Strategic Partnerships Director, Medicaid

Pomelo Care is the leading virtual medical practice for women and children, providing care across pregnancy, postpartum, pediatrics, menopause, and perimenopause. We combine proactive, 24/7 clinical care with technology that helps us reach patients earlier, identify risks sooner, and deliver personalized care throughout their journey. Our team includes clinicians, technologists, operators, and problem-solvers working together to make high-quality care more accessible for families nationwide.

About The Role:

Your north star: Drive topline revenue growth for Pomelo Care by building and expanding partnerships with Medicaid health plans.

As a Strategic Partnerships Director on the Medicaid team you will be responsible for sourcing, managing, negotiating and closing deals with health plans. This role is built for people who are passionate about improving outcomes in women’s and children’s health, and deeply understand how to navigate Medicaid MCOs.

This role reports to the VP of Medicaid Partnerships and is open to any candidates located in the continental US.

What you'll do:

• Own the full sales cycle - from conference networking and outreach to leading sales calls to structuring contracts and closing deals

• Build and manage a robust pipeline of Medicaid health plan opportunities

• Navigate complex stakeholder environments, building relationships with C-suite executives, VP-level champions and operational decision makers

• Develop compelling presentations, proposals and ROI frameworks tailored to each plan’s priorities

• Analyze pipeline data and continuously refine go-to-market processes to improve win rates and shorten cycles

• Travel to conferences and in-person meetings to build trusted relationships with health plan leaders - Q1 and Q2 travel ~25%, Q3 and Q4 ~50%

Who you are:

Experience and Skills

• 5+ years of experience in an enterprise sales, growth, or business development role, with at least 2 years of experience selling into health plans

• Demonstrated track record of closing complex deals $500k-$1M+ ACV

• Deep understanding of health plan priorities - you know how to identify economic buyers, decision makers, influencers and how to navigate deals with 20+ stakeholders

• Energized by the autonomy and scope of working at a growth-stage company that is scaling rapidly

How You Work

• Top-tier grit and resilience - health plan sales cycles are long and competitive; you know how to stay in the game

• Exceptional written and verbal communication skills - you can distill complexity into clear, simple messaging

• Resourceful - you move fast, improvise well, and don’t wait to be handed a playbook

• Coachable - you ask good questions, learn constantly, and welcome direct feedback

• Metrics-oriented - you track your pipeline with discipline and use data to prioritize your time

• On the road - you are excited to travel to conferences every week in Q3 and Q4, and be on the ground meeting with health plans throughout the year

 What Drives You

• Passionate about improving women’s and children’s health outcomes in Medicaid

• Being a top performer on team that is obsessed with winning

• Operating in an ambiguous environment

• Working at the intersection of healthcare and technology

Why you should join our team

By joining Pomelo, you will get in on the ground floor of a fast-moving, well-funded, and mission-driven startup that always puts the patient first. You will learn, grow and be challenged, and have fun with your team while doing it.

We strive to create an environment where employees from all backgrounds are respected. We value working across disciplines, moving fast, data-driven decision making, learning, and always putting the patient first.

Benefits and Perks:

• Comprehensive Health, Dental, and Vision coverage for employees and their families

• High deductible Health Plans with Health Savings Account (HSA) options

• Flexible Spending Account (FSA)

• Equity grant participation

• 401(k) program 

• Competitive vacation policy 

• 16 weeks paid parental leave 

• Fully remote work flexibility (within the US)

Compensation:

The expected base salary range for this role is $165,000-$185,000. This role is also eligible for variable compensation, with expected on-target earnings of $330,000 to $370,000, and equity, giving you an ownership stake in Pomelo’s mission. Actual compensation may vary based on relevant experience, skills, competencies, and certifications.

At Pomelo, we are committed to hiring the best team to improve outcomes for all mothers and babies, regardless of their background. We need diverse perspectives to reflect the diversity of problems we face and the population we serve. We look to hire people from a variety of backgrounds, including but not limited to race, age, sexual orientation, gender identity and expression, national origin, religion, disability, and veteran status.

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