Gary Miller here, and my phone should probably just say ‘currently being ignored,’ because that’s what happened after I promised a client our business software would play nice with their entire digital ecosystem.
Last month, I was three weeks into what looked like a solid $180K deal with a manufacturing company. The CFO loved our numbers, the operations team was excited about the efficiency gains, and I was already mentally spending my commission check. Then came the fateful video call with their IT director.
“So this connects to our ERP system, right?” he asked. “And our inventory management tool. Oh, and our customer portal. Plus we need it to talk to our accounting software and that new analytics thing we bought last year.”
I nodded confidently because, honestly, everything connects to everything these days, right? “Absolutely,” I said. “Our software is designed to work with your existing systems.”
Big mistake. Huge.
Turns out their “existing systems” included software I’d never heard of, a custom-built tool from 2018 that apparently runs their entire warehouse, and something called “Kevin’s Excel thing” that somehow controls their shipping. When I asked our technical team about compatibility, the response was basically a very polite version of “absolutely not.”
The follow-up call was painful. “Well, we can connect to your ERP system,” I explained, “but the inventory tool would need some custom work. And Kevin’s Excel thing… well, that’s going to be interesting.”
The IT director’s face on the video call said everything. “So when you said it connects to our existing systems, you meant some of our systems, with additional work, at additional cost?”
I tried to salvage it. “Look, most companies go through a transition period. We can help you modernize your processes.” But I could see the CFO in the background shaking her head. Nobody wants to hear that buying new software means rebuilding everything else.
They asked for a detailed integration plan with timelines and costs. Three weeks later, after our technical team had basically written a small novel about APIs and data mapping, the quote came back at $240K plus six months of implementation work.
The client went quiet for two weeks. When they finally called back, it was to tell me they’d decided to “optimize their current systems first” and would “revisit this next quarter.” Translation: they found someone else who promised them the impossible, or they’re sticking with Kevin’s Excel thing.
I spent the next week updating our marketing materials to be more specific about what “seamless integration” actually means. Spoiler alert: it’s never actually seamless.
The thing about business software sales in 2025 is that everyone wants everything to work together perfectly, but nobody wants to pay for the work to make that happen. Some conversations never get easier, no matter how long you’ve been doing this.
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