Author: Gary Miller

Gary Miller here, wondering why I thought selling software would be easier than this.

So there I was last month, three months deep into what looked like my best deal of the quarter. Sarah, the operations director at this growing logistics company, absolutely loved our business software. We’re talking about a $180K deal – not life-changing money, but solid enough to make my numbers look respectable.

Sarah had been burned by their current system for two years. During our video calls, she’d practically light up talking about how our software would solve her team’s workflow problems. “Gary, this is exactly what we need,” she told me after our third demo. “I can already see my people being so much more productive with this.”

I thought I was golden. Sarah had budget approval, her team was excited, and we’d worked through all the technical requirements. I was already mentally spending my commission when she called me on a Tuesday morning.

“Gary, we have a problem,” she said, and I could hear the frustration in her voice. “Corporate just informed us that our parent company signed a enterprise-wide deal with your competitor last week. We have to use their system instead.”

Apparently, while Sarah and I were having our productive conversations, the corporate folks three states away were making their own software decisions. They’d bought a different solution for all their subsidiaries – something that sort of did what Sarah needed, but not nearly as well as our software.

“This is ridiculous,” Sarah continued. “Your solution is perfect for what we do here. Their system is built for companies twice our size with completely different needs. But I have no choice – it’s coming down from corporate and there’s no budget for anything else.”

I tried everything I could think of. Could we position our software as an add-on? Nope, corporate wanted standardization. Could we wait six months and revisit? Maybe, but Sarah would be stuck with the other system by then and wouldn’t have budget to switch. Could we talk to someone at the parent company? Sarah gave me a contact, but that person never returned my calls.

The worst part? Sarah kept apologizing. “I’m so sorry, Gary. I know how much work you put into this. Your software really is better for what we need.” She genuinely felt bad about wasting my time, which somehow made it worse than if she’d just ghosted me.

Two weeks later, Sarah messaged me that corporate had pushed back the implementation of their chosen system by four months due to “resource constraints.” So now she’s stuck with her old, broken system even longer, waiting for a solution that won’t work as well as ours would have.

I moved on to other prospects, but I still think about that deal sometimes. Sarah found the perfect solution for her team’s problems, had the budget and authority to buy it, and genuinely wanted to work with me. But none of that mattered because someone in a corporate office made a different decision.

And that’s business software sales for you – sometimes the best deals die in conference rooms you’ll never see.

Gary Miller here, typing this from my home office slash kitchen table, still processing what happened on yesterday’s video call.

So I’ve been working this deal for three months – mid-size manufacturing company, about 800 employees, perfect fit for our business software. The kind of prospect that makes you think maybe this sales thing isn’t so bad after all.

My contact Sarah, their operations director, absolutely loves what we can do for them. We’re talking inventory management, supply chain visibility, the whole nine yards. She’s been walking me through their current process, which involves three different systems that don’t talk to each other and about fifteen spreadsheets that get emailed around daily.

“Gary, this would solve everything,” she tells me on our third call. “We’re wasting probably twenty hours a week just moving data around manually.”

Music to my ears, right? She’s already run the numbers – our $180K solution would pay for itself in eight months just from the time savings. Her team is excited, her boss is on board, and she’s ready to move forward.

Then comes the call I should have seen coming.

“Gary, I have some news,” Sarah says, and I can hear it in her voice before she even starts. “Corporate just informed us they’ve already purchased something for the whole company. We have to use their solution.”

Apparently, while Sarah and I were having our productive conversations about solving real problems, the parent company was off making deals with some massive software vendor. One of those everything-for-everyone solutions that promises to handle every business process known to mankind.

“Does it actually do what you need?” I ask, already knowing the answer.

“Well, it does inventory management,” she says. “Sort of. It’s more complicated than what we’re doing now, honestly. And we’ll need to hire two people just to run it. But corporate says it’s what we’re using.”

I try to salvage something. “What if we could show them a side-by-side comparison? Demonstrate the cost savings?”

Sarah laughs, but not in a good way. “Gary, they’ve already signed a three-year contract. The decision’s been made. I’m sorry – I know we’ve both put a lot of work into this.”

So there I am, watching a perfect deal disappear not because our software wasn’t good enough, not because the price was wrong, not because I didn’t build the right relationship. It vanished because someone three levels up in a corporate tower decided to buy software they’ll never actually use.

The kicker? Sarah messages me two weeks later saying the corporate solution is a disaster and asking if there’s any way we could work together in the future. Maybe when their contract is up in three years.

I thanked her and filed it under “follow up in 2028.”

That’s B2B sales in 2025 for you – sometimes the best relationships and perfect solutions still lose to corporate politics and bulk purchasing decisions.

Gary Miller here, and I’m starting to think our demo system has a cruel sense of timing.

