1. Twentyeight Health

Twentyeight Health (www.twentyeighthealth.com) is a mission-driven women's health platform that provides telemedicine, medication delivery and care coordination in Spanish and English. Our vision is to address health equity by providing high quality, convenient and affordable women’s health services designed to be inclusive of underserved communities.

Today, we are active in 47 states, and have exciting growth plans. We are rapidly expanding our offerings, and we are backed by some of the best healthcare & consumer investors pioneering digital health including Third Prime, Town Hall Ventures, SteelSky Ventures, RH Capital, Seae Ventures and GingerBread Capital, and more.

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You’ll be joining a dynamic, supportive and mission-driven environment. We are a team of doctors, public health experts, designers, engineers and builders across the US committed to changing the face of healthcare, particularly for underserved communities.

At Twentyeight Health, we value a diverse workplace and strongly encourage women, BIPOC, LGBTQ+ individuals, people with disabilities, members of ethnic minorities, foreign-born residents, and veterans to apply. We are committed to fostering a culture of mutual respect, diversity and inclusion for our employees and customers alike and we can’t wait for you to be a part of it.

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2. Role

We are looking for an experienced Medical Director to build and lead the clinical team that is at the heart of Twentyeight Health's mission. Our providers are our product—they're who our patients come to for judgment-free consultations, compassionate listening, expert education, and convenient care. In this strategic leadership role, you will hire exceptional providers, set clinical standards, serve as the collaborating physician for our Nurse Practitioners, and shape the clinical vision that enables us to deliver outstanding care to women across the country. You'll partner closely with our Clinical Lead (NP) who handles day-to-day provider coaching, allowing you to focus on building a world-class clinical team, maintaining the highest standards of care, and scaling our impact.

You'll spend approximately 50% of your time seeing patients yourself to stay connected to the patient experience and model the clinical excellence we expect from every provider. This is a rare opportunity to directly shape how millions of women access reproductive healthcare by leading and scaling the clinical team that makes it possible. The ideal candidate brings clinical expertise in women's health, experience with multi-state collaborative practice, exceptional hiring judgment, and the entrepreneurial drive to scale a mission-driven startup.

This is a 1099 contractor role associated with Medical Professional Corporations that Twentyeight Health provides administrative services for. The role requires willingness to serve as a Professional Corporation (PC) owner.

3. Manager

You will report to our COO, Mara Castro.

4. Responsibilities

• Clinical Leadership & Strategy
  
  • Set the clinical vision and standards for Twentyeight Health's provider network, ensuring evidence-based, patient-centered care across all services
  • Develop clinical protocols, guidelines, and workflows—leading the process of getting provider input and buy-in
  • Serve as the clinical authority for complex cases, escalations, and regulatory/compliance matters
  • Monitor clinical quality metrics and partner with Clinical Lead to identify trends and improvement opportunities
• Collaborative Agreements & Multi-State Oversight
  
  • Serve as the collaborating physician for Nurse Practitioners requiring collaborative agreements in accordance with state-specific regulations
  • Review and co-sign charts as required by state collaborative practice agreements
  • Maintain active medical licenses in states where collaborative agreements or medical oversight is required
  • Stay current on evolving state regulations regarding NP practice and ensure compliance across the provider network
• Provider Hiring, Onboarding & Performance Management
  
  • Own the full hiring process: define role requirements, conduct interviews, make hiring decisions, and extend offers
  • Ensure Clinical Lead is equipped to lead comprehensive provider onboarding for clinical and operational readiness
  • Partner with Clinical Lead on performance management: Clinical Lead handles day-to-day coaching and metric improvement; you handle formal performance reviews, PIPs, and termination decisions
  • Identify and flag licensing, credentialing, or scope-of-practice needs proactively in partnership with operations team
• Clinical Practice
  
  • Maintain an active patient panel (~50% of clinical time) to stay close to our users and model best-in-class care
• Team Culture & Cross-Functional Leadership
  
  • Build a positive, mission-driven clinical culture where providers feel supported, valued, and connected to our purpose while establishing clear performance expectations
  • Partner closely with COO, Clinical Lead, and Clinical Operations team to align clinical strategy with business objectives
  • Represent the clinical voice in executive conversations, surfacing frontline insights that shape organizational priorities

5. Requirements

• MD or DO degree licensed nationwide
• 5+ years of clinical experience, preferably in women's health, family medicine, or primary care
• 2+ years of leadership experience including hiring, managing, and developing clinical teams
• Willingness to serve as a Professional Corporation (PC) owner and collaborative physician for multiple Nurse Practitioners
• Proven ability to develop and implement clinical guidelines and quality improvement initiatives
• Strong hiring judgment and experience building high-performing teams
• Comfort making difficult personnel decisions (performance management, terminations) with fairness and professionalism
• Excellent communication skills with ability to engage, motivate, and support diverse clinical teams
• Thrives in fast-paced, evolving startup environments; can balance structure with flexibility
• Preferred:

• Experience in telehealth or multi-state virtual care model
• Background in women's reproductive or sexual health
• Familiarity with value-based care, quality metrics, or performance management
• Previous startup or high-growth company experience
• Experience managing managers or leading through others

6. Attributes We Look For

• Strategic thinker with execution skills: You can set the vision AND make it happen
• Strong hiring instincts: You know how to identify, attract, and select top clinical talent
• Accountability-focused: You set clear expectations and hold yourself and others to high standards
• Empathetic but decisive: You care deeply about people while making tough decisions when needed
• Data-informed: You use metrics and evidence to guide clinical and management decisions
• Mission-driven: You're passionate about expanding access to women's healthcare
• Collaborative leader: You build strong partnerships across functions and empower others to lead
• Continuous learner: You seek feedback, iterate quickly, and model growth mindset
  
  

7. Our cultural values

• Our mission is our north star, providing high quality healthcare to underserved women
• We treat people with care, including team members, our users, clinician partners, and pharmacy partners
• We hold ourselves to high standards
• We create an environment where people can show up as their authentic and best selves
• We have a growth mindset fueled by curiosity, openness to feedback, and focus on constant improvement

8. Compensation & Benefits

• Hourly rate $150
• Expected hours 20-40 weekly within 9am-5pm ET
• Malpractice coverage and additional licensure support
• Admin support - so you can focus on clinical care
• Fun team events & a chance to network with healthcare professionals

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9. How to apply

Please complete the application form and upload your resume here. Thank you for your interest, and we look forward to reviewing your application!