There are few aspects of my professional life that I enjoy less than evaluating enterprise software. Granted, my company sells enterprise software, and I’m in charge of marketing it, so I get the irony here.

But while enterprise software vendors increasingly focus on user experience, we are sorely deficient in prospect experience.

The problem starts like this: I make contact and explain my interests (usually in detail), and then schedule a meeting with someone I presume to have experience with the software. Knowing that everyone’s time is valuable, I do my homework. I do research. I prepare a list of questions. If my questions involve anything more than the basics, I send them ahead of time, just to make sure I give my sales contact the time needed to prepare.

And then comes demo day.

Access to Business 'Intelligence'

When it comes to preparing for a sales call, today’s sales professionals have it easy. They can research a prospect’s company and industry, and they can even see a roadmap of each prospect’s experience just by checking LinkedIn. In theory, salespeople should be so well prepared for each call that it’s spooky.

What’s spooky, however, is how some of these people remain employed. Granted, some LinkedIn profiles are incomplete or inaccessible publicly. Mine is neither of those things. My LinkedIn profile is so complete that close friends have learned things about me by reading it.

I would think that preparing for a call would be something a sales rep would want to do in the interest of saving time. After all, if I’m evaluating a replacement CRM for my company, I don’t need someone to sell me on the value of having a CRM.

Sticking to the Script Instead of Reality

Even with the “how to sell to me” roadmap I offer, I still get “the script” rather than a conversation. It’s like walking up the counter at Subway and saying, “Hi! I’d like a 6-inch turkey on wheat, toasted,” only to hear:

“Did you want foot-long or six inch?”

“Six inch”

“What kind of meat?”


“And what kind of bread?”


Then, once the sandwich is complete, you awkwardly mention that you asked for it to be toasted, knowing it’s far too late and there really isn’t any point in mentioning it other than, perhaps, saving some poor soul who comes after you from suffering cold bread.

But lunch is a six-inch sandwich, not a six-figure investment. In time, one learns to simply walk up to the counter and say hello. Eventually, the script starts and lunch ensues.

Enterprise salespeople, on the other hand, should be able to do more than follow a script, or respond to conversation keywords, as if they were the pooches of Pavlov. Enterprise salespeople should be able to listen and formulate intelligent responses. Instead, what I more frequently experience is akin to, “for my speech about scalability, say ‘scalable’; for my speech on ROI, say ‘budget’ or ‘investment’ or simply wait until the end of my presentation.”

Age vs. Experience

My company, Picturepark, boasts a management team with a combined experience tenure of more than 100 years. By contrast, collaboration software maker Podio boasts a team with an average age of 30.

Is there some sales advantage in prospects knowing that a significant percentage of your workforce is still — you know — sort of figuring things out? 

Steve Jobs was once a young visionary. But do the math: Jobs did his best work -- his most influential and culture-shifting work — only after he became an old man. Until there was Old Jobs, Apple was merely a technology company always on the fringe, and often gasping for breath. Further, making a point of having a “young” workforce is the yang to the yin of saying, We’re not old, therefore we’re better. Aren’t there laws against saying these sorts of things?

To be fair, experience isn’t a reliable measurement of value. But at least it suggests some level of commitment and industry memory.

A colleague has been selling digital asset management (DAM) systems for 20 years. While he would be the first to admit that he doesn’t know all there is to know about digital asset management, one has to assume that within 20 years, he’s learned a thing or two. More importantly to his prospects is that he can now quickly connect the dots between requirements and solutions. He doesn’t need to waffle between what’s possible and what’s doable, because he’s been around long to enough to know that if you sell the wrong system to the wrong prospect, it does no one any good -- especially the vendor who sold it.

Could someone with only a few years’ experience selling DAM systems have the same instincts? I suppose it’s possible. The problem is that most of my colleague’s counterparts at other companies don’t even have a few years’ worth of experience.

Send Me Your Best and Brightest

While recently evaluating software for deployment across my company, I received email from a sales rep for the company.

Agreeing to a call, I provided every last detail I could think of in order to make our call more efficient. I detailed my company’s plans for using the software, and I even outlined my personal experience with similar software. My goal was to make sure this rep knew I wasn’t a newbie, and that he knew I was a serious, qualified prospect. He assured me that he knew his software well, and that he understood my questions and requirements.

