Pros
Cloudinary has a genuinely people-first culture. The work environment is relaxed, respectful, and supportive, with a strong emphasis on work-life balance. In many ways, the company truly tries to treat employees like humans, not just resources. The people are generally very good - smart, kind, and collaborative. I also had positive experiences with direct managers, who were usually caring, available, and personally supportive.
Cons
The main issue is that the company has felt stagnant for a long time. There is a strong tendency to play it safe, avoid risk, and protect the existing business rather than make bold decisions that could create real growth. This seems deeply connected to the founders’ conviction and the company’s overall defensive mindset. The people-first culture, while valuable, can sometimes go too far. In practice, it can slow execution and create a lot of management overhead around interpersonal issues, alignment, and internal sensitivities. At times it feels like borderline toxic positivity - problems are acknowledged softly, but not always dealt with decisively. A lot of people stay because they are treated well, have flexibility, and can work from home when needed. But there is also a sense that many know the company is not really going anywhere, and are mainly waiting for liquidity or a secondary opportunity.