Technical Recruiter

Meet Ascertain

Ascertain is building AI agents to automate the administrative work that burdens care teams. We are in major health systems and large specialty groups, saving hundreds of staff hours every week.

Our backers include Northwell Health, New York’s largest health system, and Deerfield Management, a leading healthcare investment firm.

Together, we’re on a mission to restore time, trust, and focus to the people who keep healthcare running. Our work is urgent — not because of startup timelines, but because our customers rely on us to drive financial resilience and operational clarity in a system under strain.

About the Role

We’re entering a phase where the quality and consistency of our hiring will materially shape the company’s trajectory. This role exists to build a disciplined, high-bar recruiting function that scales with us.

The Technical Recruiter will partner directly with leadership to define hiring standards, design structured evaluation processes, build proactive pipelines across technical and GTM roles, and strengthen decision-making quality across the organization.

You will be responsible for designing, operating, and continuously improving our hiring engine—partnering directly with leadership to attract and close exceptional talent.

What You’ll Need

• 3-5 years of full-cycle recruiting experience, including time in a high-growth or venture-backed environment.

• Demonstrated experience building or significantly improving recruiting systems—not just running searches within an established structure.

• A track record of hiring high-performing technical and GTM talent in competitive markets.
  Strong outbound sourcing ability, including experience mapping talent markets and engaging passive candidates.

• Experience partnering directly with senior leaders on headcount planning, role definition, and hiring decisions.

• Deep familiarity with structured interviewing and evidence-based evaluation methods.

• Comfort using hiring data to diagnose funnel breakdowns and improve quality or speed.

• High ownership and accountability—you take responsibility for outcomes, not just activity.

What You’ll Bring to the Table

• Has operated in high-growth environments and understands how quickly hiring quality drifts without clear standards.

• Brings structure instinctively — clarifies role scope before a search begins, defines what “strong” actually means, and builds interviews that measure real signal rather than gut feel.

• Is a strong sourcing operator who can map markets, engage passive candidates thoughtfully, and compete for talent that isn’t actively looking.

• Is comfortable hiring across both technical and GTM functions, recognizing that each requires different search strategies and evaluation approaches.

• Partners confidently with senior leaders and is willing to challenge vague requirements or inconsistent feedback to improve decision quality.

• Elevates hiring manager judgment through calibration, clarity, and accountability.

• Uses data fluently but pragmatically; treats funnel metrics as diagnostic tools and can quickly identify where quality or velocity is breaking down.

• Operates with true ownership—if hiring quality drops, a search stalls, or standards drift, they step in and reset the bar.

Why Ascertain? Make a real difference: Your work will directly impact healthcare organizations and improve patient care. Join Ascertain in transforming healthcare with AI!