Pros
A willingness to hire people from non-conventional backgrounds makes for an energetic and social office culture. With work (and some luck) you can find opportunities to build your technical skills. Some talented and smart coworkers to learn from. A few interesting engineering and business challenges such as Pro Bono work. Room to propose new ideas in an evolving company. Politics/staffing has gotten less blatantly nepotistic over time. A newish HR representative is genuinely receptive to feedback and committed to being a fair arbiter (taking this role over from the current CEO). After a long rocky stretch, the company seems to be adapting. Newer hires are getting more guidance and room to specialize.
Cons
We were stuck in a disappointing sales rut last year. The sales team pursued any lead without a solid plan on what we had to offer, with foreseeable results. Solid helmsmanship on the emerging product side was especially lacking. Leadership underestimated the difficulty of the pivot. Bulk of analytix boils down to SQL aggregations, not far removed from vague assertions in Excel. Past work centered on tedious domains such as headcount reduction. An opinionated CEO prone to defensive outbursts and crude jokes that feel out of place in New York in 2019, though he tries to maintain friendships with employees. Miscommunication from leadership regarding benefits etc. hurt morale. (Misleading town halls were thankfully discontinued.) A troubling lack of oversight over toxic managers/teams (a small minority, to be fair) which seems to be getting addressed. Experiences could vary wildly depending on staffing. Many people who quit felt that they were stagnating due to a lack of impactful, well-defined work. A sometimes-harmful culture of insecurity/impostor syndrome, perhaps relating to a lack of experience outside of CKM. Seniors, even the most able, can be defensive, cliquish, or condescending in regard to technical questions.