by Jerry Gregoire

The Hardest Job in IT Is Sales, Not CIO

May 01, 20027 mins
Relationship Building

CIOs get 70 percent of their information about new and quickly evolving technologies directly or indirectly from salespeople, according to a study done for The Wall Street Journal. Scary, but not surprising. It’s no secret that I’ve never been real fond of technology salesmen or their endless shenanigans, but still, I have to give these folks their due. As hard as a CIO job seems sometimes, it’s difficult to conceive of anything harder than selling software. Imagine making your living selling broken stuff?code with more bugs than a cathouse mattress. Or having to routinely promise features that don’t yet and may never exist (a practice known as overhanging the market), at prices that bear no earthly resemblance to the product or service being rendered.

There’s a book I think you and all of your managers should read called How to Sell Technology: Technology Sales Is a Premeditated Sport, by Paul DiModica. It’s not Ulysses and it’s not likely to be made into a screenplay anytime soon, but it’s a worthwhile read for a couple of reasons. First, it goes a long way toward explaining why salespeople do some of the weird things they do, and second, this book can be a valuable tool for teaching your folks how to sell technology projects within your company. Oh, and while you’re at it, give a copy to your administrative assistant. I’m sure he will get a big kick out of the section on the six ways to “get past the gatekeeper,” particularly the “intimidation method.”

I happened across How to Sell Technology on the Internet. DiModica’s website ( promotes the book like an infomercial, promising to reveal “secret proven formulas” and “dramatically increase your income and closing ratio,” complete with glowing and untraceable testimonials and a free bonus if you order the manual within the next 24 hours (24 hours from when, it didn’t say). Expecting the worst, I paid my hundred bucks, and in a couple of weeks, the 120-page softcover, ring-bound manual arrived. On the front, a youngish looking man (who I assumed at the time was DiModica), wearing a David Byrne-size jacket, leaps into the air and points at the sky. That evening I pulled up a chair in my workshop and flipped to the first section, “Perception Is Reality.” What a way to start, I thought. I set the book down and went to get a beer.

It’s kind of a shame they didn’t take a more dignified approach to marketing this book. My guess is that it will be overlooked by a lot of people who will assume that the contents are just as hollow as the website. In fact, the book deserves a lot more respect than that. DiModica opens with an admonishment that ought to hang on the wall of every CIO’s office. It reads: “If you can’t pick up the phone and cold-call, or handle the objections from a tough chief executive officer of a large company or the drilling probing of a small business owner because you are afraid, then you should get out of technology.”


Sadly, many great ideas have gotten lost in the explanation. The ill-prepared messenger, kicked in the teeth so often he could headline in Branson, eventually learns it’s safer just to turn in the direction of the skid.

Using case studies and exercises, the book goes on to describe an approach to selling technology and big projects that is at once creepy in the way it manipulates situations and language, and inspired in its directness, simplicity and packaging. Some of the material will probably be a little disturbing for those of us who’ve spent most of our working lives on the receiving end of the pitch. And some of the tactics DiModica recommends are shortsighted, to say the least. But these are problems the reader can easily spot and correct.

DiModica and I met in a restaurant in Buckhead, Ga., to talk about his book. He is not the youngish man on the cover. If selling computer software and services were an Olympic sport, Paul DiModica would be tested for steroids. Smart, earnest, hyper, a little long-winded and a genuinely nice guy, I barely said more than hello before he launched into a soliloquy on his book that threatened to break 30 minutes. Sensing he was about to take a breath, I interrupted.

Gregoire: Paul, are you selling all the time? Do you ever stop selling?

DiModica: I don’t know. Probably not.

Why are so many of the salespeople I’ve come across so hard to put up with?

Most salespeople have no clue how to sell. The most important thing we teach in our program is respect for the senior executive and his time. There are 262,000 technology companies in the United States. So let’s say 10,000 of them think they have something to sell you. That’s a lot of traffic coming to your desk?mail, phone calls. Now, let’s say I’ve got a great new company with an unbelievable new technology. I will never get to you unless I can create great communication, address your problems (pain) and intrigue you enough to want to speak with me for 20 minutes. I’ve got to show respect, be succinct and accurate, get in, get out and not waste anybody’s time. Most salespeople don’t know how to do that.

So what are the top mistakes people make when selling technology?

Well, first of all, most of them come to sell instead of listen. They’re not prepared, and they tend to shoot from the hip. Second, they don’t know what they’re selling.

They don’t understand their product?

No, it’s deeper than that. They don’t understand the value of what they’re selling and, consequently, can’t explain its value. And third, they sell technology instead of a solution.

Do you think we underappreciate technology salespeople?

Oh, yeah! They’re unbelievably underappreciated. It’s because of the pressure?the churn and burn. Buy cycles are always different and longer than sell cycles, and it’s always a question of how to make quota. The pressure is tremendous. CRM systems have raised the visibility of what we do to the point where every minute of every day, every meeting, every forecast is constantly being evaluated.

So why would anyone want to be a salesman?

Good question. The pay is good, if you’re good at it. It’s independent; you have the ability to be on your own. It’s ego too?it’s for people who like to win.

Ah, Yes, Winning

Many of the IT folks we all know are far more comfortable with processes than people. Two of the most important yet often overlooked soft skills we should develop in our up-and-coming managers are the ability to address an audience without staring at their shoes and the ability to explain (sell) worthwhile projects to management.

Years ago, fed up with wasting time and money on presentation skills seminars, I began signing my people up for acting classes at the local community theater. At graduation, each was expected to take a role in a public performance during that year’s theater season, for which the entire department would always turn out. It did wonders for their confidence and poise. (I can’t say it did much for the community theater’s longtime director, who, rumor has it, was so deeply traumatized he was last seen wandering shoeless in North Dakota.)

The next step, had I thought of it at the time, would have been a week or so studying DiModica’s program.

Trust me. Buy the book.