Dave Eggers The Circle IRL - Account Manager Gusto Employee Review

Smart and friendly coworkers. Excellent team culture

Tunnel visions on AI a bit too much

The product is genuinely good, too bad the same can’t be said for how they treat the people who sell it.

Leadership talks a big game about people-first culture but the reality doesn’t match. The Chicago office expansion felt like a poorly thought-out experiment, new hires were brought on without a clear long-term commitment, and layoffs came without warning, leaving people blindsided. Crossing a billion dollars in revenue and still cutting employees sends a clear message about where workers rank on the priority list. Remote work flexibility is also a glaring weakness. For a company selling HR software to modern businesses, their internal stance on where employees can work is surprisingly rigid and hypocritical. The “flexibility” messaging is mostly optics. The broader concern is the AI roadmap. The automation push feels less like an innovation strategy and more like a slow wind-down of the workforce. Employees aren’t blind to it, it creates anxiety and erodes trust. The culture of transparency they promote externally is largely a facade internally.