So there I was yesterday, fifteen minutes into what should have been a straightforward product demo with a potential $300K client. The kind of call where everything’s lined up perfectly – the decision maker’s finally available, budget’s approved, and they’re ready to see our business software in action.

I’m walking through our inventory management features, feeling pretty good about things. The prospect, Janet from a mid-sized manufacturing company, is asking all the right questions. “Can it handle our seasonal fluctuations?” Yes. “Does it connect to our existing accounting system?” Absolutely. “How quickly can we get reports?” Real-time, Janet. Real-time.

Then I click to show her the reporting dashboard, and nothing happens. The screen just sits there, spinning. You know that little loading circle that basically means your day is about to get complicated?

“Just give me one second here,” I say, doing that thing where you click refresh seventeen times like it’s going to magically fix everything. Still nothing.

Turns out – and I only learned this after twenty minutes of troubleshooting while Janet waited patiently on the video call – our demo system was completely overloaded. Apparently, three other sales reps were running demos at the exact same time, plus our marketing team was doing some kind of stress test. The whole thing just buckled under the pressure.

Janet was surprisingly understanding. “These things happen,” she said, though I could see her checking her phone. We rescheduled for today, but you know how it is – that momentum is gone. The magic moment where they’re ready to buy right now? That doesn’t usually come back.

I spent the rest of the afternoon on messages with our technical team, trying to figure out how to prevent this from happening again. Their solution? “We’re working on a scheduling system for demos.” Great. In 2025, we need to schedule time to show our software because too many people want to see it. That’s either a really good problem or a really stupid one.

The kicker? This morning I get a message from Janet saying they’ve decided to “explore other options” and won’t be rescheduling. Fifteen years in business software sales, and I’m still getting beat by a spinning wheel.

My manager asked what we could learn from this. I told him maybe we should invest in demo systems that can handle more than three people at once. He said he’d “circle back” on that. I love how we can build software that manages entire supply chains, but we can’t figure out how to let four sales reps show it off simultaneously.

The worst part? I checked our system usage report, and we’re paying for demo capacity we’re not even using properly. We’ve got the resources; we just can’t coordinate them. It’s like having a Ferrari that only works when no one else is driving.

So now I’m back to square one, looking for another $300K deal to replace the one I lost to our own success. And that’s business software sales for you – sometimes the biggest obstacle between you and the sale is your own product.

Gary Miller here, fresh off a call that went about as well as you’d expect when someone asks the one question you’re hoping they won’t ask.

I’m on a video call with Janet, the operations director at a mid-sized logistics company. Nice deal potential – around $150K if everything goes right. We’re forty minutes into what’s been a solid demo of our business software, and she’s nodding along to everything. Our workflow automation is solving their bottleneck problems, the reporting features are exactly what they need, and I’m thinking this might actually close before the end of the quarter.

Then Janet leans forward and asks, “So Gary, what kind of AI does your software have? Everyone’s talking about AI these days, and my CEO keeps asking about it.”

I feel that familiar sinking feeling. You know the one – when you realize you’re about to disappoint someone who’s been excited about your product for the last hour.

“Well, Janet,” I start, buying time while my brain scrambles, “we have some really smart features that help automate your processes…”

“But is it actual AI?” she presses. “Like, machine learning and all that?”

Here’s the thing – our software does have some automated features. It can sort data, send alerts when certain thresholds are hit, and even suggest workflow improvements based on patterns. Marketing calls these ‘intelligent features’ and ‘smart automation.’ But actual AI? The kind that learns and adapts and does all the stuff people see in the news? Not so much.

I take a breath and go with honesty. “Janet, I’m going to be straight with you. What we have are some really solid automation tools that can make your team more efficient. They’re smart in the sense that they can handle complex rules and conditions, but they’re not the kind of AI that’s going to write your emails or predict the future.”

She sits back in her chair, and I can see her enthusiasm cooling in real time. “Oh. Because our current vendor just added some AI features, and honestly, that’s part of why we’re looking at alternatives. We want to stay competitive.”

Of course they do. Everyone wants AI now, even when they don’t really need it or know what they’d do with it. I spend the next ten minutes explaining what our software actually does well – and it does a lot of things well – but I can tell the magic is gone.

The call ends with the usual “we’ll be in touch” and “need to discuss internally,” which in sales-speak means “thanks but we’re probably going with someone who has shinier buzzwords.”

After we hang up, I sit there staring at my screen, wondering if I should have just said yes and figured it out later. But then I remember all the deals I’ve seen go sideways because someone oversold what the software could actually do.

Sometimes being the honest guy means losing deals to whoever’s willing to promise the moon. But at least I can sleep at night knowing my clients won’t be calling me six months later asking why their ‘AI’ is just a fancy if-then statement.

And that’s business software sales for you – caught between what people want to hear and what you can actually deliver.