Founding Product Manager, Healthcare AI Automation

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 need a Product Manager who thrives in the intersection of complex healthcare workflows, AI automation, and rapid customer delivery. You’ll own customer implementations, have opportunities to attain expansion revenue, and become critical as we scale. 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

• Shadow customer operations to identify automation opportunities and translate complex healthcare workflows into clear product requirements and future-state designs
• Prioritize features across specialties while driving EHR integrations (Epic, Athena, NextGen), payer portals, and API strategy
• Partner with Customer Success to enable implementations, define acceptance criteria and testing protocols, and ensure high-quality delivery
• Track adoption, customer feedback, and implementation metrics to continuously improve performance
• Use data to inform roadmap decisions, drive expansion revenue, and present product strategy to executive leadership and external stakeholders

What You’ll Need

• 4+ years of product management experience in B2B SaaS
• Direct experience building customer-informed products (including workflow shadowing)
• Strong background in technical products with API and integration requirements
• 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
• Implementation experience deploying software at customer sites
• 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! Compensation Range: $120K - $150K