Mid-Market Account Executive, Sales

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.

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…