VP of Mid-Market & Navigation Sales

VP of Mid-Market & Navigation Sales

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 (

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.

• Build and lead the
• Own the end-to-end commercial strategy and execution for Care Navigation.
• Lead the Strategic Partnerships subteam, optimizing channel and navigation synergies for the
• 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.

• Sales leadership excellence : 5+ years of progressive sales leadership experience in the small to mid-market segment (
• 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.

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

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

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 satellite offices in Denver and…