If your a woman, you’ll be told to smile more - Anonymous employee Upside Employee Review

1.0
Mar 27, 2024
Anonymous employee
Recommend
CEO approval
Business outlook

Pros

None to mention from my experience

Cons

If you’re a male in sales and talk down to women, you’ll grow fast here! Head strong women who speak out against the utterly toxic culture get told they need to smile more, are talked over in meetings, and “forgotten” when scheduling strategy meetings or important calls with customers. Gals - STAY AWAY. This is the most toxic, classically male chauvinistic culture I’ve ever seen. You can do so much better than this gaslighting puppet show

Explore other reviews about Upside

5.0
Feb 4, 2026
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

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Upside Response
4mo
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
Dec 3, 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
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Upside Response
6mo
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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