At-a-glance, this wasn’t a promising opportunity. My competition was the established incumbent in my target account and carried “trusted adviser” status in a key circle of internal influence. Moreover, I was a little late to arrive in this competitive scenario so I didn’t even forecast this engagement in an “Opportunity” stage because it would be a long-shot for me to close. However, for my competition (the CEO of an emerging technology company) this was supposed to be an easy, simple, “renewal & upgrade” deal coupled with an opportunity for a co-marketing agreement, right? Think again.

Most CEO’s may have successfully driven an end-to-end sales process at some phase in their company’s growth and development. But more often than not, as the company’s products matured and evolved, many settle into their primary role as the chief visionary and executive responsible for achieving investor requirements.

The result: CEO sales skills get rusty or they may not even be aware of  the recent subtleties and nuances of engagement that have evolved and are preferred by today’s decision-makers. The fact is, keeping up with changes in the technology sales industry aren’t a priority for a company’s senior executive and in general, it’s not easy to do. However, just as world-class professional athletes have training camps, ongoing practices and drills, coupled with personal performance coaching to stay competitive… so do the top technology sales reps. Therefore, matching-up a highly motivated and well-intentioned CEO against a well-trained, tuned-up sales executive may not be a fair fight. The bell had been rung, and I salivated like Pavlov’s Dog… sensing that a high-profile slam dunk on a competitor was now possible. Here’s why:

  • A full-time CEO is a part-time sales rep.  Focus, or lose to those who do.
  • No Escalation Option. Things happen. Something will go wrong.  Guess who has just put their executive reputation on the line?
  • Limited Leverage in Negotiations. Have you ever seen a senior executive being humbled and having to put their ego in check because they’ve been turned into a “Discount Queen” to save a deal the Board of Directors were guaranteed would close? It’s not pretty… not pretty at all.
  • Limited Account Knowledge.  A CEO can’t take the time to go deep AND wide in large enterprise engagements or in complex sales scenarios to really know and validate economic and technical buyer influences. Nor are they postured to challenge incorrect presumptions.  Last but not least, managing an internal home pursuit team that doesn’t normally “play” together while leveraging limited internal resources… is a nightmare for all parties.
  • FUD (Fear, Uncertainty & Doubt)  A CEO who manages deals in competitive scenarios may be unintentionally promoting uncertainty and instability that translates in buyer code as “desperation.”
  • Alienation from the Bottom.  Do W-2 salaried, director-level business and technology managers (generally the evaluators) feel comfortable transparently interacting with a self-employed, soon-to-be mega-rich CEO? Some do and some don’t. Want to risk it?

The net: Just because you can sell… it doesn’t mean you should.  Mr. CEO thank you. No, really… I mean it. THANK YOU.

-Chris