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The Lure of Enterprise


The money. So much money. Just a few clients and you’ll be rolling in the dough. That is the lure of enterprise. It is also, quite frequently, a trick. A game of smoke and mirrors. A rigged carnival game that will find you with turned-out pockets and a head hung low.

I came from an enterprise SaaS background when I started Graphite. I managed higher education accounts for an online college portfolio software company. I worked with admissions departments, handled RFPs (requests for proposal), rode out the 6-12 month sales cycles that some of the deals required. I also handle customer support, customer experience, and was the frontline on feature requests and bugs. Eventually, I transitioned into engineering with this company to round out my enterprise SaaS experience.

So, when I started Graphite, I was an expert in enterprise. I’d seen the deals that could be landed when working with organizations over individuals. It was only natural, in my mind, that Graphite be an enterprise software tool. This was the biggest mistake I’d ever made with Graphite and it’s what ended up hurting the company more than anything else.

To enter into the enterprise market, you generally need to have a Rolodex. Kids, a Rolodex is a—come on, I’m not old enough to have used one of these. Anyways, the enterprise market tends to need salespeople with pre-existing contacts they can tap into. I didn’t have that. But that’s only one half of the problem. The other half is closing the deal.

I surprised even myself by getting in front of some large, well-known organizations. But getting a few meetings is a far cry from closing an enterprise deal. You have to convince many people along the way that your product checks all of their boxes, is priced right, and will be around long enough to make their IT staff happy. Then, there are the legal and compliance departments.

For a small operation or a solo founder, landing all of the things you need to land to close an enterprise deal is damn near impossible. But I spent so much of my time and resources on chasing enterprise. In fact, I spent so much time on this that I let a completely viable market pass me by.

I had users, many of which would have surely paid for the product I was offering. But I all but ignored them because of my tunnel vision focus on enterprise.

The lure of enterprise is strong, but make sure you are well-informed and seriously prepared before you decide to dive head into that market. The consumer and “prosumer” markets are totally viable and may be the right path for you.