For the past year, I have not been able to figure out who Donald Trump reminded me of (besides a guy I once worked for).  And then something my wife said about Trump being a “salesperson who will say whatever the audience he is in front of wants to hear” reminded me:  he is the very embodiment of every bad trait of every bad enterprise software sales person I have met over the last 20 years.

The Interview (Campaign Phase)

• As we interviewed Trump during the campaign phase, he was willing to say just about anything he thought would get his core constituency fired up.  A bad software sales person does the same.
• Trump, we learned, used to sell for the competition (Democrats), but disavowed them and is now a True Republican.  Trump says he now believes Republicans have the best product (policies) and will sell them compellingly.  Every time I hired a salesperson from a competitor, I heard something similar.  I was never sure what to believe.  I always wondered if I was just “leasing” this salesperson until he moved on to a third competitor!
• We wanted to know what Trump’s W-2 had looked like over the prior five years.  We were assured we would be impressed (“it was yuuuge”), but the W-2 was never forthcoming.  Ditto for the bad software sales person.

The Training Phase (Transition)

• Trump, like the bad software sales person, did not seem to realize how complex the product (e.g., governing) is and how much work it will be to learn it.
• Trump, like the bad sales person, does not want to go out and meet prospects; he works from his home office a lot.
• Trump and the bad sales person do not seem willing or able to learn a lot about the product (governing) but both assure you they will be great.
• Whatever a bad software sales person learned at the last training session is his new pitch (until the next training session).  He/She can only parrot what others have told him.  Sounds like Trump and his advisors!
• When you ask Trump to present on the product (policy) he can only make vague statements, but he assures you (without any evidence) that the product is great and that you will pay for it. Like every bad sales call ever.  (See the transcript of his New York Times interview.)
• Trump is having trouble attracting the best team around him because many of the best resources do not want to work with him.  Same with a bad software sales person.  The best pre-sales engineers stick with the best sales people–they have a quota to make too!

The Sales Phase (Governing)

Trump has not started to govern yet, so we can only predict what it will be like based on the typical bad software sales person.  The bad software sales person:

• knows almost nothing about his product (government or policies) but assures prospects that it will be great/the best.
• knows almost nothing about competitive products (alternative policies) except that they are bad and his is certainly be better.
• is a good golfer who will take you to the country club if you like.
• will engage you in “locker room” talk beyond your wildest imagination.  He will even introduce you to some “hot women”.
• enjoys the finer things in life (as long as he can expense them).
• likes to bring his family along to events when it is not appropriate.
• does not seem very good at math, but is great at calculating his commissions.
• sucks up a lot of resources as the whole organization tries to make him successful.

In The End

In the case of the bad software sales person, towards the end:

• He has never made quota, but he still has a “huuuge” pipeline of opportunities that are just around the corner.
• People eventually figure out they were bamboozled.
• No one can figure out how he got hired and no one will admit to having hired him.
• He gets fired, but not as quickly as he should have been.

So far the first two phases are tracking fairly well, I hope I am wrong about the last two phases, but I am prepared for them to track as well.