VP of Health Plan Sales

About Upside:

Upside is a housing-focused care partner helping people experiencing housing instability take the next step toward stability. We partner with health plans and care organizations to identify members at risk, build a clear housing plan, and drive the work forward through placement and stabilization.

Upside owns the entire housing process from start to finish. Our team engages members, coordinates with local providers and community resources, manages logistics and documentation, and stays involved until the issue is resolved. Our approach is human-first and outcome-driven, measured by real results like stable housing, completed moves, safer living environments, and successful transitions.

About the Opportunity:

Upside is hiring a VP Sales, Health Plans to lead growth across Medicaid MCOs and emerging Medicare Advantage opportunities. This is a senior sales leadership role focused on building and closing large-scale partnerships with health plans that are looking for solutions around housing stability, SDOH, value-based care, member outcomes, and total cost of care.

This role reports to the EVP of Sales and GTM and will own a high-priority payer segment, including flagship account strategy, executive relationships, RFPs, pipeline development, pricing strategy, and contract execution. You’ll work closely with Marketing, BDR, Finance, Product, Clinical, and Client Success to move complex payer opportunities from first conversation through implementation handoff.

Work Location and Schedule:

• Full-time, fully remote (must be based in the United States)

• Coverage aligned to Eastern or Central time

• Monday–Friday schedule, with travel as needed for payer meetings, state meetings, RFP-related meetings, and industry conferences

What You’ll Do:

• Own and execute the sales strategy for Medicaid MCOs and emerging Medicare Advantage opportunities

• Build and manage a qualified pipeline of high-value payer opportunities, with accountability for revenue targets

• Lead flagship health plan opportunities from account mapping and outreach through proposal, negotiation, contracting, and close

• Identify and convert high-priority payer opportunities across Medicaid managed care, Medicare Advantage, and adjacent government-funded healthcare programs

• Build relationships with senior payer leaders across population health, clinical, quality, operations, finance, strategy, and executive leadership

• Serve as a credible face of Upside in senior conversations with health plan executives, state stakeholders, industry groups, and market partners

• Lead the strategy and execution of major payer RFP responses, ensuring Upside’s clinical, operational, and financial value proposition is clearly positioned

• Tailor Upside’s housing stability and SDOH value proposition to each payer’s priorities, including quality, cost of care, member engagement, compliance, and outcomes

• Partner with Finance and Product to structure pricing and deal models, including PMPM, shared savings, performance-based, or other payer-aligned arrangements

• Work with Product and Clinical teams to ensure payer feedback, compliance needs, reporting requirements, and market expectations are reflected in future roadmap discussions

• Provide competitive intelligence and market feedback to strengthen Upside’s positioning in housing, SDOH, value-based care, and payer partnerships

• Build and maintain relationships with state health agencies, managed care associations, payer forums, and industry groups

• Maintain strong CRM discipline, including pipeline updates, forecasting, next steps, deal risks, and executive-level reporting

• Coordinate cross-functionally to ensure proposals include the latest outcomes data, ROI story, operational model, and implementation assumptions

• Partner with Client Success and Implementation to ensure closed partnerships are handed off clearly and commercial commitments are operationalized well

• Support broader GTM strategy, market expansion, and team growth as Upside scales its payer partnerships function

What We’re Looking For:

• 10–15+ years of payer sales, healthcare enterprise sales, business development, or payer partnerships experience

• 7+ years of experience selling to or partnering with Medicaid MCOs, Medicare Advantage plans, health plans, or government payer organizations

• Proven track record personally closing large-scale payer contracts and managing high-value revenue targets

• Experience owning a full sales cycle independently, from account mapping and prospecting through negotiation, contracting, and close

• Deep understanding of Medicaid managed care, Medicare Advantage, payer priorities, government-funded healthcare programs, and health plan buying cycles

• Experience navigating complex RFPs, procurement processes, legal review, compliance review, executive approvals, and multi-stakeholder decision-making

• Strong understanding of SDOH, housing stability, value-based care, population health, quality improvement, member engagement, and total cost of care

• Experience selling or positioning solutions related to housing, care management, care coordination, behavioral health, social care, complex populations, or adjacent healthcare services

• Ability to engage credibly with C-suite and senior payer stakeholders, including clinical, finance, operations, quality, strategy, and population health leaders

• Familiarity with PMPM, shared savings, value-based, performance-based, or other payer contracting models

• Experience partnering with Product and Finance to shape pricing, deal structure, reporting expectations, and payer-specific contract terms

• Strong written and verbal communication skills, including executive presentations, proposals, RFP responses, and internal deal strategy materials

• Strong pipeline management and forecasting discipline, especially in long-cycle enterprise sales environments

• Existing relationships with Medicaid MCOs, Medicare Advantage plans, state health agencies, managed care associations, or payer executives preferred

• Experience with ACAP, MHPA, state Medicaid agencies, or managed care industry groups is a plus

• Bachelor’s degree preferred; MBA, MPH, MHA, or related advanced degree is a plus

• Ability to travel as needed for payer meetings, conferences, state meetings, and market development

Compensation and Benefits:

• Base salary range: $175,000–$200,000

• On-target earnings: $350,000–$400,000

• Stock options

• Medical, dental, and vision coverage

• Paid time off and company holidays