VP Strategic Partner Sales

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.

Healthcare.com is seeking a strategic and commercially-minded VP, Strategic Partner Sales to structure, negotiate, and close complex, high-impact distribution and partnership deals. This role will focus on high-impact, customized agreements that go beyond Healthcare.com's standard partner offerings—often involving mutual commitments, multi-product integrations (e.g., Pivot Health + Autopilot), or tailored enterprise solutions that address unique partner needs. The VP will also support other team members, including the CRO and CEO, in closing enterprise deals with strategic accounts.You will be responsible for driving deals from early-stage qualification through signed contract, including receiving hand-offs from other sales team members or executives and leading the assessment, presentation, and completion of these opportunities.

This includes coordinating across internal stakeholders and directly influencing the company’s most strategic Revenue partnership opportunities.This role is ideal for a candidate with experience in B2B sales and business development, particularly in healthcare or insurance, who thrives in deal design, cross-functional negotiation, and long-cycle enterprise selling. You will work directly with Healthcare.com’s executive team and play a critical role in shaping the company’s partner ecosystem and growth trajectory.

Healthcare.com is a digital health insurance marketplace and distribution platform committed to expanding access to affordable healthcare coverage. Through our proprietary product line under the Pivot Health brand and our tech-enabled acquisition platform Autopilot, we connect millions of consumers to the right health insurance products. Our solutions span short-term medical, supplemental, and emerging insurance products, with a growing network of carrier and distributor partnerships.

Support deal structuring, pricing strategy, and negotiation for complex distributor and enterprise partnerships, in close collaboration with an executive who will lead these efforts.Develop and close opportunities that bundle multiple solutions (e.g., Insurance Product Distribution + Autopilot) or require custom contracting.Support the go/no-go decision on strategic sales decisionsOwn the sales process from qualified lead to signed agreement, coordinating across executive sponsors and internal teams.Maintain deep pipeline visibility and manage high-touch engagement with strategic partners throughout the sales cycle.Support internal pipeline reporting and opportunity sizing for Strategic Partnerships.

Partner with executives to assess and track deal progress.Support the CRO and CEO on top-priority strategic accounts and initiatives.Represent Healthcare.com for strategic partner sales at partner on-sites, industry meetings, and trade shows, supporting executives in advancing and finalizing strategic account opportunities as needed.

Partner closely with Executive, Legal, Finance, and Product to shape mutually beneficial terms and scalable deal structures.Collaborate with Partner Solutions, Ops, and GTM teams to ensure operational alignment pre-signature and enable smooth post-sale transitions.Build internal confidence through rigorous documentation, opportunity sizing, and strategic rationale.

5+ years of B2B sales, strategic partnerships, or business development experience, preferably in digital health, insurance, or related regulated industriesProven success in designing and closing complex, high-value distribution or technology partnershipsStrong project management skills, with demonstrated ability to coordinate complex initiatives, maintain clear organization, and manage multiple stakeholders effectivelyStrong experience working across legal, product, and finance to structure scalable, executable dealsExceptional executive presence and communication skills; able to engage C-level stakeholders internally and externallyDeep familiarity with the insurance ecosystem—including FMOs, IMOs, digital brokers, carriers, and platforms—is highly preferredTrack record of managing enterprise sales cycles, with ability to demonstrate results and deal velocity

Experience bundling multiple products/solutions into strategic agreementsFamiliarity with digital insurance distribution platforms and performance-based acquisition modelsExpertise in sales enablement, contract lifecycle management tools, and CRM systems (e.g., Salesforce, HubSpot)Strong financial acumen and comfort with deal modeling and contract incentives or financial commitmentsBenefitsOpportunity to work from homeExcellent work environmentMedical, dental, and vision insuranceUp to 15 days of paid time off11 company observed holidays8 weeks of paid parental leave401k plan with company matchLife insuranceProfessional growth opportunityMost importantly, an inclusive company culture established by an incredible team!Get to Know Us!https://www.healthcare.com/linkedin.com/company/healthcare-comApply for this job