VP - Health Plan Sales Executive

Drips • Portland, OR

4d • Remote

About The Position

Drips is a fast-growing, tech-enabled managed service transforming how health plans engage members at scale. Its member engagement solution supports health plans in improving Stars, HEDIS, HOS, medication adherence, acquisition, and retention strategies, with impacts on quality scores, member experience, revenue protection, and operating and administrative expenses.

Drips is seeking a quota-carrying VP, Health Plan Sales Executive to sell six- and seven-figure enterprise deals to payers. This is a hunter role centered on activating an existing network of senior health plan executives, developing new opportunities, guiding complex consultative sales through a disciplined enterprise process, and closing deals. The role engages C-suite and senior decision-makers across Medicare, Medicare Advantage, Medicaid, ACA, and Pharmacy lines of business. It is remote within the United States and requires 40%–50% travel, with in-person executive meetings, dinners, and lunches at least every other week.

Requirements

• A real network of C-suite and VP-level health plan executives, with direct access by phone or text, that can be activated within the first 90 days; relationships should be built over years, not just a LinkedIn list.
• 5–10+ years of successful enterprise sales experience in healthcare, preferably with health plans and digital health.
• A track record of quota achievement and consistency.
• Proven ability to close seven-figure, multi-year deals.
• A track record of converting personal relationships into meetings, pipeline, and signed contracts, with the credibility to shorten the path from first conversation to contract.
• Deep understanding of payer economics, market dynamics, complexities, and decision-making structures.
• Executive presence, strong communication, and disciplined follow-up and follow-through.
• Ability to contribute to a high-performance culture grounded in collaboration, accountability, discipline, integrity, and drive.
• Drive and hunger to learn, curiosity to ask questions, and resilience to win in a fast-moving environment.

Nice To Haves

• Enterprise sales experience with health plans and digital health.

Responsibilities

• Activate a personal network of health plan executives during the first 90 days to generate meetings and qualified opportunities.
• Own the full enterprise sales cycle for net-new payer customers, from the first executive conversation through close.
• Lead complex, multi-stakeholder sales motions focused on ROI, outcomes, and long-term strategic value.
• Use knowledge of Stars, HEDIS, CAHPS, RAF, and adherence to position solutions that deliver impactful outcomes.
• Build and maintain a healthy, high-velocity pipeline within assigned target payer accounts, anchored in existing relationships.
• Build and deepen C-suite and VP-level relationships across Quality, Operations, Finance, and Digital Strategy, including maintaining relationships when there is no active deal.
• Build, manage, and convert a seven-figure pipeline within assigned target payer accounts.
• Meet performance expectations for qualified leads, meetings, funnel coverage, qualified opportunities, and bookings quota.
• Lead strategic deal orchestration and account planning across multi-stakeholder buying committees, collaborating with the Drips Advisory Board and existing client leaders.
• Maintain high standards of CRM hygiene, account planning, and follow-through.
• Partner with marketing, product marketing, product, and client services teams to ensure alignment and execution.
• Travel 40%–50%, including being on the road at least every other week for in-person executive meetings, dinners, and lunches.

Benefits

• Unlimited PTO
• Competitive base salary plus commission
• Account managers handle retention, renewals, and day-to-day management so the sales executive can focus on winning new contracts.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed