Pros
There are some genuinely cool, passionate people at HQ and in the field you'll get to work with who are enthusiastic about selling a unique product You're constantly busy so there's never a dull moment Casual dress code and office with a startup-like vibe Less hierarchical than typical companies and even execs seem willing to get involved and help out with any level employee
Cons
If I told you this company has been around for 20 years, you probably wouldn't believe me. It is at best disorganized and at worst dysfunctional. Foundational systems and procedures needed to run the business barely work or are non-existent. Even the most basic tasks are needlessly complicated because information is either wrong or you have to set up a committee to unearth it. When the same seemingly avoidable mistakes keep happening over and over people seem surprised, but nothing was done to correct them in the first place. The lack of accountability and controls lead to a never-ending trail of loose ends that will keep you up at night. Executives make grand announcements about sweeping changes with no real understanding that these projects require significant commitment and time from their limited, already overworked staff that can barely stay afloat simply keeping up with the day-to-day work. On top of that, substantial investment in resources which are needed to keep up with current priorities, let alone plans for future growth, don't happen. Goals are moving targets because even the simplest improvements are rarely achieved despite what seems like months of repetitive meetings and wasted energy. A big problem is that high turnover kills momentum. You'll keep hearing things are going to get better, but they can never figure out how. Inter-departmental communication is abysmal especially considering there are 50 people tops at HQ and everybody sits on top of each other. People aren't realistic about what we can and should focus our efforts on so you end up on wild goose chases totally out of proportion to any sort of rational risk/reward. Planning on every level is severely lacking which results in regular fire drills to even determine if a promotion can be supported properly. This leads to constantly putting pressure on our vendors--with whom we are usually months behind on payment--to try and meet our unrealistic expectations. Culture-wise, the CEO tries to instill this "sweep the floors" mentality, but it's pretty insulting considering that benefits are virtually non-existent (no 401k, overpriced insurance), pay is terrible (and uneven across titles), and there is no realistic prospect of raises or bonuses. Seriously, on the page in our HR handbook that outlines the 6 paid holidays you get off a year there is a reminder about being willing to pitch in if needed. Some occasional freebies and vague assurance that we will (likely? maybe?) hit the jackpot years down the line isn't enough to keep a workforce motivated or from flying out the door. Bottom line, the empty promises are not worth the inevitable stress and burnout. You'll either lose your mind or accept the life of working in an alternate reality.