Startups and Big Company Exec Before Product-Market Fit = Death

It seems like startup founders keep having to learn this lesson over and over.

Big company people have "connections" and big company process, which can be great with just the right situation, and just the right personality type. However, finding this combination is seriously rare.

Here are just a few reasons that it's not a match made in heaven 👼 :

* Is the big company person ready to work mostly on commission and sell as if their life depended on it? Usually not. Founders have more leverage than they think -- the big company exec is talking with you because they don't have better options, not because they have some kind of leverage.

The level of urgency from the "big exec" is usually not there because in a bigger company, there's always another deal in the pipeline. In a small company, you actually need to sign many of those bad deals to learn what you should be doing.

* The "connections" of the big company person could be just as good as an advisory Board member rather than your CRO. Because that is about how much they are committed to the outcome (i.e. not much).

* Your investors probably think you need the credibility, and are often pushing you to "level up" before the business is ready for it.

Problem is, most investors place zero value on company culture. In fact, many investors view your startup culture as a negative, when in fact, especially before product-market fit, it is literally your only super-power.

There is really one situation where your big company person can help a startup:

* You have more business than you know what to do with.

That's it, that's the list. If you have more business and growth than you know what to do with, you need another level of executive in your startup.

Does this describe any SaaS company you know of right now? I could probably count the companies on one hand this applies to right now.

100 times a day and twice on Sunday, I would pick the mid-level person who is smart, scrappy, and ascending over the "big company exec" coming into a role. Especially in a revenue-based role.

If you're a startup, remember that your job is to hire pirates (a little crazy, but hustle) and romantics (true believers who will survive the occasional down period). [credit Jason M. Lemkin] If your key employees are not either, then consider if they are the right fit for where you are going.

I've made this mistake personally. Let my life be a warning.