Tooling Program Manager (AI)

TL;DR

Tooling Program Manager (AI/Automation): Owning and scaling internal automation and AI tooling portfolios to improve agent efficiency with an accent on roadmap definition and systems-level solutions. Focus on driving end-to-end delivery of complex initiatives and bridging the gap between Operations, Engineering, and Product.

Location: Remote (United States)

Salary: $120k – $140k

Company

An app-based marketplace connecting healthcare professionals with workplaces to provide essential care across the U.S.

What you will do

• Define and own the quarterly roadmap for AI and automation tooling, anchored to efficiency outcomes.
• Translate ambiguous operational problems into scalable, systems-level solutions.
• Drive end-to-end delivery across discovery, scoping, build, and launch for multiple concurrent initiatives.
• Navigate cross-functional dynamics across Ops, Engineering, and Product to resolve friction.
• Set a high execution bar by identifying issues early and driving continuous improvement.

Requirements

• Must be based in the United States.
• 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.
• Ability to design systems-level solutions from first principles, considering workflows and dependencies.

Culture & Benefits

• Remote-first work environment in a profitable Y-Combinator company.
• Clear path toward people management within 6–12 months based on performance.
• Mission-driven culture focused on uplifting communities and providing financial stability.
• High-performance environment emphasizing delivery velocity and end-to-end ownership.

Hiring process

• Initial application and Case Study.
• Case Interview and technical interviews with the Head of Core Services and Head of Operations.
• Final Culture Interview with an Executive Leader.