VP of Mid-Market & Navigation Sales

ABOUT THE ROLE:

The VP of Mid-Market & Navigation Sales will be responsible for building Rightway’s small business and mid-market PBM go-to-market function and leading significant revenue growth for the business over the next few years. This role will also own the commercial strategy and execution for our Care Navigation solution and lead the Strategic Partnerships team, a critical growth lever for both our care navigation and PBM business.

This leader will build and lead Rightway's expansion into the small business and mid-market PBM segments (<5k enrolled lives), representing nearly 50% of the total self-funded market that remains largely untapped by innovative PBMs.

This is a complex, high-impact opportunity requiring a seasoned executive who combines strategic vision, executional rigor, and a builder’s mindset. Success in this role will require defining the playbook for selling innovative healthcare benefits to smaller self-funded employers—something no one has yet done at scale.

You will report directly to the Chief Commercial Officer and work closely with senior leadership, including the CEO, EVP of Growth, and VP of Strategic Partnerships, to shape and execute our market strategy.

WHAT YOU’LL DO:

• Build and lead the <5k life PBM sales function to deliver significant revenue in 2026 and beyond.
• Own the end-to-end commercial strategy and execution for Care Navigation.
• Lead the Strategic Partnerships subteam, optimizing channel and navigation synergies for the <5k market.
• Develop and manage a team of 11+ FTEs.
• Design and operationalize scalable, repeatable sales processes to efficiently sell a very high volume of RFPs and opportunities across your team.
• Partner with Marketing, Product, Implementation, and Customer Success to ensure cohesive go-to-market execution.
• Serve as executive sponsor for key partnerships and high-value client opportunities.
• Analyze and report sales performance using Salesforce and other tracking tools.
• Represent Rightway at major industry events, conferences, and trade shows.

WHO YOU ARE:

• Sales leadership excellence: 5+ years of progressive sales leadership experience in the small to mid-market segment (<5,000 lives), with demonstrated expertise in developing and managing strategic channel partnerships as a core revenue driver.
• Proven Growth Track Record: Documented success scaling small group sales to achieve 100%+ year-over-year net new revenue growth through strategic execution and market expansion.
• People leadership excellence: 3+ years leading teams of top tier sellers
• Process Architecture & Scalability: Hands-on experience designing, implementing, and optimizing scalable sales processes, organizational structures, and go-to-market strategies from the ground-up, with measurable impact on team productivity and revenue outcomes.
• Strategic Problem-Solving: Exceptional analytical and critical thinking capabilities combined with intellectual agility to navigate complex market challenges, adapt to evolving business needs, and drive innovative solutions in fast-paced environments.
• Execution & Resilience: Demonstrated grit and relentless execution mindset with a proven ability to overcome obstacles, meet aggressive targets, and maintain high performance standards under pressure.
• Cross-Functional Leadership: Strong collaborative leadership style with experience building consensus across diverse teams (Marketing, Operations, Product, Customer Success) to drive unified business objectives and optimize customer experience.
• Bachelor’s degree required; graduate degree preferred (e.g., MBA).
• Willing to travel nationally.

IDEAL:

• Track record of consistent President’s Club achievement in PBM or healthcare benefits sales.
• Experience driving results through both direct and channel sales models.

COMPENSATION:

Base Salary: $225,000 - $250,000

CYBERSECURITY AWARENESS NOTICE

In response to ongoing and industry-wide fraudulent recruitment activities (i.e., job scams), Rightway wants to inform potential candidates that we will only contact them from the @rightwayhealthcare.com email domain. We will never ask for bank details or deposits of any kind as a condition of employment. If you have any questions about a suspicious interaction with Rightway, please feel free to reach out to us at [email protected].

ABOUT RIGHTWAY:

Rightway is on a mission to harmonize healthcare for everyone, everywhere. Our products guide patients to the best care and medications by inserting clinicians and pharmacists into a patient’s care journey through a modern, mobile app. Rightway is a front door to healthcare, giving patients the tools they need along with on-demand access to Rightway health guides, human experts that answer their questions and manage the frustrating parts of healthcare for them.

Since its founding in 2017, Rightway has raised over $200mm from investors including Khosla Ventures, Thrive Capital, and Tiger Global. We’re headquartered in New York City, with a satellite offices in Denver and Dallas. Our clients rely on us to transform the healthcare experience, improve outcomes for their teams, and decrease their healthcare costs.

HOW WE LIVE OUR VALUES TO OUR TEAMMATES:

We’re seeking those with passion for healthcare and relentless devotion to our goal. We need team members that embody our following core values:

1) We are human, first
Our humanity binds us together. We bring the same empathetic approach to every individual we engage with, whether it be our members, our clients, or each other. We are all worthy of respect and understanding and we engage in our interactions with care and intention. We honor our stories. We listen to—and hear—each other, we celebrate our differences and similarities, we are present for each other, and we strive for mutual understanding.

2) We redefine what is possible
We always look beyond the obstacles in front of us to imagine new solutions. We approach our work with inspiration from other industries, other leaders, and other challenges. We use ingenuity and resourcefulness when faced with tough problems.

3) We debate then commit
We believe that a spirit of open discourse is part of a healthy culture. We understand and appreciate different perspectives and we challenge our assumptions. When working toward a decision or a new solution, we actively listen to one another, approach it with a “yes, and” mentality, and assume positive intent. Once a decision is made, we align and champion it as one team.

4) We cultivate grit
Changing healthcare doesn’t happen overnight. We reflect and learn from challenges and approach the future with a determination to strive for better. In the face of daunting situations, we value persistence. We embrace failure as a stepping stone to future success. On this journey, we seek to act with guts, resilience, initiative, and tenacity.

5) We seek to delight
Healthcare is complicated and personal. We work tirelessly to meet the goals of our clients while also delivering the best experience to our members. We recognize that no matter the role or team, we each play a crucial part in our members’ care and take that responsibility seriously. When faced with an obstacle, we are kind, respectful, and solution-oriented in our approach. We hold ourselves accountable to our clients and our members’ success.

Rightway is PROUDLY an Equal Opportunity Employer that believes in strength in the diversity of thought processes, beliefs, background and education and fosters an inclusive culture where differences are celebrated to drive the best business decisions possible. We do not discriminate on any basis covered by appropriate law. All employment is decided on the consideration of merit, qualifications, need and performance.