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

As Ascertain’s Fractional Controller, you will own the integrity of our financial reporting and the accounting judgments behind it. You will work directly with our Director of Operations & Finance and direct the work of our outsourced accounting partner.

This is not a bookkeeping role. Our accounting partner handles transaction processing and runs the monthly close. You will set accounting policy, review and sign off on the close, and make sure our financial statements hold up to scrutiny from auditors, investors, and partners.

You will also own the cost data behind our unit economics. We earn both software and services revenue from health systems and specialty groups. How we classify and allocate cost directly shapes how leadership manages the business.

This is a contract engagement of about two days per week, one of them on site in our Durham office. There is an option to increase the commitment as the company grows.

What You’ll Do

Accounting Policies & Technical Guidance: Establish and document GAAP-compliant accounting policies covering revenue recognition (ASC 606), cost of revenue, cost allocation, capitalized software, stock-based compensation, and accruals. Prepare technical accounting memos for material or complex accounting decisions.

Monthly Close & Financial Reporting: Oversee the monthly close process performed by our outsourced accounting partner. Review and approve reconciliations, journal entries, revenue schedules, and financial statements, ensuring accurate and timely reporting against an established close calendar.

Outsourced Accounting Oversight: Serve as the technical accounting lead for our outsourced accounting partner, providing guidance on complex transactions, establishing review standards, resolving accounting issues, and ensuring accountability for agreed deliverables.

Cost Accounting & Unit Economics: Develop and maintain a defensible methodology for allocating labor, infrastructure, and other delivery costs. Produce a monthly gross margin analysis by customer and revenue stream, reconciled to the general ledger, to support financial and operational decision-making.

Audit Readiness & Financial Controls: Establish and maintain the accounting documentation, reconciliations, supporting schedules, and internal controls necessary for audit readiness. Coordinate with external auditors and tax advisors on accounting matters, financial reporting, and compliance requirements.

Finance Systems & Scalability: Assess our existing accounting systems and processes, identify opportunities for improvement, and develop a roadmap for scalable financial infrastructure. Lead accounting requirements and implementation oversight for an ERP or other finance technology as business needs evolve.

What You’ll Need

Active CPA license

8+ years of accounting experience, beginning in public accounting

Controller or senior technical accounting experience at a venture-backed technology or healthcare company

Hands-on ASC 606 experience with contracts that include implementation fees, pilots, or usage-based pricing

Experience leading companies through financial statement audits and external financial reviews

Experience designing cost allocation and gross margin reporting for software or services businesses

Experience leading a finance systems or ERP implementation, such as NetSuite, Sage Intacct, or a comparable platform

Based in the Research Triangle area and able to work on site in Durham one day per week