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      Upside

      Engaged employer

      Upside reviews

      terrible experience - Marketing Upside Employee Review

      1.0
      15 Aug 2024
      Marketing
      Recommend
      CEO approval
      Business outlook

      Pros

      - Many of the mid-level leaders are great, assuming they don't get kicked out as part of yet another layoff

      Cons

      - Narcissistic leadership that inspires zero confidence as they pivot strategies every quarter, tenure of the c-suite (other than founders) averages less than a year - Regular stealth layoffs that aren't communicated well or at all - Toxic, no fun zone culture that has everyone overloaded and working in fear - It's a startup that tries to operate like a 2,000 employee business but without any of the structure or know-how. Ridiculous red tape and meeting after meeting after meeting with no decisions being made. - A mission to "help small brick and mortar retailers compete" when in reality they kick those retailers off the platform so that they can sell to the big guys

      avatar
      Upside Response
      1y
      We’re sorry to hear that your experience at Upside was not what you had hoped for. While we know that change and growth can be challenging, we’re committed to improving communication, fostering a supportive culture, and ensuring our strategy is clear and effective. We appreciate your recognition of our mid-level leaders and the hard work of our team. Our mission remains to advance the economic power of folks in the real world, and we continue to refine how we do that. We take feedback seriously and will reflect on your concerns as we work to improve. Wishing you the best in your next opportunity.

      Explore other reviews about Upside

      5.0
      4 Feb 2026
      Senior marketplace operations manager
      Recommend
      CEO approval
      Business outlook

      Pros

      - Work life balancing - Really interesting product - Really intelligent ICs

      Cons

      - Leadership tends to make big strategy pivots every other quarter

      avatar
      Upside Response
      3mo
      Thank you for the thoughtful review and for being part of Upside for the past several years! We’re glad to hear you’re enjoying the team, the product, and the work-life balance. We appreciate the feedback on strategy shifts as well; as we continue to grow, we’re focused on continuing to drive clarity and alignment.
      3.0
      3 Dec 2025
      Anonymous employee
      Recommend
      CEO approval
      Business outlook

      Pros

      - Upside is great at making you feel like you are making a difference in people's lives, truly saving users money and improving their lives in small to large ways. -I believed in the CEO and thought his choices were sound and almost always reasonable, appreciating his honesty and transparency. -They are big on in-person bonding and host many offsites in DC which I always enjoyed and felt like they did help bring everyone together. -My personal team was incredible and is why I stayed at the company as long as I did. -The company does seem to listen to employees via surveys, etc, and make improvements to benefits. -You get a lunch stipend if you work hybrid but not if you're FT remote.

      Cons

      -Management/leadership turnover was very high and exhausting. As someone who was trying to advance their career, having a new manager every 6 months to a year made it almost impossible. -Goals change often, which is pretty standard for a non-profitable startup at this size, but it can be frustrating when you pour your heart into something and then have that work basically thrown away. -They often will hire a new VP, a silver bullet who is going to solve all their problems, just for this VP to leave or be fired XX months later. -Lots of layoffs. They are trying to become profitable and will do almost anything to get there, including laying off team members who helped them get to where they are today.

      3
      avatar
      Upside Response
      5mo
      Thank you for your feedback and for taking the time to reflect on your experience at Upside. We’re grateful for the years you spent growing with us, and it’s great to hear that you felt connected to our mission, valued our leadership's transparency, and built strong relationships within your team and through our in-person culture. Like many companies at our stage, Upside evolves quickly as we scale responsibly and build a sustainable business – a process that brings both opportunity and challenge. We continue to actively apply employee feedback to strengthen leadership and clarity as we move forward, and we’re thankful for the role you played in helping us get here.
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