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

You’ll be working on the Expand team, focusing on launching Ascertain into new product areas. You'll own which workflows we take on, in what order, and the product features required to deliver them. You'll spend real time inside doctor’s offices, watching people do this work manually and finding where it breaks, then turn what you learn into a product the next hundred customers can use.

Prior authorization is the workflow we understand best, so it's where you'll start and learn how our system behaves.

You'll report to the product lead for Expand. Day to day you'll work with engineers, a designer, and product ops, alongside the forward-deployed engineers and the implementations team who sit in front of customers.

What You'll Do

• Own a set of workflows end to end, including the outcome for the practice after launch

• Run discovery and shadowing sessions to understand our customers’ operations and then make the case for what's worth building

• Decide which parts of each build become product and which stay custom for one practice, with product engineering and the forward-deployed team

• Design for the capabilities of the future while considering where humans need to be involved today; delivering value for our partners while collecting data for future automation

• Write the acceptance criteria and own the rollout, including the parts that go wrong

Who you are

If you meet the required list, apply. The preferred qualifications are a bonus, not a requirement.

Required

• 4+ years in product management where you set the roadmap. At least 2 of those years working on software sold into a single industry (ex. healthcare, legal, logistics, construction or similar)

• You have replaced a manual process with software. You sat with the people doing the job by hand, worked out what the software should do instead, and shipped it

• Experience leveraging data and feedback to drive product improvements

• You deal with stakeholders gracefully i.e. you can pushback on a customer request in a way that builds trust rather than undercuts it.

• You can identify when a technical approach won’t meet customer needs and help identify alternatives

• Can draft clear briefs, specs, memos, etc. that remove the need for meetings

Preferred

• Prior authorization, revenue cycle or specialty healthcare experience

• Early-stage startup experience

• A design or engineering background

• You've shipped a product built on language models

What Will Help You Thrive

• Healthcare, revenue cycle, or prior authorization exposure

• Early-stage startup experience

• Prior design or engineering background

• Experience with AI or LLM products

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