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General Counsel (Fractional)

April 30, 2026

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About Us At Sleep Doctor, we’re helping millions get a full night's rest. As the most trusted name in sleep health, we make better sleep possible with proven support, clear answers, and hands-on care that fits real life. Across our brands—SleepDoctor.com, SleepFoundation.org, and SleepApnea.org—we combine clinical expertise with consumer-first experiences to help people understand their sleep, tackle real challenges, and wake up to healthier, more energized lives. If you’re passionate about making better sleep possible—and want to help reshape the future of sleep care—we’d love to meet you. <div class="ng-tns-c67971978-16"> <section id="processing-state-0" class="processing-state_container is-gpi-avatar ng-tns-c67971978-16 ng-trigger ng-trigger-processingStateShowHide ng-star-inserted is-done-processing"> <div id="processing-state-0-summary" class="processing-state_details is-gpi-avatar ng-trigger ng-trigger-menuExpansion ng-tns-c67971978-16 ng-star-inserted"> <ul class="is-gpi-avatar ng-tns-c67971978-16 ng-star-inserted"> <li class="ng-tns-c67971978-16 ng-star-inserted">~20-30 Hours/Week <div class="tool-summary ng-tns-c67971978-16"> <div class="tool-summary-message ng-tns-c67971978-16 gds-body-l ng-star-inserted"> </div> </div> </li> </ul> </div> </section> </div> <div class="response-content ng-tns-c4138151739-15"> <div class="container"> <div id="model-response-message-contentr_eb982b935268b0cd" class="markdown markdown-main-panel tutor-markdown-rendering enable-updated-hr-color"> About Us At Sleep Doctor, we're helping millions get a full night's rest. As the most trusted name in sleep health, we make better sleep possible with proven support, clear answers, and hands-on care that fits real life. Across our brands—SleepDoctor.com, SleepFoundation.org, and Sleep Apnea.org—we combine clinical expertise with consumer-first experiences to help people understand their sleep, tackle real challenges, and wake up to healthier, more energized lives. If you're passionate about making better sleep possible—and want to help reshape the future of sleep care—we'd love to meet you. The Opportunity We're looking for a seasoned Fractional General Counsel to serve as Sleep Doctor's senior legal and compliance leader. This is a hands-on, high-ownership role for an attorney who thrives in fast-moving environments and wants to make a real difference—not just advise from the sidelines. You'll own our end-to-end compliance function, serve as a trusted strategic partner to the executive team, and dramatically reduce our reliance on outside counsel by bringing sharp, practical legal judgment in-house. This is the right role if you want to build something meaningful at a company that's reshaping the future of sleep health. What You'll Own Compliance Program Leadership <ul data-path-to-node="17"> <li> Design, implement, and continuously improve a comprehensive compliance program spanning DME, telehealth, and digital health operations. </li> <li> Serve as the company's Compliance Officer, maintaining all relevant policies, procedures, and training programs across the business. </li> <li> Conduct and oversee internal compliance audits; manage any regulatory inquiries or investigations. </li> <li> Monitor evolving federal and state regulatory requirements and translate them into operational guidance for the business. </li> </ul> Healthcare Regulatory <ul data-path-to-node="20"> <li> Own legal and regulatory matters related to our telehealth platform and DME supply and billing operations, including CMS/Medicare, Medicaid, and state-level requirements. </li> <li> Advise on licensure requirements across all 50 states as we scale, with particular focus on the patchwork of telehealth practice standards and DME supplier licensing that varies significantly by jurisdiction. </li> <li> Partner closely with clinical and operations teams to ensure care delivery models remain compliant as the business evolves. </li> </ul> Data Privacy & Security <ul data-path-to-node="23"> <li> Lead HIPAA compliance enterprise-wide, including Business Associate Agreement management, PHI/PII handling, breach response protocols, and workforce training. </li> <li> Oversee compliance with applicable state privacy laws (CCPA, Washington My Health My Data Act, and others). </li> <li> Partner with our technology and product teams on privacy-by-design practices for our digital health products. </li> </ul> Commercial & Employment Law <ul data-path-to-node="26"> <li> Negotiate and manage key commercial contracts—partner agreements, vendor agreements, strategic partnership structures—with minimal outside counsel involvement. </li> <li> Serve as first-line legal resource for employment law questions, working in close partnership with HR on hiring, separation, policy, and employee relations matters. </li> <li> Support the CFO and executive team on governance matters, including board materials and delegation of authority frameworks. </li> </ul> Strategic Partnership & Business Development Support <ul data-path-to-node="29"> <li> Provide legal support on strategic partnerships, including government and federal program relationships (e.g., VA partnerships). </li> <li> Advise on deal structuring, term sheet review, and contract negotiation for growth initiatives. </li> </ul> What We're Looking For Required <ul data-path-to-node="34"> <li> J.D. from an accredited law school; active bar membership in at least one U.S. jurisdiction. </li> <li> 10+ years of legal experience, with substantial in-house or law firm experience in healthcare law. </li> <li> Deep expertise in DME (Durable Medical Equipment) regulations, including Medicare/Medicaid billing and compliance. </li> <li> Hands-on telehealth regulatory experience across multiple states. </li> <li> Demonstrated ownership of a compliance program—you've built or run one, not just advised on one. </li> <li> Comprehensive knowledge of HIPAA, PHI/PII handling, and healthcare data privacy. </li> <li> Proven ability to function as a resourceful, independent operator in a startup or scaling-stage business. </li> <li> Track record of materially reducing outside counsel spend by handling matters in-house. </li> </ul> Strongly Preferred <ul data-path-to-node="37"> <li> Experience in digital health or health tech—comfortable navigating the intersection of technology, consumer products, and regulated healthcare services. </li> <li> Familiarity with FTC regulations applicable to health claims and consumer-facing digital health content. </li> <li> Experience supporting government program partnerships (VA, CMS, etc.). </li> <li> Prior experience as a fractional, embedded, or sole in-house counsel. </li> </ul> What Success Looks Like In your first 90 days, you'll have assessed our current compliance posture, prioritized a near-term remediation roadmap, and established yourself as the go-to legal voice for the leadership team. Within six months, you'll own end-to-end compliance, have meaningfully reduced our outside counsel spend, and be a trusted strategic partner on our most important commercial and regulatory decisions. Why Sleep Doctor <ul data-path-to-node="45"> <li> Mission-driven company with real clinical impact—we help people sleep better and live healthier lives. </li> <li> Lean, high-trust executive team that values substance over process. </li> <li> Opportunity to grow with the organization—this role is built to expand as we do. </li> <li> Flexible fractional structure with meaningful ownership and visibility. </li> </ul> Compensation <ul data-path-to-node="49"> <li> ~$300-350/hour | 20-30 hours/week </li> <li> This is a fractional engagement with potential to grow into a broader role as the company scales. </li> </ul> </div> </div> </div> Sleep Doctor is committed to bringing together individuals from diverse backgrounds and perspectives. We strive to create an inclusive environment where everyone can thrive and be their authentic self, feel a sense of community, and do great work together. We are proud to be an equal opportunity employer open to all qualified applicants.

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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...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

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...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

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...

DISCLAIMER

Other Jobs To Apply

Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

5. HOW DO YOU PROCESS INFORMATION?

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

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

8. HOW TO PRIORITIZE WORK?

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

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