---
title: 'Fractional Controller at Ascertain'
canonical: 'https://feeny.ai/job/fractional-controller-ascertain-remote-mtx4v9jrf0kj'
type: 'job'
last_seen: '2026-11-07'
---

# Fractional Controller at Ascertain

- **Company:** Ascertain
- **Location:** Remote
- **Employment:** contract
- **Work type:** remote
- **Posted:** 2026-11-06
- **Last confirmed live:** 2026-11-07
- **Apply:** https://jobs.ashbyhq.com/ascertain/18fa4c8e-8f38-4bb8-addd-8c8fca3b844a

## Job description

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!

## About Ascertain

## Company Overview
- **One-liner**: Ascertain provides an agentic AI platform that automates healthcare administrative workflows—prior authorizations, referrals, eligibility checks, care coordination, and claims management—across health systems, providers, and payers.
- **Entity Type**: Private (startup); raised $17.4M total (Seed + Series A)
- **Headquarters**: New York, New York, United States
- **Founded**: 2022
- **Founders**: Founded by a team of healthcare operators and technologists, including CEO Mark Michalski, MD (former healthcare executive) and CPO Eli Bernstein (others from Northwell Health and Aegis Ventures) [ascertain.com](https://www.ascertain.com/company) [linkedin.com](https://www.linkedin.com/company/ascertain-ai)

## Core Business
- **Primary industry**: Healthcare IT / AI-powered healthcare operations automation
- **Target customers**: B2B – health systems, specialty practices, management service organizations (MSOs), and health plans
- **Mission**: “To fundamentally transform medicine and create a more equitable healthcare future by addressing operational inefficiencies at scale” [linkedin.com](https://www.linkedin.com/company/ascertain-ai)

## Products & Services
Ascertain’s platform is a unified AI agent system that automates end-to-end care management and revenue cycle workflows. Key modules include:
- **Prior Authorization Automation**: Submits, reviews, and follows up on prior authorizations, reducing workload by up to 95% in pilot studies.
- **Referral Management**: Ingests unstructured data and automates referral processing.
- **Eligibility Verification**: Real-time checks integrated into existing workflows.
- **Care Coordination**: Automates discharge planning, care gap identification, and case management.
- **Claims Management**: Streamlines claims submission, denials, and appeals with built-in auditability.
- **Utilization Management**: Automates reviews and compliance checks.
- **Human-in-the-Loop**: Every process embeds human review for transparency and control [ascertain.com](https://www.ascertain.com/)

## Market Standing
- **Valuation / Market Cap**: Not disclosed
- **Key Metric (Total Funding)**: $17.4M (Seed $7.4M in March 2024, Series A $10M in May 2025)
- **Notable Investors / Partners**: Deerfield Management (Series A lead), Northwell Health (strategic partner and investor), Aegis Ventures (co-founder/sponsor) [linkedin.com](https://www.linkedin.com/company/ascertain-ai) [ascertain.com](https://www.ascertain.com/company)
- **Growth Signals**:
  - Headcount: 31 employees (93.1% YoY growth) [linkedin.com](https://www.linkedin.com/company/ascertain-ai)
  - Pilot with Northwell Health: reduced user clicks by 80% and authorization submission time by 67% [ascertain.com](https://www.ascertain.com/)
  - Partnership with The Oncology Institute (100+ oncology clinics) went live in 8 weeks [ascertain.com](https://www.ascertain.com/)
  - Partnership with Cardiovascular Associates of America (CVAUSA) [ascertain.com](https://www.ascertain.com/)
  - Claims ROI in under 90 days [ascertain.com](https://www.ascertain.com/)

## Competitive Advantages
- **Healthcare-native design**: Built by former healthcare operators who understand workflow complexity.
- **Agentic AI, not RPA**: Platform adapts to new rules in real time, ingests both structured and unstructured data, and operates with explainable, auditable guardrails.
- **Fast deployment**: Live in 8 weeks; ROI measurable in months.
- **Transparency & compliance**: Human-in-the-loop, built-in audit trails, and compliance-ready for healthcare regulations.
- **Strong partnerships**: Deep ties with Northwell Health (one of the largest health systems in the U.S.) provide real-world validation and data access [ascertain.com](https://www.ascertain.com/) [builtin.com](https://builtin.com/company/ascertain)

## Strategic Focus
- **Scale existing platform** across more health systems, specialty practices, and payers.
- **Expand automation** into denials management, population health, and care gap identification.
- **Deepen AI capabilities** while maintaining transparency and auditability.
- **Grow the team** (active hiring for product, engineering, and customer-facing roles) [linkedin.com](https://www.linkedin.com/company/ascertain-ai) [jobs.ashbyhq.com](https://jobs.ashbyhq.com/ascertain)

## Why Work Here
- **Mission-driven impact**: Work on reducing administrative burden that delays patient care; directly improve healthcare access and equity.
- **Culture**: “Clinicians, engineers, and business leaders” united by the belief that “less admin means better outcomes” [ascertain.com](https://www.ascertain.com/company)
- **Remote / Hybrid**: Some roles are remote (e.g., Brazil-based engineers), others are in-office or hybrid in New York. The company supports flexibility [builtin.com](https://builtin.com/company/ascertain) [linkedin.com](https://www.linkedin.com/company/ascertain-ai)
- **Engineering environment**: Apply cutting-edge AI (agents, LLMs, NLP) to real-world healthcare problems; work on a modern stack with fast iteration cycles.
- **Growth trajectory**: Rapidly growing startup (93% headcount growth YoY) with strong funding and strategic partnerships; opportunities for ownership and advancement.
- **Notable perks**: Not explicitly detailed, but typical for venture-backed AI startups (equity, competitive salary, mission-focused culture).

## Sources
1. [ascertain.com](https://www.ascertain.com/)
2. [ascertain.com/company](https://www.ascertain.com/company)
3. [ascertain.com/careers](https://www.ascertain.com/careers)
4. [linkedin.com/company/ascertain-ai](https://www.linkedin.com/company/ascertain-ai)
5. [builtin.com/company/ascertain](https://builtin.com/company/ascertain)

## Other roles at Ascertain

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- [Senior Full-Stack Engineer](https://feeny.ai/job/senior-full-stack-engineer-ascertain-remote-q1veaxn1v50f)
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