About Upside
What is Upside?
Upside is a retail technology company on a mission "to advance the economic power of people living and working in the real world." Founded in 2016 (originally "GetUpside"), the company built "a new economic model that levels the playing field in brick and mortar commerce and empowers everyone to earn more. Retailers earn more profit without changing how they operate, and consumers enjoy increased purchasing power on the things they need." Its app gives shoppers personalized cash back on gas, groceries, and dining — "users earn 2 to 3 times more cashback than any other product." The scale is substantial: more than $1B in cash back has gone to consumers to date, and over $6B in commerce runs through the platform every year, with value flowing back to retail partners, consumers, and communities.
Where will I work?
Upside is headquartered in Washington, DC, with additional offices in Austin, Chicago, and New York. Most roles are hybrid: "This hybrid role is based in our Austin, Chicago, DC, or NYC office. In-office attendance is required on Monday, Tuesday, and Thursday." Some senior roles offer more location flexibility, with hybrid attendance only if you're near a hub. Teams span engineering, data, product, marketing, and operations across the four offices.
What is the Upside team like?
Upside's culture runs on five values: "Be an owner," "Make it measurable," "Represent the real world," "Make the impact worth the effort," and "Always share whether we succeed or fail." Engineers are "expected to gather the right context from those around them and take thoughtful, calculated risks," cultivating "a collaborative and safe environment" where people "speak up to name problems." The company champions a "transparent culture" and active Employee Resource Groups, and it backs that reputation with recognition as a Built In Best Place to Work in Washington, DC.
Work-Life Balance
Time off at Upside is generous: "Unlimited PTO + 10 paid federal holidays + our annual, week-long Winter Break," alongside a stated "flexible work environment." New parents get "generous parental leave for all new parents," supported by "family planning programs" and a partnership with Carrot Fertility "to support your family forming journey." Emotional and mental-health support programs round out the wellbeing offering.
Perks and Benefits
Benefits include "medical, dental, and vision coverage starting on Day 1," "emotional and mental health support programs," and a "401(k) program." Employees receive "equity (ISOs)" for ownership in the company, "family planning programs + paid parental leave" plus the Carrot Fertility partnership, "physical fitness and wellness memberships," a "learning and development stipend," and "lunch reimbursement for in-office employees." Upside also publishes salary ranges on its job postings.