VP Sales: Medicare & ACA Marketplace

Join Us! HealthCare.com has become one of America’s fastest-growing insurtech companies, revolutionizing how consumers shop for health insurance. Leveraging advanced technology and data science, the company has developed customized proprietary products to better fit consumer requirements, enhance customer satisfaction, and take some of the guesswork and inefficiencies out of buying insurance. The Opportunity  Healthcare.com operates a high-growth, technology-driven marketplace at the intersection of consumer intent and insurance distribution. We don’t just generate leads; we facilitate the most critical connection in the healthcare journey: matching high-intent consumers with the right Medicare and ACA solutions.  As our Sales Leader, you will be the primary architect of our revenue growth. This isn’t just a management role — it’s an invitation to leverage your deep industry ties and executive presence to scale a two-sided marketplace that empowers consumers and drives massive ROI for our partners.  Executive Impact & Key Responsibilities  Revenue Growth & Market Expansion  •  Scale the ecosystem by securing high-value purchasing agreements with Medicare Advantage, Medicare Supplement, PDP, and ACA agency partners.  •  Structure and negotiate sophisticated performance contracts including CPL, CPA, and inbound call-based models.  •  Identify emerging distribution opportunities within the Medicare and ACA ecosystems.  Relationship Management & Brand Advocacy  •  Build executive-level relationships with agencies, call centers, aggregators, and carriers. Act as a trusted advisor on lead strategy and growth optimization.  •  Evangelize the Healthcare.com Edge: proprietary consumer acquisition strategy, data-driven intent signals, and compliance-first marketing approach.  •  Represent Healthcare.com at industry conferences, carrier events, and networking forums.  Sales Leadership & Operations  •  Develop and execute a comprehensive sales strategy aligned with company-wide growth targets at $100M+ revenue scale.  •  Build, mentor, and lead a high-performing sales team with a culture of accountability and continuous improvement.  •  Partner cross-functionally with Marketing, Compliance, and Operations to ensure compliant, scalable enrollment opportunities.    Professional Qualifications  Required Experience  •  7–10+ years of sales leadership in the Medicare and/or ACA markets.  •  Proven success selling insurance leads, inbound calls, or performance marketing solutions (CPL/CPA models).  •  Extensive existing relationships with decision-makers at MA and ACA agencies, FMOs, and high-volume call centers.  •  Strong understanding of CMS regulations, TCPA, and healthcare marketing compliance.    Core Competencies  •  Exceptional negotiation skills with the ability to close complex, high-stakes deals with C-suite stakeholders.  •  Comfortable reviewing performance metrics, ROI reporting, and data-driven business models.  •  Strategic agility: ability to pivot between high-level strategy and hands-on deal execution.  •  Elite written and verbal communication skills.    Preferred  •  Experience within a two-sided marketplace or lead-generation platform.  •  Background in digital performance marketing and consumer journey optimization.  •  Experience scaling sales operations driving revenue in the $50M–$250M+ range.    What Success Looks Like  •  Significant growth in monthly recurring revenue from both new and existing Medicare/ACA partners.  •  High retention rates and increased share of wallet from top-performing agencies.  •  Healthcare.com established as the premium driver of distributor customer acquisition success.