Struggling to right itself, so ask the right questions going in
Pros
1. Paid very fairly at the start. 2. Engineering/development team here is top-notch and better than most tech companies. 3. Founding execs finally brought in new leadership to replace themselves. 4. Have been known to willingly seek outside talent in key areas. 5. If you are politically savvy (and don't mind politicking as a core part of your work), you can progress your career here. 6. Talk the right talk regarding HR capabilities and opportunities; you do feel they care.
Cons
1. Small company trying to grow up, so they trust who they know to attempt to learn completely new roles rather than listening to outside expertise they've hired (hired presumably for that expertise). 2. Sometimes take action without consultation or thinking things through: e.g. changed multiple components of pay structure in parallel and decimated the talent pool. 3. Really need skilled and experienced product management talent (to match with their top-notch eng/dev team) and somehow don't want to acknowledge this; the approach of having eng/dev responsible for all product decisions (like when you were a startup) is unreasonable and not working. 4. Have to be on the "inside" to get any pay raise after joining; they will definitely screw you out of subjective bonus payments. 5. Struggled for years to break $1B in revenue but don't really have the leadership (yet) who know how to do so.