There are so many that its even difficult to know where to begin. So let me just list them in a random order.
* At the top-most level, the company has good funding but doesn't know how to scale. A service-heavy organization which also spends unnecessary amounts on travel of innumerable people without adding value to those visits, seem not only pointless but also less of a "product" company.
* Biggest problem is the employee onboarding. There is no direction, no way that you get onboarded well and there is a complete absence of process.
* There is also a major issue in conveying the right message while hiring. What is explained as a strategic role during hiring process, ends up being a tactical role which is where the interest level wanes for senior people.
* The product also seems to be stuck and there is nothing new on the horizon.
* I have observed some people who work really, really hard and are constantly under pressure, while some of them have just enough work for 3-4 full days a month, something wrong with capacity planning.
* The biggest, biggest problem is the concept of power centers. There are so many discussions and counter-discussions of who all are the power centers and who should one align to. This is completely avoidable, but being in Gainsight and after observing all decisions and perspectives, you have no other way to grow than get into the politics of it all.
* There are some very good technologists, no doubt, the problem is that everyone wants to innovate technologically with something entirely new. Only hitch, this is supposed to be primarily a customer success company leveraged by technology. Here, product takes the backseat and "cool" technology quotient becomes the talk. The flipside of this is that features are completely non-consistent and you cannot do basic stuff for pretty rudimentary data models.
* Too many cooks spoil the broth? Wait till you have too many architects on one product. The discussions are a nightmare and you end up trying to convince this army of architects and end up taking a middle-ground which sets you up for failure.
* Some of the people (including quite a number of old-timers) need basic education in professional etiquette and language. The rudeness, attitude towards female employees, general temperament are highly jarring and misogynist. Also some emails which you see in the internal "fun" DL called loonies are downright racist, sexist, ageist, classist, and politically inflammable.
* The absence of a good competitor is also worrisome in a way since it fails to validate this vertical which Gainsight has carved out for itself
