[Hiring] VP Sales: Medicare & ACA Marketplace @HealthCare

Role Description

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. You will evangelize a data-driven model that prioritizes compliance, quality, and performance-based results.

• Revenue Growth & Market Expansion
  • Drive aggressive new revenue growth by securing high-value purchasing agreements with Medicare Advantage, Medicare Supplement, PDP, and ACA agency partners.
  • Structure and negotiate sophisticated performance contracts, including CPL (Cost Per Lead), CPA (Cost Per Acquisition), and inbound call-based models.
  • Uncover and capture emerging distribution opportunities within the Medicare and ACA ecosystems to stay ahead of market shifts and enrollment cycles.
• Relationship Management & Brand Advocacy
  • Build and maintain executive-level relationships with agencies, call centers, aggregators, and carriers. Act as a trusted advisor on lead strategy and growth optimization.
  • Clearly articulate the "Healthcare.com Edge," including our proprietary consumer acquisition strategy, data-driven intent signals, and compliance-first marketing approach.
  • Represent Healthcare.com at industry conferences, carrier events, and networking forums to maintain high visibility and credibility.
• Sales Leadership & Operations
  • Develop and execute a comprehensive sales strategy aligned with company-wide growth targets and $100M+ revenue scales.
  • Build, mentor, and lead a high-performing sales team, fostering a culture of accountability, deal-making expertise, and continuous improvement.
  • Partner with Marketing, Compliance, and Operations to ensure our traffic converts into scalable, compliant enrollment opportunities for our partners.

Qualifications

• 7–10+ years of sales leadership experience specifically within the Medicare and/or ACA markets.
• Demonstrated success selling insurance leads, inbound calls, or performance marketing solutions (CPL/CPA models).
• Extensive existing relationships with decision-makers at Medicare Advantage and ACA agencies, FMOs, and high-volume call centers.
• Strong understanding of CMS regulations, TCPA considerations, and healthcare marketing compliance standards.

Requirements

• Exceptional negotiation skills with the ability to close complex, high-stakes deals with CEOs and high-level stakeholders.
• Comfortable reviewing performance metrics, ROI reporting, and data-driven business models to prove value to partners.
• Ability to pivot between high-level strategy and hands-on deal execution without losing momentum.
• Elite written and verbal communication skills; ability to explain complex marketplace dynamics simply and persuasively.

Preferred Qualifications

• Experience working 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.

Benefits

• Opportunity to work from home
• Excellent work environment
• Medical, dental, and vision insurance
• Up to 15 days of paid time off
• 11 company observed holidays
• 8 weeks of paid parental leave
• 401k plan with company match
• Life insurance
• Professional growth opportunity
• Inclusive company culture established by an incredible team!