Author: Gary Miller

Gary Miller here, and you’d think after all these years I’d stop being surprised by how complicated “simple” requests can get.

So I’m on this video call with Brian, the Chief Information Officer at this international logistics firm based in Dallas. Big operation, trucks and warehouses all over the place, the kind of company that makes the world actually work. We’re in their annual strategy session, and Brian’s got his IT and Operations teams on the call.

The budget’s solid – we’re talking $500K to $750K range, which is exactly the kind of deal that makes my month. Our software would genuinely help them track shipments better, and Brian gets it. He’s nodding along, asking good questions, and I’m thinking this might actually be straightforward for once.

Then Brian drops the bomb: “This all sounds great, Gary, but it has to work with everything we already have. Our warehouse management system, our accounting software, our customer portal, and especially the tracking tool our biggest client demands we use.”

I’m thinking, okay, how hard can this be? We connect to lots of stuff. So I start going through our standard integrations list, feeling pretty confident.

“What about your current warehouse system?” I ask.

“Custom built in 2018,” Brian says.

“Okay, and the accounting software?”

“It’s this specialized logistics thing. You probably haven’t heard of it.”

He’s right, I hadn’t. But I keep going. “And the customer portal?”

“Another custom job. Oh, and it all has to sync with the client’s tracking tool in real-time because they check it constantly.”

I’m frantically messaging our technical team while trying to look calm on camera. The responses I’m getting back are not encouraging. Lots of “we’d have to build that” and “that would require custom development.”

Finally, I have to be honest. “Brian, I need to level with you. We can probably make most of this work, but it’s going to require some custom development. That’s going to add time and cost to the project.”

The Operations director jumps in: “How much time and cost?”

I’m doing math in my head, and it’s not pretty. “Probably another four months and… maybe $200K?”

You could hear the air go out of the room, even over the video call. Brian’s looking at his screen like I just told him his dog died.

“So we’re talking almost a million dollars and eight months total?” Brian asks.

“That’s… probably realistic,” I admit.

The call ended politely, but I knew it was over. They went with a smaller solution that worked with their existing systems right out of the box. Not as powerful as ours, but it actually worked with what they had.

Turns out in 2025, having the best software doesn’t matter if it can’t talk to the dozen other systems your client already depends on. Sometimes the perfectly adequate solution that plays nice with everyone wins over the amazing solution that needs everything rebuilt around it.

Gary Miller here, and I’ve learned that the word ‘easy’ is relative to everything except software implementation, where it apparently means ‘we’ll figure it out as we go.’

Last month I was working with Michael, the CTO at a growing real estate company in Minneapolis. We’d been through their quarterly planning meeting where they’d mapped out this massive digital transformation – we’re talking a $1.5 million investment to overhaul how they handle everything from property management to client relationships. Operations, Procurement, Sales, Finance – everyone was on board.

Michael had done his homework. He’d compared us against that European company with their crazy aggressive pricing, ran all the numbers, got buy-in from every department. Three months of calls, demos, and presentations. When we finally got to the contract signing, he looked me in the eye and said, ‘Gary, this is exactly what we need. How quickly can we get this running?’

‘Implementation is pretty straightforward,’ I told him. ‘Our team will handle the heavy lifting. You’ll be up and running in 90 days.’

Famous last words.

Two weeks later, I get a video call from Michael. He’s got that look – you know the one. Like he’s been staring at spreadsheets for six straight hours.

‘Gary, we need to talk about this implementation timeline,’ he starts. ‘Your technical team just sent us a 47-page document listing everything we need to do before they can even start the setup.’

Turns out ‘straightforward’ meant they needed to clean up fifteen years of data spread across twelve different systems, get approval from their parent company’s IT security team in three different time zones, and somehow coordinate schedules between our implementation team and their people who were already stretched thin from their regular jobs.

‘The Finance team is asking why we need to hire two temporary data analysts,’ Michael continued. ‘And Operations wants to know why they can’t use the system for the first month while we’re migrating everything over.’

I’m sitting there thinking about all those smooth demos where everything worked perfectly with our clean sample data. Reality had other plans.

‘Look, Michael,’ I said, ‘I know this feels overwhelming right now. Every implementation has surprises. The important thing is that we’re committed to making this work.’

He laughed – not the good kind. ‘Gary, my CEO just asked me why we’re spending seven figures on software that won’t actually help us for six months.’

We ended up extending the timeline to five months, bringing in extra consultants, and having weekly calls with all four departments to manage expectations. The project eventually worked – they’re happy with it now – but those first few months taught everyone involved the difference between buying software and actually using it.

Michael and I still laugh about it during our quarterly check-ins. He’s become one of my best references, actually, because he tells prospects the truth: great software is worth the headache, but plan for the headache.

