How Many People Work at Upside? Headcount and Employee Trends

Upside is an information-technology company that builds a cash-back marketplace connecting consumers with gas stations, restaurants, and grocery stores. The organization employs about 290 people and has modestly expanded its workforce with 16 recent hires while keeping departures low at 11. This steady growth suggests a measured scaling strategy that aligns staffing levels with product and market demands.

Marketing & Product and Engineering are Upside’s two largest teams, each accounting for roughly one-quarter of total headcount at 69 and 67 employees, respectively. Sales & Support follows with 58 employees, underscoring the company’s focus on both customer acquisition and service. Business Management (31) and Operations (20) round out the core functions, while smaller groups such as IT, Finance & Administration, and Human Resources provide essential internal support. The remaining employees are distributed across Program & Project Management and other specialized roles, giving the organization a balanced functional footprint.

Upside’s headquarters presence is concentrated in Washington, DC, which hosts 64 employees. Outside the capital, talent is spread across Austin (38), New York (30), Chicago (27), and several West Coast hubs including San Francisco, Los Angeles, Seattle, and Denver. An additional 108 employees are categorized under “Other,” reflecting the company’s use of remote or distributed staff and smaller satellite locations. This geographically diverse footprint enables Upside to tap into multiple labor markets while staying close to partners in the retail and energy sectors.