Why I Changed Sides
I spent roughly 25 years working for vendors with narrow portfolios. The job was to hit a number, not necessarily provide the right solution for the client.
The seat I kept observing
For years I built and ran sales and channel programs for large firms like AT&T and Time Warner Cable as well as numerous smaller companies. That work put me across the table from my customers competing with other suppliers. Meanwhile, the agents and trusted advisors occupied a very different space and I envied their positioning.
What I noticed was the seat they were sitting in. They sat next to the client, representing their interests. They were not carrying one company’s product line into the room. They got paid when the client got something that worked, and they kept getting paid only as long as it kept working.
A more commonly known comparison may be that of a sports agent. The agent does not play the game. The agent knows the market, knows which teams are serious, knows what the contract language actually means, and is paid on the outcome the player gets. The player could negotiate alone. Almost none of them do.
That is the seat I wanted.
What a quota does to a recommendation
I want to be careful here, because this is not a shot at the reps for the companies in our technology ecosystem- I was one. Most of my colleagues then and the reps at those companies today were good at the job and honest about how their solution performed.
The problem is structural. A rep carries a quota, and that number is attached to one company’s portfolio. When a client’s situation lines up with that portfolio, everyone wins. When it does not, the rep has two bad options: walk away from the revenue, or find a way to make the fit look closer than it is. Everyone is trying to make a living in this world, so I get it. But those financial ramifications based on leveraged compensation packages inherently introduce a conflict of interest.
The part that bothers me most is that the client has to sift through the noise wondering if they are getting sound advice. The deck looks the same either way. The references are real. The pricing could be competitive. But there is no line on the proposal that says whether this was the right answer or the available one.
That is not a thing you can fix with better reps. It is a thing you fix by changing who the advice is coming from.
The homework nobody has time for
The bias on the supply side would matter less if the buy side had the capacity to thoroughly check it. Most do not.
IT organizations in the 500 to 5,000 employee range run thin by design. The people in them are very good at operating what they own. Procurement is a separate discipline, and frequently the only person in the building with real experience in it is the senior IT leader, who has limited time for thorough due diligence. So the search gets compressed. You take the three names everyone knows, build a comparison, and decide. That is not laziness. That is arithmetic.
What the top three does not tell you is the part that costs money later. Which of them is genuinely strong at your size, in your vertical, in your geography. Which one just lost the implementation team that built its reputation. Which one is quietly re-pricing renewals this year. Which one is excellent at the thing you saw in the demo and mediocre at the thing you will depend on in month seven. None of that is in an analyst quadrant or on a website.
We run procurements continuously, which means we are in these conversations when you are not. We leverage our vendor-agnostic subject matter experts whose job is not to protect anyone’s quarter. Who fits a situation like yours. Who is delivering right now. Who has slipped lately. Those are data points, and they accumulate only if you are in the market constantly.
One question does more work for me than any other, and I ask it at the end of almost every conversation: What haven’t I asked you today that I should have? It hands the other person permission to raise the thing my questions did not reach. A supplier’s rep is not often going to volunteer the detail that complicates their deal, and I understand why. My job is to find it anyway, before it becomes your new reality and nobody can remember who was supposed to have asked.
The two challenges after signature
Selling is the part of this business everyone pays attention to. Two things that happen after the signature get far less, and they are where I watched clients get hurt.
The first is implementation. A contract gets signed, the account team moves on to the next number, and the client is handed to a project coordinator who has forty other installs. Nobody who made promises in the sales cycle is still in the room when those promises have to come true. I have watched good decisions turn into bad outcomes entirely in that gap.
The second is the renewal. A client signs a three-year agreement, uses the service, and three years later gets hit with an auto-renewal for the same term because no one had flagged it in time to renegotiate. Meanwhile the technology got cheaper, the client’s headcount changed, and half of what they are paying for is not being used.
A renewal should mean a rate reduction or more value. Most of the time it means neither.
Right-sizing spend at renewal is work, and it is work that often reduces the supplier’s anticipated margin. There is no version of the vendor relationship where that work gets done enthusiastically. Somebody on the client’s side has to do it, and many IT teams do not have a person to spare.
Two years learning the other side
When faced with a crossroads: a position that was no longer the right fit and some health issues that were going to demand much of my attention, I started my first advisory firm. What I found out quickly was how much I did not know. I had deep knowledge of a handful of company portfolios and a channel’s mechanics, but the ecosystem I was now tasked with advising on was enormous.
With the health issues largely in the rearview mirror and the time to dedicate to a position, I went to work for a well-known technology distributor for about two years. That was a deliberate move. A distributor sits in the middle of hundreds of supplier relationships and the trusted advisor (agent) community. I wanted to hear all of those stories from the inside rather than from a sales deck. Which suppliers deliver what they say. Where the contract language bites. What a good implementation team looks like versus a name on an org chart.
Then I came back and rebranded the practice as Converge IP.
The goal is not the transaction. It is long-term stewardship: an industry insider on your side of the table through the selection, the implementation, the life of the contract, and the renewal after that. Back to the agent comparison: a good agent does not disappear at signature. That is where the work starts.
What this newsletter is
IT Dexterity comes out every Tuesday. It rotates through four things:
The Advisor’s Seat — what this work looks like from where I sit, including the parts I get wrong.
The SAO Framework — the method I use to inspect, select, connect and protect, written so you can run it yourself.
Vendor Reality Check — how the supply side actually works, so you can read a proposal with better eyes.
The Decision Dividend — what the numbers looked like when the work got done.
Every IT leader I talk to is resource-constrained. That is the condition now, not a bad quarter. The point of this newsletter is to put one usable thing in your hands each week that you did not have to go find.
If that is useful, subscribe. If you want to talk about something specific, book a Strategic Fit Call and we will find out in thirty minutes whether there is anything here worth your time.
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Vendor-agnostic analysis for IT leaders in banking, healthcare, and government. One piece a week. No vendor pitches.
Eric Pankonin · Founder, Converge IP · 30+ years in enterprise IT and telecom
