VP, Sales – Employer & TPA Segment

The Vice President of Sales – Employer & TPA Segment will be a foundational market leader responsible for establishing MacroHealth’s presence and credibility within the employer and Third-Party Administrator (TPA) ecosystem. This role combines strategic market development, thought leadership, and enterprise sales execution to shape how MacroHealth enters and scales in this new segment.

This is a high-impact, player-coach opportunity for an experienced commercial leader who thrives in building new markets—someone who brings deep industry credibility, understands the complex dynamics of self-funded healthcare, and can translate market insights into actionable go-to-market (GTM) and product strategies. Early success will be defined by your ability to inspire trust, evangelize MacroHealth’s capabilities, and bring the organization along on the journey toward long-term market success.

The ideal candidate will have extensive experience leading and closing large, complex enterprise deals—the kind that transform client operations and shape strategic relationships for years to come.

Sales Leadership • Product • Marketing • Legal • Finance • Senior Leadership • Customer Operations

• Lead MacroHealth’s entry into the Employer & TPA ecosystem, establishing brand credibility and trusted relationships across the segment.

• Serve as the voice of the market internally—educating teams on customer needs, buying dynamics, and evolving trends.

• Partner with Marketing and Product to shape the go-to-market strategy and product roadmap based on real-time feedback from the field.

• Develop a near- and long-term market penetration plan that balances early wins with sustainable growth.

• Drive initial commercial success by identifying, engaging, and closing large, complex enterprise opportunities with self-insured employers, TPAs, and benefits consultants.

• Lead the full enterprise sales cycle—from prospecting through contracting—with tailored approaches for each segment.

• Build and manage a high-value pipeline focused on deals that meaningfully advance MacroHealth’s market position and revenue growth.

• Over time, scale and mentor a small team of sales professionals focused on this segment.

• Collaborate with Product, Marketing, and Strategy to develop the narratives, tools, and solution constructs needed to compete and win large enterprise contracts.

• Represent MacroHealth as a credible, trusted partner within the employer and TPA communities.

• Engage with benefits leaders, consultants, and industry associations to position MacroHealth as a thought leader in healthcare cost optimization and transparency.

• Contribute to industry events, panels, and forums that elevate the company’s visibility and influence.

• Develop long-term relationships that lead to strategic, multi-year partnerships and sustainable revenue streams.

• Work collaboratively across departments to ensure market learnings are translated into actionable insights.

• Partner with Product and Strategy to shape solution design and commercialization priorities.

• Guide Marketing in developing content, positioning, and campaigns aligned to employer and TPA buyer personas.

• Provide feedback to Legal and Finance to ensure deal structures align with large-scale enterprise contracting requirements.

• Lead complex deal negotiations with a focus on value creation, scalability, and long-term client success.

• Partner with Legal and Finance to structure agreements that support both short-term growth and sustainable strategic partnerships.

• Deep understanding of self-funded employer healthcare, TPA business models, and the broader healthcare benefits ecosystem.

• Proven ability to build new markets or segments and influence internal strategy and GTM plans.

• Demonstrated success in closing large, complex, multi-stakeholder enterprise deals in healthcare or benefits-related markets.

• Exceptional relationship-building, influencing, and storytelling skills with executive audiences.

• Ability to synthesize market feedback into strategic recommendations for Product and Leadership.

• Entrepreneurial mindset—comfortable with ambiguity, energized by creation and growth.

• Executive presence with the credibility to represent MacroHealth in the market and within the organization.

• Bachelor’s degree or equivalent experience required.

• Minimum of 10 years of enterprise sales experience, including at least 5 years selling into employer benefits, TPA, or healthcare network environments.

• Experience shaping go-to-market strategies or launching new segments within healthcare strongly preferred.

• Proven track record of closing high-value, multi-million-dollar enterprise contracts.

• Prior experience in healthcare cost containment, network optimization, or data-driven benefit solutions preferred.

• Experience building and leading teams during early market development phases is a plus.

Travel as required to support client engagement, market development, and industry events.

$180-200k annual base salary plus commission, equity, 401(k) match, flexible PTO, and comprehensive health benefits (medical, dental, vision).

One Team

• Act as one team with fellow MacroMates and customers.

• Value humility, collaboration, and shared success.

• Maintain an “All for One, One for All” attitude.

Deliver on Promises

• Do the right thing.

• Follow through with integrity and transparency.

• Work with urgency and accountability.

Macro Thinking

• Think boldly and into the future.

• Lead with curiosity and a growth mindset.

• Serve as a thought leader shaping the future of healthcare.