And that’s business software sales for you – the demo is always perfect, but real life has other plans.

Gary Miller here, wondering why every startup that says they’re “not looking to sell” somehow ends up with new owners three months later.

So I’d been working this deal since last summer – a growing fintech startup, about 200 employees, perfect fit for our business software. The CEO, Sarah, was fantastic to work with. We’d had maybe six calls over four months, really building something solid. She understood exactly how our software would help them scale their operations, and we were talking about a $180K deal to start, with expansion potential as they grew.

I’m thinking this is going to close by end of quarter. Sarah and I have that good working relationship where she’s actually returning my messages, her team is engaged, and the budget conversation went smoother than usual. You know how rare that is these days.

Then I get a LinkedIn notification that stops me cold. Sarah’s updated her profile – she’s now “Former CEO” and there’s a press release about the acquisition. Some big financial services company bought them out. Completely blindsided me.

I reach out to Sarah immediately. She’s apologetic but realistic: “Gary, I’m sorry, but everything’s on hold. New ownership means new priorities, and honestly, they already have enterprise software relationships locked in.”

Of course they do. The acquiring company probably has contracts with our biggest competitor that go back years. All those months of relationship building, all those discovery calls where we mapped out their exact needs – none of that matters to the new owners.

I ask Sarah if there’s anyone I should connect with on the new team. She gives me a contact, but warns me: “They’re probably going to want to standardize everything on whatever they’re already using. It’s just how these things work.”

She’s right, naturally. I reach out to the new guy, and he’s polite but clear: they’re consolidating all their subsidiaries onto their existing platform. Doesn’t matter that our software is a better fit for what Sarah’s team was building. Doesn’t matter that we’d already done half the implementation planning. Corporate standardization trumps everything.

The kicker? Three weeks later, I see Sarah’s started a new company. She messages me: “Hey Gary, we should talk in six months when we’re ready to look at business software again.”

So now I’m back to square one with Sarah, except she’s got no employees and no budget yet. Meanwhile, that $180K deal I was counting on for Q4 just evaporated because of market changes I couldn’t have predicted or controlled.

This is the reality of business software sales in 2025 – external disruptions can kill your best deals overnight. You can do everything right, build great relationships, understand the customer’s needs perfectly, and still lose because of forces completely outside the sales process.

At least Sarah and I have a good relationship for her next company. In this business, sometimes that’s all you can salvage when the market shifts under your feet.

Gary Miller here, after spending my morning on back-to-back video calls with a client whose industry just got turned upside down by new federal regulations.

Six months ago, I was working this beautiful $300K deal with a mid-sized financial services company. They needed our business software to handle their compliance reporting – nothing fancy, just solid automation that would save them about 40 hours a week of manual work. The kind of deal that makes sense for everyone.

My main contact was Sarah, their compliance director, and we’d built a great relationship over monthly video calls. She knew exactly what they needed, had the budget approved, and we were just waiting for legal to finish the contracts. I was already counting this one as closed.

Then last Tuesday happened.

Sarah messaged me at 7 AM: “Gary, we need to talk. Emergency call in an hour?”

Turns out the government dropped new regulations that completely changed how financial services companies have to handle compliance reporting. Everything we’d been planning for six months? Useless. The requirements were so different that our software couldn’t even handle half of what they now needed to do.

“It’s like we ordered a car and now we need a boat,” Sarah said on our call, and I could hear the exhaustion in her voice. “The new rules don’t even make sense yet. We’re all trying to figure out what compliance even looks like now.”

I spent the next three days on calls with our product team, trying to understand if we could modify our software to handle the new requirements. The answer was basically “maybe, in eighteen months, for triple the price.”

Meanwhile, Sarah’s company put a freeze on all new software purchases while they figured out their new compliance strategy. My $300K deal didn’t just get delayed – it evaporated. They literally couldn’t buy what we were selling anymore because the rules changed overnight.

The worst part? Sarah felt terrible about it. She kept apologizing during our final call, like it was somehow her fault that Congress decided to rewrite industry regulations without asking her first.

“Gary, you’ve been great through all of this,” she said. “When we figure out what we actually need, you’ll be my first call.”

Which is nice, but doesn’t help my quarterly numbers. And honestly, by the time they figure out their new requirements, there will probably be three new vendors offering exactly what they need.

I’ve been in B2B sales long enough to know that deals fall through for all kinds of reasons – budget cuts, personnel changes, competitors swooping in. But having your entire deal category eliminated by regulatory changes? That’s a new one, even for me.

Now I’m back to prospecting, explaining to my manager why my forecast just dropped by $300K, and hoping the government doesn’t decide to regulate any of my other prospects’ industries this quarter.

Some days you’re selling business software, other days you’re just watching the world change faster than anyone can keep up with.