Full-cycle B2B sales role selling Healthcare.coms Autopilot customer acquisition platform to telesales agencies and insurance distributors. Prospect, qualify, present, close, onboard partners, and identify upsell/cross-sell opportunities while maintaining CRM discipline and collaborating with internal product, marketing, and sales teams.
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.
Job Overview
Healthcare.com is seeking a highly-motivated Sales Executive – Marketplace Solutions to expand adoption of our Autopilot customer acquisition platform, built for health insurance & Medicare agency distributors. In particular, Autopilot serves telesales-focused health insurance agencies in ACA, Medicare Advantage, Medicare Supplement, and private under-65 health insurance lines - and delivers high-intent Healthcare.com shoppers to agencies through predictive matching, real-time decisioning, and branded, consent-driven handoffs that match consumer preferences with licensed agencies. This role is responsible for driving revenue through the sale of Healthcare.com’s customer acquisition solutions while identifying broader opportunities across our B2B distributor offerings, including Pivot Health proprietary insurance products, and other initiatives under the Healthcare.com umbrella.
This is a full-cycle sales role focused on consultative selling—not just product pitching—where success is measured both in closing new Marketplace/Autopilot business and in recognizing and coordinating cross-sell opportunities in collaboration with other Healthcare.com sales executives. The ideal candidate is a self-starter who thrives in a fast-paced, collaborative environment and has experience working with telesales agencies, health insurance distributors, or lead generation platforms.
Key Responsibilities
Full-Cycle Sales Execution
Own the sales process for Marketplace solutions: prospecting, qualification, discovery, presentations, and closing.
Manage inbound and referred leads while also driving outbound pipeline generation focused on telesales agencies and insurance distributors.
Present Autopilot(internal scoring technology) capabilities, performance metrics, and pricing mechanisms in a clear and compelling way to partner decision-makers.
Coordinate with internal teams—including Partner Solutions—for smooth onboarding of new partners post-close.
Proactively identify opportunities for upsell or cross-functional deals across Pivot Health, Insurance Distribution, and other Healthcare.com business lines, engaging appropriate internal sales counterparts.
Attend relevant industry events, virtual conferences, and telesales agency roundtables to promote Healthcare.com’s offerings, build up the prospect pipeline, and close new business.
Team Collaboration & CRM Hygiene
Maintain CRM discipline: track activity, forecast pipeline, and document partner engagements and stage progression.
Share market feedback and insights with the Product and Marketing teams to refine value propositions and improve solution-market fit.
Collaborate closely with other sales executives and subject matter experts to bring a consultative, full-stack solution approach to partner needs.
About Healthcare.com
Healthcare.com is a leading digital health platform that simplifies how people discover and purchase insurance. Our data-driven solutions span proprietary product lines (like Pivot Health), partner carrier distribution, and Autopilot—our AI-powered customer acquisition engine. By partnering with distributors, FMOs, IMOs, and telesales agencies, we help bring affordable, high-value insurance products to the millions who need them.
Qualifications Required
- 5+ years in B2B sales with proven experience selling to telesales agencies or insurance distributors.
- Demonstrated success in closing marketing or lead generation solutions (e.g., digital performance marketing, pay-per-lead programs, or customer acquisition platforms).
- Strong presentation skills, particularly in selling to agency owners, heads of telesales, or marketing leaders.
- Understanding of the telesales landscape within the individual and/or Medicare insurance markets.
- Hands-on experience with CRM systems (e.g., Salesforce, HubSpot) and digital sales enablement tools.
- Knowledge of ACA, Medicare Supplement, or Medicare Advantage and how telesales agencies operate in these markets.
- Experience in team-based selling environments where coordination across product lines and roles is key to success.
Preferred
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
Most importantly, an inclusive company culture established by an incredible team!
Get to Know Us!
https://www.healthcare.com/
linkedin.com/company/healthcare-com
Top Skills
Autopilot
CRM
Hubspot
Pivot Health
Salesforce
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