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VP Sales: Medicare & ACA Marketplace

3 weeks ago
Anywhere
Full-time
Executive
Head of Sales
Sales and Business Development
Apply Now
Healthcare.com

Healthcare.com

HealthCare.com is a leading internet startup providing health insurance quotes and a search engine for healthcare consumers, helping users analyze and choose from a wide range of health insurance options.

Internet Software & Services
11-50
Founded 2006
$244M raised
View All Jobs 5

Description

  • Scale the marketplace by securing high-value purchasing agreements with Medicare Advantage, Medicare Supplement, PDP, and ACA agency partners.
  • Structure and negotiate performance-based contracts, including CPL, CPA, and inbound call models.
  • Identify emerging distribution opportunities within the Medicare and ACA ecosystems.
  • Build executive-level relationships with agencies, call centers, aggregators, and carriers.
  • Act as a trusted advisor on lead strategy and growth optimization for partners.
  • Represent Healthcare.com at industry conferences, carrier events, and networking forums.
  • Develop and execute a sales strategy aligned with company growth targets at the $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 support compliant and scalable enrollment opportunities.

Requirements

  • 7–10+ years of sales leadership experience in the Medicare and/or ACA markets.
  • Proven success selling insurance leads, inbound calls, or performance marketing solutions using 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.
  • Exceptional negotiation skills with the ability to close complex, high-stakes deals with C-suite stakeholders.
  • Ability to review performance metrics, ROI reporting, and data-driven business models.
  • Strategic agility to move between high-level planning and hands-on deal execution.
  • Excellent written and verbal communication skills.
  • Experience in a two-sided marketplace or lead-generation platform is preferred.
  • Background in digital performance marketing and consumer journey optimization is preferred.
  • Experience scaling sales operations in the $50M–$250M+ revenue range is preferred.

Benefits

  • Work from home in a fully remote role.
  • Medical, dental, and vision insurance.
  • Up to 15 days of paid time off.
  • 12 company-observed holidays.
  • 401(k) plan with company match.
  • Life insurance.
  • Professional growth opportunities.
  • Inclusive company culture and excellent work environment.

Interested in this position?

Apply directly on the company website

Apply Now

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