Upside, the digital marketplace that delivers personalized cash-back offers on everyday purchases, employs about 290 people. Recent staffing activity shows 20 hires and 16 departures, resulting in a modest net gain in overall headcount. The balanced growth suggests the company is maintaining a steady workforce while continuing to refine its product and market reach.
Marketing and Product is the largest group at Upside with 69 employees, closely followed by Engineering at 67 and Sales and Support at 58. Business Management (31) and Operations (20) provide additional scale, while Information Technology (18), Finance and Administration (13), Human Resources (7), and Program & Project Management (3) round out internal functions. An additional 4 employees are classified in Other roles. This distribution indicates a strong emphasis on product development, customer acquisition, and ongoing operational support.
Upside’s workforce is distributed across several hubs, with the greatest concentration in Washington, DC (62 employees). Austin (38), New York (30), and Chicago (27) also represent significant talent centers. Smaller teams are based in Los Angeles, San Francisco, Baltimore, Houston, and Las Vegas, while 110 employees work remotely or from other locations. The mix of urban offices and remote roles highlights the company’s flexible approach to hiring talent where it is available.