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
As we scale across new clients and specialties, we're investing in the operational infrastructure, systems, tooling, reporting, and analysis that lets our teams move faster and make better decisions.
This is a high-leverage, early-career role for someone hungry to learn how a healthcare AI company operates from the inside. You'll sit across Partner Operations, Implementations, and Commercial, working shoulder-to-shoulder with the teams doing the work, identifying where operational lift would unlock meaningful impact, and building the tooling and reporting to make it happen. Think of this as an internal automation and efficiency role: your job is to make our operators more effective, eliminate friction, and scale what works.
What You'll Do
Drive Internal Automation & Efficiency: Work directly with Partner Ops, Implementations, and Commercial to understand their workflows, surface opportunities to move faster, and deploy solutions yourself. Evaluate and implement agentic and AI tools that extend what our teams can do.
Build Reporting & Analytics Infrastructure: Own the throughput, productivity, and quality metrics that leadership and clients rely on. Deliver clean weekly roll-ups, run ad hoc analyses when something looks off, and proactively surface risks before they become escalations.
QA New Product Features: Test features as they ship, catch issues early, and close the feedback loop back to product and engineering.
Support Client Go-Lives: Help with capacity planning and operational readiness as new clients come online.
Institutionalize What Works: Capture SOPs and operational playbooks so what we learn in one corner of the business scales across the whole team.
What You'll Need
1 to 4 years of experience, ideally at a healthcare startup. Deep domain expertise isn't required, but familiarity with the pace and ambiguity of an early-stage healthcare company matters.
Fluent with agentic and AI tools (Claude, ChatGPT, Cursor, n8n, Zapier, or similar) and actively looking for ways to apply them
Strong data analysis skills and comfort pulling, cleaning, and analyzing data; SQL is a plus, not a requirement
Clear, direct written communication; you can turn messy operational reality into a crisp update
Experience working cross-functionally with operational and technical teams
What You'll Bring
A bias toward action: you'd rather get a rough version in front of the team Monday than a polished one in three weeks
Systems thinking: you see workflows as connected systems, not isolated tasks, and design accordingly
Hunger and ambition: you treat every gap you find as something you might own
Comfort with ambiguity and multiple concurrent workstreams
Nice to Have
Prior experience at a healthcare AI, care management, RCM, or provider operations company
Exposure to patient access, revenue cycle, or clinical operations workflows
Light technical skills (Python, scripting, API basics)
Benefits & Perks
Cutting-edge technology: Work directly with the latest advancements in AI and automation, tackling challenging problems that meaningfully impact healthcare.
Ownership & growth: You'll join Ascertain at a pivotal early stage, shaping our products, operations, and culture, with significant opportunities for career advancement.
Collaborative team: Join a talented, passionate, and supportive team with backgrounds from top tech companies and clinical institutions.
Flexible remote work: We support a flexible hybrid or remote working model, trusting you to manage your own schedule.
Competitive compensation: Competitive salary, meaningful equity, comprehensive health insurance, and more.
Why Ascertain? Make a real difference: Your work will directly impact healthcare organizations and improve patient care. Join Ascertain in transforming healthcare with AI!
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