Fractional Controller

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

• Healthcare services or health technology experience, including work under HIPAA, is a big plus

•

What You’ll Bring to the Table

• Technical Accountant: You know GAAP deeply and can write a position that holds up to an auditor’s review.

• Independent Reviewer: You tell leadership when the numbers are right, and you say so plainly when they are not.

• Steady Hand: You apply the same policy period after period and document the reason for any change.

• Operator: You direct an outside team with clear standards, deadlines, and review.

• Business Partner: You understand that cost classification shapes how the company is managed, and you explain accounting choices in plain language.

• Systems Thinker: You build processes and documentation that hold up as the company grows.

•

What Success Looks Like Within the first 90 days, we expect you to have:

• Assessed our existing accounting practices and established a prioritized plan for bringing them to the next level.

• Established a consistent monthly close and review process with our outsourced accounting partner, including defined deadlines, responsibilities, and sign-off procedures.

• Documented our key accounting policies and identified any areas requiring additional technical analysis or adjustments.

• Established a defensible cost allocation methodology that supports customer-level gross margin reporting.

• Evaluated our existing accounting systems, identified scalability limitations, and recommended improvements to our financial reporting infrastructure.

• Ongoing success means accurate and timely financial reporting, well-documented accounting decisions, reliable unit economics, and an accounting function that can scale.

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