Apptio

Great opportunity to become a huge force in the software industry. I am not aware of a single company out there with a clearer path to becoming a software giant. Stable revenue stream; the company and the jobs it provides will be around for years. Really nice people and a fun place to spend your days.

Appears to have near zero chance of actually realizing potential due to the inability to transition from a startup to a product company.

Nobody at any level has a real vision for the future. Lots of corny catchphrases and taglines like "make our customers wildly successful," but nothing that grounds how they plan to do that.

There is a severe deficit in the upper levels of the engineering team. Some of the engineering decisions and practices made by the very top of the department are shockingly amateur and outdated, resulting in a platform that is built on spaghetti code and is apparently incapable of adding trivial features and fixing minor bugs.

There is a total refusal to acknowledge this deficit by the executive team. They're all about sales and marketing and could not care less about the quality of the product, and this attitude shows big time.

The engineering quality is embarrassing, and somehow they brag about it and delude themselves into thinking it is great simply because they found a large market need and they've ridden that wave to relative success.

They better hope a company led by real engineers does not come along and challenge them, because they will lose easily.

Clean house in the engineering department. It may be painful, but your leaders there are really holding the company back. It's not 2008 anymore, and outdated technologies and patterns are outdated for very real reasons. Modern technology will make the features your customers want trivial to add, and will give you the power you need to really become an industry giant.

You can do it, but you have to have the courage to make those tough decisions and hand management of your engineering department to people who haven't been hiding in a dark closet for the past decade and actually know how to build proper, modern software.

The future of your company depends on it.