Pros
Lots of individual talent and your teammates are willing to share their knowledge with you Important mission
Cons
Esper is a classic case of a company with potential that gets completely squandered by poor leadership and a lack of vision. During my time there, it was clear there was no consistent strategy, just reactionary pivots and buzzword-heavy direction changes. The organizational structure was fragmented, with limited cross-functional alignment. Leadership operated in silos, and important decisions were sometimes delayed or made without input from the teams doing the work on the ground. Turnover was a constant theme. New employees joined regularly while others departed without explanation, contributing to a sense of instability. Morale suffered as a result, especially when departures felt sudden or unclear. There were also multiple changes at the executive level during my tenure, each bringing a new vision that rarely aligned with the previous one. This made it difficult for teams to build lasting momentum or trust in the direction of the company. If you’re looking for stability, mentorship, or transparent leadership, this ain’t the place. Until Esper figures out what it wants to be and gets leaders who can steer it there, I recommend you approach with caution.
