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Should I pursue enterprise or "small software businesses on the Internet" (SSBOTI) first?


My background is in enterprise, so I’m far more comfortable with how things work in that sphere. My job was to design integrations for an enterprise communication generation system, and provide advice on how people could get up and running as quickly as possible. Generally, “as quickly as possible” meant “excruciatingly slowly”.

Typical enterprise problem: too much information needed to be communicated to too many people, and in the end nothing fits.

Now, normally the answer would be: agile. At least with the tool I was working with, though, that wasn’t really possibly; the backend was too tightly coupled to the frontend. You really had to get it more or less right the first time, or do it over.

That gave me the idea of a communication planning tool that gave you that flexibility to introduce more agile processes up front, and ease some of those burdens.

I’ve got a couple of conversations bubbling along nicely, but I’m painfully aware that enterprise deals routinely take a year or more to close. So, I’ve sort of chickened out and tried to set up a sideline for “small software businesses on the Internet”. This has meant introducing some additional, unplanned development, but also means I have to understand a brand new market which is (currently) quite opaque to me.

Anyone got any experience with similar challenges they could share?


Pardon my ignorance, but what is “communication planning”?

Just like you, I have a draft plan for a project that could benefit the big corps most… and just like you I suspect it will take my lifetime and then some to see the results, so I put it onto a shelf.

So if my vote count, start small.

On the other hand, in some modern corps departments are pretty independent and resemble small and mid-size businesses. You may want your solution to not require the company-wide acceptance, but only department or even group-wide. Then your chances are higher.

P.S. If you don’t mind me saying, your web-site copy needs improvement! When I skim the page and only read the headers, I get no information what it is about. Only “It’s pretty simple. Or not”. Headers alone should tell the whole story, even if barebone. The copy also doesn’t convey the value – it says “what” but doesn’t prominently say “why”. Compare to Drip.


I agree with @rfctr. I’m not an Enterprise specialist at all, but it would seem like the biggest hurdle would be getting Enterprise to buy your bootstrapped product.

The questions they’ll always ask are

  • who else is using it?
  • what do we do if the startup goes under?

Getting customer #1 is never easy, but Enterprise customer #1 seems to be extremely hard. But maybe your Enterprise connections are good enough to get you over that hurdle.


Whenever I meet someone who’s business has a large enterprise customer base, I always ask them how they made the transition. The answer is pretty much always “we hired a bunch of salespeople.”

The one exception was github. Not too long ago I found myself in a van in mexico with the head guy behind github enterprise. He told me that they don’t actually do any outbound marketing, though I bet that’ll change if it hasn’t already.

You can easily sell stuff to small teams within large companies, though. From the vendor’s point of view they don’t look a lot different from a startup or another small business.

Anyway, none of this really has anything to do with you. If you have an in with a few customers and can pre-sell your product for 5-6 figures, go for it. :slight_smile:


@rfctr, yes, the copy needs a complete overall. You’ve prompted me to rip it all out and replace it entirely. Thanks! “What’s communication planning?” Well, a typical customer I’d work with would have around ~1000 different types of communication and send out millions or 10s of millions of individual communications per year. By “communication planning” I mean working out what those 1000 communications need to say, and when they need to be sent.

@FrankHarper, I’ve got a few good connections, whether they’re good enough: time will tell. Will they buy from a small fish? In the case of one company, it’s against policy for them to even TALK to me. They are though; they’ve got a problem I can solve, and there’s not really anyone else in this exact space (to my knowledge.)

@starr, Atlassian is also supposed to have made it into enterprise without a sales force; I think they still say that but I take it with a grain of salt. Like you say, they got into teams or departments and spread. As for pre-selling: I’ve tried it, not much luck. I think I’ve read a few things recently about product being a very useful thing to have when you’re trying to sell. I figure it’s worth a try :smiley: . As for a sales team: that’s me for now. I’ll hire a team when I’m ready.

Thanks for these thoughts! It sounds like going small as a hedge is the way to go. I’ll just have to work out how to overcome the time management challenges!