Some interesting parallels between selling enterprise software and playing poker. Part 1.

1. Texas Hold’em and Enterprise Software Sales –
Part 1
Disclaimer
I’ve been living in the Silicon Valley and working in sales, business development, marketing,
and consulting related to enterprise software for the past 23 years. I’ve been playing No
Limit Hold’em for the past 14 years, mainly with friends but occasionally in Vegas. I am by
NO means a pro poker player, and do not pretend to be a master of this great, complex
game.
Furthermore, I will not attempt to sell you anything in this blog post. I wrote it purely for fun,
and in hope of starting a conversation with folks like me, who sell software for a living and
love to play Hold’em. Through this conversation I hope to become a better sales guy... or at
least a better Hold’em player!
OK. With this out of the way here let's dive into some of the parallels I've noticed between
selling enterprise software and Hold'em poker:
 Players = Customers?
o Playing the Thursday night poker with your buddies is a lot like selling to your
existing customers. You know them, they know you. Playing in Vegas is a lot like
selling to a new customer – you are constantly trying to collect more info and learn
your prospect. All this while he is doing the same.
o One thing about playing in Vegas – you should always watch out for the local guy
at your table. Typically an older gentleman, tight aggressive player, sits on a
cushion, the dealer and the cocktail lady know him by name. If possible avoid
playing against him. What’s the parallel in software sales? Not sure. Ideas
anyone?
 Good poker players know when to push (the other players). Great players know when
to fold.
o There is no shame in folding a hand. Many times it is in fact the smart thing to do.
Likewise in enterprise sales you need to know when to “lose fast”. IOW if you smell
there is no [good] deal to make here you better get out fast cut your losses. Easier
said than done. Took me a while to internalize this principal.
o Perhaps another way to think about this is the difference between cash game and
a tournament. In a tournament the number of chips is finite. Lose a big hand and
you are the short stack at the table. Chase the wrong opportunities in your sales
pipeline and pretty soon you’ll be out of a job.
 Play the player, not your hand. Well… bluffing is certainly legitimate and expected in
poker. Not so in enterprise sales. Sure you can sell a vision, especially if you work for a
startup. If you say you never done it you’re probably a liar, or a lousy sales person. But
you don’t want to lie to your customer. Sooner or later he’ll call your bluff and will not
play with you again.

2.  Slow playing is dangerous, but can be more profitable.
o Usually holds true in both poker and sales. On one hand if you sold your customer
fast and did not maximize the initial deal size theoretically you can make it up with
repeat sales. OTOH many will tell you that if you have a strong hand better slow
play it, maximize its value NOW b/c you never know what the future will bring.
Might be a while till you get a strong hand again, your customer may go out of
business, your champion decides to quit his job, s…t happens. I’m still trying to
figure this one out. In both games. Any tips are welcome.
 The Hero or Zero Phenomenon
o Painfully true in sales. Great sales people know how to sell like winners even in
slow quarters. Great poker players know how to maximize a good run and not be
“on tilt” after losing a few hands in a row. If you can’t take a bad beat, don’t play
poker. Again, easier said than done.
There’s a lot more... When would you go ALL IN in Hold’em? And in software sales?
How to eliminate the competition and stay head to head with one player (your customer)?
Is there a parallel to “pot odds” in software sales?
And what about open source software, is there a parallel to OSS in poker?
My head is spinning. I can see this turning into a series of posts… But first I’d like to hear
your take. So c’mon, raise me!