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.
Head of Distribution
Healthcare.com operates one of the fastest-growing two-sided insurance marketplaces in the country, connecting over 20 million consumers annually with trusted distribution partners. Our platform enables agencies, carriers, FMOs, call centers, and marketing organizations to acquire high-intent consumers across Medicare, ACA, Alternative ACA, ancillary, and life products through a transparent, performance-based bidding environment.
We are looking for a Head of Distribution who is equal parts operator, relationship-builder, and closer. You’ll step into a business with real momentum and be responsible for scaling it into a high-performing, market-leading distribution engine.
This is a fast-moving, high-accountability environment where people take ownership and drive outcomes. There’s no unnecessary bureaucracy—just a team focused on building and winning together.
This is not a traditional carrier-side role. You’re not pushing a single product—you’re building a marketplace where partners invest and grow based on performance. And this is not an escalation role—you’ll build the systems and teams so the business runs without depending on you.
What You’ll Lead
You’ll lead three core functions—Sales, Partner Solutions, and B2B Marketing—and bring them together into one cohesive distribution engine. The foundation is in place. Your job is to sharpen it, scale it, and make it perform.
Sales
● Build and lead a high-performing sales team focused on acquiring the right partners
● Use your network to open doors and accelerate pipeline
● Lead and close high-value partnerships (CPL, CPA, inbound call models)
● Bring structure to pipeline management, forecasting, and execution
Partner Solutions
● Build a team that helps partners succeed and grow—not just support them
● Drive partner retention, performance, and increased spend over time
● Create clear ownership and processes so partners have a consistent experience
● Develop playbooks to onboard, optimize, and grow partner relationships
B2B Marketing
● Build the marketing engine that drives inbound demand
● Establish Healthcare.com as a trusted brand in insurance distribution
● Lead content, thought leadership, and conference strategy
● Align closely with Sales and Partner Solutions to support growth
What You Bring
● 7+ years of experience in insurance distribution, lead generation, or marketplace-based acquisition
● Strong understanding of Medicare, ACA/Alternative ACA, and ancillary products—you know how this ecosystem works
● A real network across agencies, FMOs, call centers, carriers, and partners—and the ability to turn those relationships into revenue
● Experience building and leading teams across sales, account management, or partner solutions
● A track record of closing meaningful partnerships and growing partner spend over time
● Experience working in performance-based environments (CPL, CPA, marketplace models, etc.)
● Comfortable using data to make decisions and improve outcomes
● Strong communicator with the ability to build trust and influence
● You move with urgency, take ownership, and focus on results
● Willingness to travel for partner meetings, conferences, and team collaboration
● Experience in life insurance or adjacent verticals
● Background in B2B marketing, thought leadership, or demand generation within insurance
What Success Looks Like
● Revenue grows through new partnerships and expanded partner spend
● Teams are performing, accountable, and operating without constant oversight
● Partners stay, grow, and increase their investment over time
● Healthcare.com becomes a go-to partner across Medicare, ACA, and ancillary distribution
● A scalable distribution engine is in place that supports long-term growth
Founded by industry experts in 2014, Healthcare.com is a data-driven, intelligence-informed marketplace where millions of consumers have explored, shopped for and enrolled in health insurance and Medicare plans. We put care, data, and a decade of experience into helping you choose the right plan. With us you can easily shop health plans for individuals, for families, for seniors. Trusted by 10 million customers a year, Healthcare.com is the data-driven choice that matches you to the right health insurance plan. We use proprietary data and machine learning technology to match consumers with distributors, ensuring each consumer gets enrolled in the right plan for them and their families.
Healthcare.com also operates Pivot Health, an insurance marketing company and healthcare services provider that offers a variety of coverage options to consumers on behalf of top-ranked insurance carriers and healthcare organizations. We develop custom health insurance programs and coverage solutions in partnership with insurance carriers. In addition to our own solutions, we have put together a portfolio of non-proprietary health insurance and healthcare solutions that we believe meet the needs of our individual members. Our products range from short-term medical insurance, dental and vision, supplemental indemnity, and accident and illness products.
