General Counsel (Fractional) - Job Description

About Us Sleep Doctor helps millions get a full night's rest across our brands—SleepDoctor.com, SleepFoundation.org, and SleepApnea.org—combining clinical expertise with consumer-first experiences to help people understand their sleep, tackle real challenges, and wake up to healthier lives. ~20-30 Hours/Week.

The Opportunity A seasoned Fractional General Counsel to serve as Sleep Doctor's senior legal and compliance leader. This hands-on, high-ownership role owns end-to-end compliance, serves as a trusted strategic partner to the executive team, and reduces reliance on outside counsel by bringing sharp, practical legal judgment in-house.

What You'll Own

• Compliance Program Leadership: Design, implement, and continuously improve a comprehensive compliance program spanning DME, telehealth, and digital health operations. Act as Compliance Officer, maintaining policies, procedures, and training across the business. Conduct and oversee internal compliance audits; manage regulatory inquiries or investigations. Monitor evolving federal/state regulatory requirements and translate into operational guidance.
• Healthcare Regulatory: Manage legal/regulatory matters related to telehealth platform and DME supply/billing (CMS/Medicare, Medicaid, state requirements). Advise on licensure across all 50 states; ensure care delivery models remain compliant as the business evolves. Collaborate with clinical/operations teams.
• Data Privacy & Security: Lead HIPAA compliance enterprise-wide, manage Business Associate Agreements, PHI/PII handling, breach response, workforce training; oversee state privacy laws (CCPA, Washington My Health My Data Act, etc.); partner with tech/product on privacy-by-design.
• Commercial & Employment Law: Negotiate/manage key commercial contracts with minimal outside counsel; serve as first-line employment law resource; partner with HR on hiring, separation, policy, employee relations. Support governance matters with CFO/executive team (board materials, delegation of authority).
• Strategic Partnership & BD Support: Provide legal support on strategic partnerships (government/federal programs like VA); advise on deal structuring, term sheets, and contract negotiation for growth initiatives.

What We're Looking For

• Required: J.D. from an accredited law school; active bar in at least one U.S. jurisdiction. 10+ years of legal experience (in-house or law firm) in healthcare law. Deep DME regulatory expertise (Medicare/Medicaid billing and compliance). Hands-on telehealth regulatory experience across multiple states. Proven track record building/running a compliance program. Comprehensive HIPAA/PHI/PII knowledge. Ability to operate independently in a startup or scaling environment. Demonstrated reduction of outside counsel spend.
• Strongly Preferred: Experience in digital health/health tech; familiarity with FTC health-claims regulations; experience supporting government program partnerships (VA, CMS); prior fractional/embedded/sole in-house counsel experience.

What Success Looks Like

• First 90 days: Assess current compliance posture, set near-term remediation roadmap, establish yourself as the go-to legal voice for leadership.
• Within six months: Own end-to-end compliance, meaningfully reduce outside counsel spend, be a trusted strategic partner on key commercial/regulatory decisions.

Why Sleep Doctor

• Mission-driven company with real clinical impact; supportive executive team valuing substance over process.
• Opportunity to grow with the organization; role is built to expand as the company scales.
• Flexible fractional structure with meaningful ownership and visibility.
• Compensation: $300-350/hour | 20-30 hours/week; potential to grow into broader role.

Who You Are

• Motivated general counsel with a practical, in-house mindset and a track record of building strong compliance and regulatory programs in healthcare/digital health settings.
• Strategic partner to executive leadership, capable of advising on complex regulatory and operational issues while driving initiatives forward.