Pros
Some of Crayon's executive leadership team are incredibly bright, but access to them is limited to the occasional chat in the office or a training program they put together. That's where the good ends.
Cons
After spending a year working for Crayon, it is clear why they did not make Jeffrey Bussgang's rocketship list, but the competition, Klue, did. Crayon consistently misses sales targets, has high employee turnover, and fails to make decisions based on sound reasoning and data. Crayon's overall strategy is heavily based on what its competition is doing and tends to be reactive rather than proactive. This causes management to make poor, knee-jerk decisions that are not well thought out, and the downstream effects are not considered. Ultimately, the weight of these bad decisions falls on the shoulders of its mid & lower-level employees, who are forced to scramble to meet their objectives.
Crayon does not promote or hire based on merit, data, and performance; instead, their culture is to hire and promote based on cliques, vibes, and popularity, leading to an eco chamber of like-minded individuals who are there to climb the corporate ladder, not better the organization. These individuals lie, cheat, and steal their way to success, often standing on their employees' shoulders while they call themselves tall.
There is a reason the average tenure here has plummeted, and they only have two open positions. Their competition, Klue on the other hand, has 30 open positions and is growing. In a market where startups are fighting for funding, I'd be shocked to see Crayon around for much longer.