My biggest challenge was the constant organizational change. During my approximately 1.5 years at the company, I had six different managers. With leadership changing so frequently, it became incredibly difficult to build momentum or execute on long-term initiatives.
Priorities shifted constantly, roles evolved without much clarity, and success often felt difficult to define because expectations changed so often. Customer segmentation also lacked consistency, making it unclear who owned what and what success should actually look like. As a result, teams were frequently reacting to change instead of executing against a stable strategy.
The partnership between Customer Success and Sales could also feel unnecessarily adversarial at times. Instead of operating as a unified team with shared goals, there were moments where priorities felt misaligned, creating friction that ultimately impacted both employees and customers.
There was also a lack of consistent guidance, coaching, and strategic direction, which made it challenging to feel supported or confident that you were focusing on the right work. Turnover was noticeably high, which only added to the instability. While change is expected at startups, the pace and frequency made it difficult to establish ownership or see projects through to completion. Career growth also felt limited, as there wasn’t much consistency in leadership or clear investment in employee development.
Overall, I learned a tremendous amount about AI, but the experience was ultimately more draining than rewarding due to the lack of stability, constantly shifting direction, and inconsistent leadership
