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 Senior Director of Payer Partnerships to build and own a pipeline of Medicaid MCO and Medicare Advantage relationships across the government payer market. This is a senior enterprise sales role for someone who knows how to navigate complex payer buying cycles, build executive-level relationships, and move high-value partnerships from early conversation to signed contract.

This role reports to the EVP of Sales and GTM and will partner closely with Marketing, BDR, Finance, Product, and Client Success to shape payer strategy, structure deals, and ensure a strong transition from close to implementation.

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 state meetings, payer meetings, and industry conferences

What You’ll Do:

• Own a defined set of target accounts or territory within the Medicaid MCO and Medicare Advantage market

• Build, manage, and advance a qualified pipeline of high 6-figure to multi-7-figure payer partnership opportunities

• Own the full enterprise sales cycle from prospecting and discovery through proposal, negotiation, contracting, and close

• Lead outbound prospecting in partnership with BDR and Marketing, including cold outreach, referral development, conference follow-up, and targeted account-based campaigns

• Build relationships with VP and C-suite stakeholders across health plans, including clinical, operations, finance, strategy, population health, and network leaders

• Conduct discovery and executive-level conversations to understand payer priorities, pain points, budget drivers, and state-level requirements

• Deliver tailored presentations and value propositions grounded in outcomes data, SDOH needs, HEDIS performance, member engagement, quality improvement, and total cost of care

• Navigate complex buying processes, including RFPs, procurement cycles, legal review, multi-stakeholder approvals, and state or plan-specific compliance requirements

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

• Maintain strong pipeline discipline, including clear opportunity staging, next steps, deal risks, forecasting, and CRM hygiene

• Represent Upside at industry conferences, state health agency events, payer forums, and managed care association meetings

• Coordinate with Client Success and Implementation to ensure commercial commitments are clearly handed off and operationalized after close

• Support team growth, market expansion, and additional GTM initiatives as needed

What We’re Looking For:

• 5–8+ years of payer sales, enterprise healthcare sales, business development, or payer partnerships experience

• Proven track record closing complex enterprise contracts with Medicaid MCOs, Medicare Advantage plans, government payers, or adjacent health plan buyers

• Experience managing the full sales cycle independently, from outbound prospecting through negotiation and close

• Demonstrated success selling high-value healthcare solutions, ideally with high 6-figure to 7-figure deal sizes

• Strong understanding of Medicaid managed care, Medicare Advantage, government payer priorities, and health plan decision-making

• Experience selling or partnering in housing stability, SDOH, care management, care coordination, population health, behavioral health, social care, or adjacent healthcare services

• Comfort engaging senior health plan stakeholders, including VP, SVP, and C-suite buyers

• Ability to translate outcomes data, quality metrics, SDOH needs, HEDIS priorities, and total cost of care into a clear payer value proposition

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

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

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

• Strong pipeline management discipline and ability to prioritize a defined book of target accounts

• Experience partnering with BDR, Marketing, Finance, Product, and Client Success teams to develop and close opportunities

• Strong written and verbal communication skills, including executive presentations, proposal development, and RFP support

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

Compensation and Benefits:

• Base salary range: $140,000–$150,000

• On-target earnings: $280,000–$300,000

• Medical, dental, and vision coverage

• Paid time off and company holidays

Upside is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, pregnancy, or other applicable legally protected characteristic. Upside is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans. If you have a disability or special need that requires accommodation, please let us know.