Pros
Writer is a good place if you want to get hands-on experience in AI. The pace is extremely fast, and you will learn more about enterprise AI adoption, customer use cases, and the challenges companies are facing with AI transformation than you would at most companies. For someone looking to quickly build AI expertise, it is a strong environment to accelerate that learning.
Cons
The biggest challenge is the constant organizational change, especially within Customer Success. The reorganization from traditional Customer Success Managers into separate AI Adoption Lead and Transformation Lead roles created more confusion than clarity. While the intent may have been to specialize responsibilities, in practice it often confused customers and created unnecessary complexity internally. The split has made ownership unclear, and many employees are stretched thin because of retention challenges and ongoing turnover. Instead of making teams more effective, it feels like everyone has become overwhelmed trying to cover gaps. A simpler model of returning to a more traditional CSM structure — where teams can divide and conquer accounts with clear ownership — would likely create more focus, better customer relationships, and more manageable portfolios. There also appears to be an imbalance between the Transformation Lead and Adoption Lead roles, with the Transformation side often receiving more visibility and priority despite both roles being critical to customer outcomes. The broader concern is the cycle of frequent reorgs and instability. Major changes seem to happen repeatedly without enough validation of how they will impact employees or customers. The company moves quickly, which can be valuable, but large structural decisions need more thought and employee feedback before being rolled out. Customer Success is also becoming increasingly difficult because the AI market is getting more competitive. Many customers are still experimenting with AI tools rather than deeply adopting one platform, which makes driving adoption and proving long-term value much harder. The company positions itself alongside frontier AI companies, but compensation and equity do not always reflect that comparison.