Below are some highlights from our call:

I asked if it was possible to build and use controlled vocabularies for data entry.

Yes, he said. I could do that using JavaScript.

When I asked if he knew what a controlled vocabulary was, he said he did and that it had to do with controlling things in the UI.

Next question: Was there any way to use Outlook with the system.

Yes, he said. He led me on a trip around his company’s website. He meticulously explained each section as if there was some connection between what I was seeing and world peace. All the while, I assumed we were headed to some secret page that explained the use of Outlook with his product. Eventually, we landed on his developer program page.

“You can easily build that with our API!” he explained with the excitement of a child who had discovered proof of magic’s existence.

I didn’t know which point to argue first: that he was suggesting that a marketing director use an API to build an Outlook integration, or that he claimed it would be easy for me (or anyone) to do so.

Realizing this call was going nowhere, and figuring I might as well have some fun, I asked him to demo the API to me so that I could see how easy it would be for me to use. He changed the subject to how email was really an old technology and that we would be able to entirely avoid using it once we had his software.

Learning Opportunities

“What about all the prospects and customers we have who don’t use your product?” I asked, ignoring my impulse to try cry out about the absurdity of his comment.

“You can easily add them all to the system!” he said.

I asked how I would go about adding a collection of contacts that sat squarely in the mid-five figures. He showed me how to add a contact -- one contact.I asked if there was, perhaps, some more automated way to add tens of thousands of contacts.

“That’s a great feature request!” he said. “But I think you’ll find you no longer need email.”

“You contacted me via email,” I reminded him.

He changed the subject again.

I asked next about bulk editing data in the system. You know, select x number of records, and adjust field values en masse. Fortunately, he explained, this was easy. He fumbled around in the system for a while until he landed on the report page.

“You can get those values here,” he claimed.

I explained that my goal was not to get those values, but to change those values. He said that we were now just arguing semantics.

At this point, I politely explained that I was ending the call because I wasn’t confident that I would be getting answers to any of my remaining questions.

I contacted his company to ask to speak to someone else. I told them about my experience with this rep and how I felt it reflected on their brand.To their credit, they seemed concerned. I was told a more knowledgeable rep would contact me to start over.

I couldn’t wait.

The wonderful thing about this second rep was that she could admit when she didn’t know something. The downside, of course, was that she played this card often. In my 72 hours demoing her product, I had configured an instance that was beyond her understanding. What was supposed to be her demo session quickly turned into my training session.

Let me say that this software is not complicated, it doesn't require the involvement of an engineer in order to make it work. And my questions were simply about the availability of features to accomplish specific tasks -- they were either available or they were not.

Unlike rep #1, this rep sensed my mounting frustration. She admitted that rep #1 was actually more experienced than she was, but that even he had been with the company only three weeks.

And there's the showstopper: Why were these people doing enterprise systems sales calls after only a few weeks? I couldn’t have been a more qualified prospect had I paid in advance.

What would have closed the deal was not the youthful exuberance of these two sales professionals, but the experience of someone like my colleague who could have connected my requirements to his software’s capabilities and offered useful ideas when a match couldn’t be made. Instead, I got not one but two different reps whose information was so laughable that I seriously considered starting a “Software Sales Reps Say the Darndest Things” blog. (That idea isn’t off the table.)

Don’t Get Off of My Lawn

Let me go on the record saying that I hold no bias against younger members of the workforce any more than I favor those of more advanced years. (At least no bias of which I’m consciously aware.) In fact, a nice, diverse workforce can not only be a good thing, it can be a fun thing.

I’m just about the oldest person at my company. My youngest coworker is one third my age. And while there are generational gaps that become apparent at our company, including coworkers not always knowing how to deal with the Old Man (Yes, coworkers, I know you feel this way and I still love you), I consider the diversity to be an asset.

As a marketer, I watch how “these kids today” do things. I see what’s important to them, and take note of what motivates them. I also know that the people who are writing checks for our six-figure DAM solutions are not likely members of the Teen Wolf fan club, so I’m not quick to discount the value of more senior employees -- you know, like those in their 30s and 40s.

But when I endure a miserable prospect experience at the hands of younger professionals, I can’t help but think that, in time, and with a little experience, they’ll get better.

Of course, by that time they’ll be old like me.

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