Founding Product Manager

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.

The Role

We’re looking for a customer-obsessed and technical leader to own and scale our provider, payer, and vendor integrations at Ascertain. You’ll work at the intersection of complex healthcare workflows and AI automation, while enabling rapid customer delivery. As one of the first product managers, you’ll also help establish best product practices across the organization and play a key role in growing the product org..This is a highly customer-embedded role: you’ll shadow customers, define automation requirements, and ensure engineering builds solutions that deliver measurable ROI.

Reporting Structure:Reports to Chief Product Officer, works closely with Commercial and Customer Success teams.

What You’ll Do

• Develop and execute on Ascertain’s strategy for AI-driven and AI-managed integrations

• Perform up-front discovery through workflow shadowing, research, and competitive analysis and present findings to the team with conviction and rigor

• Prioritize the integrations with partners and vendors which will drive the most leverage for our team as we scale and expand into new use cases

• Partner with Customer Success to define acceptance criteria, testing protocols, and ensure high-quality delivery

• Track usage, performance metrics, and customer feedback, to continuously improve the quality of our product

What You’ll Need

• 4+ years of product management experience in B2B SaaS (previous product-focused engineering experience qualifies)

• Direct experience building customer-informed products (including workflow shadowing)

• Strong background in technical products with API and integration requirements (comfortable w/ curl, postman, etc.)

• Ability to translate complex processes into structured product specifications

• Experience working cross-functionally with engineering and go-to-market teams

What Will Help You Thrive

• Startup experience (Series A–B) in high-growth environments

• Previous experience as an engineer

• Comfort operating in ambiguity with a bias toward action

• Strong executive communication and systems thinking

• Familiarity with healthcare integrations (HL7, FHIR, EDI) and compliance (HIPAA, SOC 2)

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