Remote Health Plan Enterprise Sales Executive

Drips; Portland (OR); Remote; USD 200,000 - 300,000; Full time

Benefits offered by this job

Unlimited PTO

Competitive base + commission

Job summary

Drips is seeking a VP, Healthplan Sales Executive to leverage a network of C-Suite health plan leaders and close multi-year, seven-figure enterprise deals in the payer space. You will navigate complex, matrixed organizations and drive strategic sales motion across Medicare, Medicaid, ACA, and Pharmacy.

You will own end-to-end sales cycles, build executive relationships, and guide opportunities through to closure while collaborating with cross-functional teams.

Qualifications

• Network of health plan executives you can activate within 90 days.
• 5–10+ years of enterprise sales experience in healthcare, preferably with health plans.
• Record of closing seven-figure, multi-year deals.
• Proven ability to turn relationships into meetings, pipeline, and signed contracts.
• Deep understanding of payer economics and market dynamics.

Responsibilities

• Activate your health plan executive network in 90 days to generate meetings and opportunities.
• Own full enterprise sales cycle from first conversation to close for net-new payers.
• Lead multi-stakeholder sales motions focused on ROI and long-term value.
• Maintain a high-velocity pipeline within assigned payer accounts.
• Collaborate with marketing, product, and client services to ensure alignment and execution.
• Travel 40–50% for in-person executive meetings and dinners.

Skills

Executive network

Enterprise sales

C‑Suite engagement

Healthcare payer sales

Negotiation

Job description

Drips is seeking a VP, Healthplan Sales Executive to leverage a network of C-Suite health plan leaders and close multi-year, seven-figure enterprise deals in the payer space. You will navigate complex, matrixed organizations and drive strategic sales motion across Medicare, Medicaid, ACA, and Pharmacy.

You will own end-to-end sales cycles, build executive relationships, and guide opportunities through to closure while collaborating with cross-functional teams.