Pros
Some really smart, kind, and empathetic people across all teams. Flexible working environment.
Cons
Leadership has done a great job of hiring talented people. The problem is that the founders struggle with letting go and allowing the people they hired do what they do best. They’ve done two rounds of layoffs in 2023 and the business is still struggling to grow, so I wouldn’t be surprised if there is another round of layoffs coming. The founders made all the decisions about who would be laid off in the last round, rather than consulting individual’s direct managers or other leadership. They eliminated entire teams including the Infosec team (shocking considering they hold so much customer financial information. The founders are very smart people, no one can deny that. Yes, they’ve had success selling their previous two startups, but those companies were tiny and not anywhere near the scale of Pilot. If Pilot has any chance of succeeding, they need to let go and trust the individuals that they hire, especially those in leadership positions. These people come with years, some with decades of experience in their particular function, and know what they are doing. The founders come from software engineering backgrounds, not sales, marketing, information security, product management, design, finance, HR, IT, recruiting, or facilities.