Pros
I've spent over a decade in the device management space, and what drew me to Esper was the rare combination of technical excellence and genuine commitment to organizational health. This is a leadership team that doesn't just talk about culture—they invest in it. The company is on remarkably solid financial footing. We've been recognized repeatedly as one of the fastest-growing startups in the industry, backed by investors who truly understand the space and are in it for the long haul. That stability lets us make smart, strategic decisions rather than desperate ones. The CEO is genuinely open to feedback and committed to building something sustainable—not just chasing growth at all costs. Strategic clarity here is refreshing; everyone knows what matters. If you're energized by transformation and want to be part of a company evolving from startup scrappiness to enterprise maturity, this is an exciting place to be.
Cons
We're in a real transition—moving upmarket to enterprise while still serving a long tail of smaller customers. That means competing priorities and some growing pains as we figure out how to operationalize at scale. Not every system is fully built yet; some weeks feel like we're building the plane while flying it. The pace can be intense, and like most companies our size, you'll wear multiple hats.
