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Manager, Financial and Operational Compliance

June 6, 2026

Who is Prescryptive?Prescryptive is the healthcare technology company enabling the direct access marketplace for prescription drugs. Our platform aligns incentives so affordability, choice, and patient access become the natural outcome of a functioning system. Learn more about us by following us on <a href="https://nam10.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.linkedin.com%2Fcompany%2Fprescryptive%2F&data=05%7C02%7CMegan.Keefe%40prescryptive.com%7Cd6da731f50c84205e7ac08de7e0109e9%7Cd100e6e9594f4c5fabbe0eaa95dd2870%7C0%7C0%7C639086740112041482%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=Kv%2ByVE6zfLdDHLywqN3RHJK182n%2FqNu0FOcEZppehf0%3D&reserved=0" target="_blank" rel="noopener noreferrer">LinkedIn</a> or visiting <a href="https://nam10.safelinks.protection.outlook.com/?url=https%3A%2F%2Fprescryptive.com%2F&data=05%7C02%7CMegan.Keefe%40prescryptive.com%7Cd6da731f50c84205e7ac08de7e0109e9%7Cd100e6e9594f4c5fabbe0eaa95dd2870%7C0%7C0%7C639086740112067281%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=2AB6Le2kpIusbPrIJFYeVw4SbjJ9jDX6utDxswHmWsY%3D&reserved=0" target="_blank" rel="noopener noreferrer">Prescryptive.com</a>.  About this roleWe’re hiring a hands-on compliance leader to advance the control environment for a scaling healthcare technology business. This role is designed for someone who has experience implementing and overseeing a cross functional compliance framework, including end-to-end process documentation, controls, testing, and remediation. Reporting to the CFO, this leader will partner across Finance, Operations, and other business functions. This is a high-impact individual contributor role at the outset, with the potential to grow into team leadership as the function matures.What you will doProgram Design & Implementation <ul><li>Design and implement financial compliance framework following COSO and AICPA best practices, customized for mid-market scale</li><li>Conduct comprehensive risk assessment across all financial processes</li><li>Collaborate with the business to document key financial processes and identify, and document, key financial controls including objectives, ownership, frequency, evidence, and linkage to risks</li><li>Develop Risk and Control Matrix (RACM) serving as central repository for compliance program</li><li>Create practical testing procedures, documentation, and monitoring dashboards</li><li>Establish deficiency management protocols including classification, escalation, remediation workflows, and tracking</li><li>Maintain engagement with control owners</li></ul>Testing & Monitoring <ul><li>Execute quarterly testing of key controls</li><li>Perform semi-annual/annual testing of other significant controls</li><li>Monitor automated controls and analyze performance trends to identify emerging risks</li><li>Validate remediation effectiveness through follow-up testing</li><li>Coordinate with external auditors to support their control reliance strategy</li></ul>Deficiency Management & Remediation <ul><li>Identify, document, and classify control deficiencies using severity criteria (control deficiency, significant deficiency, material weakness)</li><li>Lead root cause analysis and collaborate with process owners on remediation plans</li><li>Track deficiency status, escalate overdue items, and ensure timely closure</li></ul>Reporting & Communication <ul><li>Prepare monthly status updates to CFO and quarterly compliance reports to Executive Leadership</li><li>Prepare annual control environment assessment for CFO and Board of Directors</li><li>Serve as primary liaison with external auditors on internal control matters</li></ul>What you will bring (minimum requirements)Education & Certification:<ul><li>Bachelor's degree in Accounting, Finance, or related field required</li><li>CPA license preferred (or active CPA candidate)</li></ul>Experience:<ul><li>7+ years of experience in internal controls, internal audit, compliance, finance, accounting, or related discipline</li><li>Experience with risk-based control frameworks, ideally building or maturing a controls or compliance framework in a growing organization</li></ul>Technical Skills:<ul><li>Strong knowledge of internal controls over financial reporting, GAAP, and financial statement assertions</li><li>Proficiency with COSO framework and audit standards</li><li>Advanced Excel skills</li><li>Familiarity with IT general controls and application controls</li></ul>Leadership & Soft Skills:<ul><li>Self-starter with strong project management skills—ability to create structure from ambiguous mandates</li><li>Excellent communication skills—ability to explain complex controls to non-technical audiences and influence without authority</li><li>Collaborative relationship builder who gains buy-in from process owners</li><li>Detail-oriented with strong analytical skills and ability to identify patterns and root causes</li><li>Pragmatic problem-solver who balances best practices with mid-market realities</li><li>Adaptable, resilient, and comfortable with ambiguity in a growing company</li><li>Leadership potential with ability to mentor, delegate, and evolve to team management</li><li>High integrity and professional skepticism</li></ul>Ideally you will also have<ul><li>Public accounting experience</li><li>CPA license, CIA, or CISA certification</li><li>Experience with GRC platforms</li><li>Healthcare, pharmacy, or financial services industry experience</li></ul>What we have to offer<ul><li>The opportunity to grow alongside an early-stage company shaking up a big, old-fashioned industry</li><li>Flexible time off, including 12 paid holidays</li><li>401k match plus 100% employer paid medical, dental, and vision premiums</li><li>Company contribution to Health Savings Account</li><li>Stock options</li></ul>Prescryptive is committed to fair pay practices. The projected annual salary for this position is $135,000 to $180,000. When preparing an offer, we consider the candidates resume, experience, interview feedback, internal equity, and location.Prescryptive is an Equal Opportunity Employer. Prescryptive does not discriminate on the basis of race, religion, color, sex, gender identity, sexual orientation, age, non-disqualifying physical or mental disability, national origin, veteran status or any other basis covered by appropriate law. All employment is decided on the basis of qualifications, merit, and business need.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

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Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

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Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...