Mid-Market Account Executive, Employer 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.

Our Values:

At Upside, our values shape how we work, how we make decisions, and how we show up for our members, partners, and each other.

• Compassion: Lead with empathy, meet people where they are, and approach our work with care.

• Ambition: Think bigger than today, move with urgency, and challenge ourselves to solve hard problems.

• Respect: Communicate openly, act with integrity, and assume positive intent.

• Excellence: Good enough isn’t good enough. Take ownership and deliver outcomes that exceed expectations.

About the Opportunity:

Upside is looking for a Mid-Market Account Executive to drive new business across self-insured employers, selling our housing stability solution as a differentiated employee benefit. You’ll own the full sales cycle from identifying and prospecting target accounts through building the business case, navigating key stakeholders, and closing new partnerships.

This is a highly driven, execution-focused sales role for someone who is energized by building pipelines and winning new business. You’ll help employers understand how housing instability impacts retention, productivity, and workforce stability while positioning Upside as a point solution that fills a gap within the broader employee benefits ecosystem.

Work Location and Schedule:

• Full-time

• Remote within the U.S.

• Travel as needed for employer meetings, broker and consultant relationships, industry events, and Upside’s Boca Raton headquarters

What You’ll Do:

• Build and manage a pipeline of self-insured, mid-market employers across Upside’s target industries

• Own the full sales cycle from outbound prospecting and initial discovery through negotiation and signed contract

• Develop relationships with HR, Total Rewards, Benefits, Finance, and other employer decision-makers

• Build a compelling business case around employee retention, productivity, workforce stability, and the impact of housing insecurity

• Develop and leverage relationships with benefits brokers and consultants to generate opportunities and expand Upside’s employer reach

• Navigate complex, multi-stakeholder buying processes and tailor the sales approach based on the audience

• Partner with Sales Leadership, Marketing, and other internal stakeholders on proposals, RFPs, and go-to-market strategy

• Maintain disciplined pipeline management, forecasting, and CRM documentation

• Represent Upside at employer meetings, broker events, conferences, and other industry engagements

What We’re Looking For:

• 4+ years of successful full-cycle B2B sales experience, ideally selling into employers

• Demonstrated experience building pipeline and closing mid-market or enterprise business

• Experience selling employee benefits, healthcare, HR technology, workforce solutions, or another employer-focused point solution strongly preferred

• Proven ability to prospect into and influence senior HR, Total Rewards, Benefits, and Finance stakeholders

• Tenacious and highly motivated approach to new business development, with the ability to create momentum in a developing market

• Strong consultative selling skills and ability to translate a solution into a clear business and financial case

• Comfort selling a newer category or point solution where buyers may need education on why the offering belongs in their existing benefits ecosystem

• Strong pipeline discipline, follow-through, and forecasting skills

• Experience working with benefits brokers or consultants preferred, but not required

• Willingness to travel for employer meetings, partner meetings, and industry events

Compensation and Benefits:

• Base salary: $120,000–$140,000

• On-Target Earnings (OTE): $500,000

• Uncapped variable compensation tied to new business closed

• 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.