Upside Leadership & Management

Updated on September 28, 2026

Upside Employee Reviews

What I like the most about working for Upside is the amazing people I get to team up with. Everyone here is willing to jump in, help and put in the work to make sure we deliver a great product to our Merchants and our Consumers. I have been given tons of possibilities to develop professionally, and my managers truly believe in me and support me.

Employee Image
Nika, Manager of Revenue Operations
Nika, Manager of Revenue Operations

What People Are Saying About Upside

  • Strategic Vision & Planning: Leadership communications consistently frame a clear mission to build a new model for brick-and-mortar commerce that benefits both retailers and consumers. CEO messaging links this direction to concrete category expansion and deliberate long-term tradeoffs.
  • Open & Transparent Communication: Senior leaders are described as regularly sharing vision and goals through practices like CEO AMAs and open resources. Employee accounts recall detailed explanations of the business model and mission during hiring and internally, reinforcing accessible communication.
  • Purposeful Goal Setting: Operating practices reportedly include an OKR-driven model that helps make priorities visible. Feedback suggests leadership ties objectives to company-wide forums to keep teams aligned.

Upside's Benefits

Hosts in-person all-hands meetings

Hosts in-person revenue kickoff meetings

Implements team-based strategic planning

Open office floor plan to encourage communication and collaboration

Uses an OKR operational model to clearly define goals and priorities

Utilizes an open door policy that encourages accessibility