “You’ve mentored or supported others
Pace · Fast PacedCollaboration · HighAutonomy · MediumDecision Impact · TeamLevel · Senior

Derived from job-description analysis by Serendipath's career intelligence engine.

What success looks like

  • define and own the quarterly roadmap
  • drive end-to-end delivery
  • navigate cross-functional dynamics
Typical background
program managementoperationsengineering

Skills & requirements

Required

Program ManagementCross-functional CollaborationTechnical Portfolio ThinkingExecution Discipline

Preferred

Ai-driven AutomationOperations Experience

Stack & domain

AIAutomationProgram ManagementLeadershipCommunicationHealthcareStaffing

About the role

Original posting from Clipboard via Ashby

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 https://www.ycombinator.com/topcompanies/ 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.

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.

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 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

HIRING PROCESS

  • 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 https://forms.gle/SyGaxHFbon7Hg9fW6.

Source: Clipboard careers (Ashby)

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