VP - Health Plan Sales Executive

Location: Remote | United States

Reports To: SVP of Sales

Type: Full Time | High Drive | High Impact| Quota-Carrying

About Drips:

Drips is a fast-growing, tech enabled managed service transforming how health plans engage their members at scale. Our member engagement solution drives measurable outcomes across the member journey, helping national, regional, and local health plans improve Stars, HEDIS, HOS, Medication Adherence, acquisition, and retention strategies.

Our work in direct collaboration with our healthcare customers directly impacts quality scores, member experience, revenue protection, and operational and administrative expenses, making Drips an indispensable partner in today’s value-driven landscape.

Job Overview:

We are seeking a top-performing, VP, Healthplan Sales Executive with experience selling six-and seven-figure enterprise deals into the payer space and, just as important, a network of senior health plan executives who will take your call. You are curious, operationally sharp, and commercially driven. You thrive in complex, consultative sales cycles and know how to navigate matrixed organizations to engage C-Suite and Senior Decision Makers across various lines of business: Medicare, Medicare Advantage, Medicaid, ACA, and Pharmacy.

This is a hunter role, and the best opportunity in your territory will be your network. You’ll be responsible for turning your executive relationships into net new opportunities, guiding them through a disciplined enterprise sales process, and closing deals that drive and deliver value for our customers. This is a unique opportunity to join a company solving some of healthcare’s most urgent challenges, with a product that delivers, a market that’s ready, and the backing of a leadership team that knows what it takes to deliver and win as a team.

What You’ll be Responsible For:

• Activate your personal network of health plan executives in your first 90 days, turning long-standing relationships into meetings, dinners, and qualified opportunities.
• Own full enterprise sales cycle ownership from first executive conversation to close for net-new payers.Lead complex, multi-stakeholder sales motions focused on ROI, outcomes, and long-term strategic value.
• Leverage your understanding and expertise 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 your existing relationships.
• Bring and deepen relationships with C-Suite and VP-Level buyers across functional lines: Quality, Operations, Finance, Digital Strategy. Stay in touch even when there is no active deal.
• Building, managing, and converting a 7-figure pipeline within assigned target payer accounts.
• Consistently hit performance expectations; Qualified Leads > Meetings > Funnel Coverage ratio (Qualified Opportunities in pipe > Bookings quota.
• Leading strategic deal orchestration and account planning across multi-stakeholder buying committees while collaborating with Drips Advisory Board and existing client leaders.
• Maintain high standards of CRM hygiene, account planning, and follow through.
• Partnering cross-functionally with marketing, product marketing, product, and client services teams to ensure alignment and execution.
• 40% - 50% Travel; on the road at least every other week for in-person executive meetings, dinners, and lunches.

What You Bring:

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

Why Join Us?:

• Territory aligned to your network, so your relationships are your head start.
• Category-defining company solving meaningful problems at scale
• Partner with leading health plans on initiatives that matter
• Enterprise sales with purpose
• A support team that allows you to focus, with account managers handling retention, renewals, and day-to-day management so you can keep winning new contracts.
• High performance culture and value-driven teams
• Competitive base + commission
• Unlimited PTO