Four years ago, I published one of the most popular articles I’ve ever written: So You’re Telling Me There’s a Chance: The Joy of Buying Technology. I repost it from time to time and continue to draw reactions. Since four years have passed, I thought I might be due for a follow-up article on the subject of the buy-sell dynamic in enterprise technology.

In this article, I’m not going to discuss annoying sales tactics and gimmicks. I’ve covered that before. In this article, I’m going to drill into a more complex issue, which is how salespeople interact with the hierarchy of IT.

The engineer

Quite a while ago, I was an engineer. I loved working on technology and was frustrated that I could barely get the attention of technology vendors because I didn’t hold the budget. They didn’t want to talk to me. They wanted to talk with a decision-maker that had the authority to spend the company’s money.

I recall several occasions where senior leaders several layers above me made technology-buying decisions and handed them down for us lowly engineers to implement. Often, they bought inferior products and sometimes purchased extra products that we didn’t even need.

At the time, I blamed the management above me for not carefully consulting the engineers every step of the way. Now, I understand that sales practices are also a big part of that problem. More on that later. At the time, I vowed that when it was my turn to lead from the top, I’d do it differently.

The mid-level manager

Not long after this, I became a manager with a budget. Vendors started flocking to me to vie for their slice of it. Over years of experience, I became competent to work on complex deals. I kept my promise to always involve my engineers in process. Nothing I bought was a surprise to my team.

Fortunately for me, I’ve always had the benefit of working for a very supportive and empowering boss. I was given great latitude to negotiate and close deals.

Unfortunately for me, I often held a title (such as IT Manager or IT Director) and for whatever reason, this simply wasn’t impressive enough for the salespeople at the technology companies. Several times, I’ve had the unpleasant experience of a salesperson going over my head.

The technology executive

For a little over a year now, I’ve held a title that adequately pleases most salespeople. I am a Vice President. That means salespeople no longer go over my head. However, that also means that my span of control is such that I cannot possibly be the only deal-maker for my organization. The world works too fast for centralized control. I delegate and support my management team on most commercial deals. That’s not just because I’m a good empowering leader, it’s because there is simply too much going on for me to be the chokepoint.

It’s ironic. Now that I hold the ideal position (from the salesperson’s perspective), I no longer have the time or context to do anything with it. Most of the time, when salespeople reach out to me, I refer them to my management team or engineers.

The problem

Here’s the real problem as I see it. Technology salespeople choose to interact with enterprise corporations with a baseline assumption that all of the power is at the top and everyone in the middle and bottom are unempowered worker bees.

As far as I am concerned, that’s an entirely outdated assumption.

A new way forward

I’ve started to experience a new way of working with a small subset of technology companies. These companies don’t target executives, they target engineers. Since engineers don’t have any buying authority, they distribute their products freely.

Then, there’s usually some threshold where a commercial agreement for the enterprise makes sense. By that point, the engineers are already hooked and are easily able to demonstrate the value to their decision-makers higher up.

I love this approach. I’ve predominately found it in the DevOps and Cloud-Native ecosystems, but it could work everywhere.

These salespeople have a default assumption that they are dealing with an empowered leadership culture. While I know this isn’t safe to assume everywhere, this is where we all should be heading.

A corporate executive’s perspective

I’ll be the first to admit that I am not a salesperson. I’ve never worked for a commission or managed a quota. I have no idea whether or not this change in approach will actually make you more money. This is simply a customer’s perspective. I’ve been working in enterprise technology for nearly 22 years and I’ve been buying technology products for about 15 of those years. I’ve experienced a lot of ineffective sales approaches and I think it can be a whole lot better.

Enterprise technology buyers, do you think we’re on to something? Technology salespeople, win over my engineers. Then we’ll talk.

Still digging my sales articles? I have one more for you here: “I Love Your Blog. Why Won’t You Respond to My Sales Call?“

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