Fractional Controller

Ascertain

1d•$8,000 - $11,000•Hybrid

About The Position

Ascertain is building AI agents to automate administrative work for care teams, serving major health systems and large specialty groups. The company is backed by Northwell Health and Deerfield Management and aims to restore time, trust, and focus to healthcare workers. The Fractional Controller owns the integrity of Ascertain’s financial reporting and the accounting judgments behind it. The role works directly with the Director of Operations & Finance and directs an outsourced accounting partner. The partner handles transaction processing and the monthly close; the Controller establishes accounting policy, reviews and signs off on the close, and ensures financial statements can withstand scrutiny from auditors, investors, and partners. The Controller also owns cost data supporting unit economics for the company’s software and services revenue. This contract engagement is about two days per week, including one day on site at the Durham office, with an option to increase the commitment as the company grows.

Requirements

Active CPA license.
At least 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.

Nice To Haves

Healthcare services or health technology experience, including work under HIPAA.

Responsibilities

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.
Oversee the monthly close performed by the outsourced accounting partner; review and approve reconciliations, journal entries, revenue schedules, and financial statements against the close calendar.
Provide technical accounting leadership to the outsourced accounting partner, set review standards, resolve accounting issues, and ensure accountability for agreed deliverables.
Develop and maintain a defensible methodology for allocating labor, infrastructure, and other delivery costs.
Produce monthly gross margin analysis by customer and revenue stream, reconciled to the general ledger.
Establish and maintain accounting documentation, reconciliations, supporting schedules, and internal controls for audit readiness.
Coordinate with external auditors and tax advisors on accounting matters, financial reporting, and compliance requirements.
Assess accounting systems and processes, identify improvement opportunities, 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.