Asana

Great emphasis on values, people, and psychological safety.

Skilled people at the company, in general.

Good product with scale capabilities, though I'm not very sure how it compares to the competition.

Lack of sense of urgency, especially with so much competition. Execution velocity and decision-making could be better.

Lack of visibility into and acknowledgement of factors contributing to a drastic slowdown in growth (beyond the economy).

I think some of this comes from a lack of appropriate leadership. There seems to be a bias towards giving responsibilities to leaders that have been at Asana for a while versus bringing in external leaders/perspectives that could bring in scale and growth experience.

Trade-off between culture (focus on nitty-gritty) and execution could be better.

I believe that Asana could benefit, in a few places, from leaders that bring in practical experience of scale and growth. Existing ones could help them more than leading without much experience outside Asana.