Average Sales Guy

If you’re looking for secrets to hitting 300% of quota, scaling your outbound to infinity, or becoming a sales ninja warrior, you’ve probably clicked the wrong link.

Author: Gary Miller

  • When Your Contact Forwards Everything to Everyone

    Gary Miller here, and if you think your job is complicated, try explaining software to people who don’t want it while managing a contact who thinks transparency means copying the entire company on every email.

    So I’m working this $180K deal with a manufacturing company that needs our inventory management software. My main contact, Sarah from operations, seems great at first. Responsive, asks good questions, understands the problem. Then I send her a simple follow-up email after our demo.

    Twenty minutes later, my phone starts buzzing. Sarah forwarded my email to five people: the CFO, IT director, plant manager, procurement guy, and someone called “Bob from logistics.” Each one wants to schedule their own call to “understand the solution better.”

    “Sure,” I tell Sarah on our next video call, “happy to talk with the team. Maybe we could do one group call?”

    “Oh no,” she says, “everyone has different questions. Plus Bob’s really busy and can only do Tuesdays at 7 AM.”

    Seven AM. On Tuesdays. For a guy who wasn’t even mentioned in the original project.

    So I start the rounds. The CFO wants to know why we’re more expensive than the system they looked at three years ago but never bought. The IT director spends forty-five minutes explaining their server setup that has nothing to do with our cloud-based software. The plant manager keeps asking if it works on his tablet, which I answer four times.

    Then there’s Bob. Bob from logistics joins the 7 AM call from what sounds like his car, eating something crunchy, asking me to repeat everything because he “wasn’t really involved in the earlier conversations.”

    After each call, I send Sarah a recap. She forwards it to the same five people. Who then reply with more questions. Which generates more meetings. The CFO wants a second call. The IT director needs to “loop in his team.” Bob’s now available Thursdays at 6:30 AM.

    Three weeks in, I realize I’m spending more time scheduling calls than actually selling. Sarah means well, but she’s created this feedback loop where every answer generates three new questions from people who weren’t paying attention the first time.

    The breaking point comes when the procurement guy – who’s been silent for two weeks – suddenly announces they need to “evaluate three vendors” and asks if I can re-do my entire presentation for his boss, who’s Bob’s cousin or something.

    I finally had to tell Sarah we needed to streamline the process. “Look, I’m happy to answer everyone’s questions, but we’re going in circles. Can we get the real decision makers in one room – virtual room – and hash this out?”

    Turns out the real decision maker was someone named Janet who nobody had mentioned. She wasn’t on any of the forwarded emails. We had one thirty-minute call, she said yes, and we closed the deal.

    Bob from logistics never did figure out what we were selling. Sometimes the best client relationship strategy is knowing when to stop managing all the relationships.

  • When Your Champion Gets Laid Off Mid-Deal

    When Your Champion Gets Laid Off Mid-Deal

    Gary Miller here, and you’d think after all these years I’d stop being surprised by how quickly things can fall apart in this business. But here I am, staring at a bounced email from my main contact at a $300K deal that was supposed to close next month.

    Sarah had been my champion at this manufacturing company for eight months. She understood exactly why they needed our business software – their current system was held together with spreadsheets and prayer. We’d done the demos, mapped out the implementation timeline, and she’d been walking it up the chain. Everything was moving along nicely.

    Then I get the dreaded LinkedIn notification: “Sarah Johnson is no longer at Manufacturing Solutions Inc.”

    Layoffs. Budget cuts. Restructuring. Pick your corporate buzzword – the result was the same. My champion was gone, and with her went eight months of relationship building and education about what we could do for them.

    So I do what any reasonable sales rep does – I start making calls. First to Sarah’s old number, which now goes to some generic voicemail. Then to the main line, asking to speak with whoever took over her responsibilities.

    “That would be Marcus in operations,” the receptionist tells me. “But he’s pretty swamped taking on extra duties.”

    I finally get Marcus on a video call two weeks later. Nice enough guy, but he’s clearly drowning in his expanded role. I start explaining our software and the project Sarah had been working on.

    “Wait, what project?” Marcus interrupts. “I don’t see anything in my notes about new software.”

    My heart sinks. Sarah hadn’t documented any of our progress. No internal emails about the business case. No notes about the demos. Nothing. It’s like eight months of work just evaporated.

    I try to rebuild from scratch. “Look, Marcus, your current system has some real gaps. Sarah identified several areas where our software could save you guys serious time and money.”

    “I’m sure she did,” Marcus says, “but honestly, with all these layoffs, we’re in cost-cutting mode. Any new spending is frozen until further notice.”

    The deal didn’t die dramatically – it just faded away like most deals do. Marcus was too busy keeping the lights on to think about improvements. The budget Sarah had been nurturing got reallocated. The urgency we’d built up disappeared with the person who felt it most.

    I kept in touch with Marcus, sent him some helpful resources, stayed on his radar. Six months later, when their old system finally broke down completely, he remembered our conversations. We ended up closing a smaller deal – $150K instead of $300K – but at least it was something.

    The funny thing is, Sarah landed at another company three months later and brought me in for a conversation there too. Sometimes your champion just moves to a different building.

    That’s the reality of business software sales these days – you’re not just selling to companies, you’re selling to people. And people change jobs, get laid off, get promoted, or just move on. Your deal is only as strong as the relationships behind it.

  • When Your Dream Client Gets Acquired Overnight

    When Your Dream Client Gets Acquired Overnight

    Gary Miller here, and sometimes I miss being able to just walk down the hall to complain to someone when everything goes sideways.

    So I’ve been working this deal for eight months. Good company, growing fast, perfect fit for our business software. We’re talking about a $300K deal – their inventory management system was held together with spreadsheets and prayer. I’d built real relationships with Sarah, their operations director, and Mike, the CFO. We’d done the demos, handled their objections, even got through procurement’s twenty-page vendor questionnaire.

    I’m literally preparing the final proposal when Sarah messages me at 7 AM: “Gary, call me. Something big happened.”

    Turns out they got acquired overnight. Some private equity firm swooped in, and suddenly my eight-month courtship is worthless. The new owners already have a preferred vendor – their portfolio companies all use the same system. It’s not even a competitor I know well, just some enterprise software that does roughly the same thing but costs twice as much.

    “I’m so sorry, Gary,” Sarah says on our video call. “I know how much work you put into this. But the decision’s already made. They’re standardizing everything across their companies.”

    Mike jumps in: “We fought for you, man. Showed them your proposal, explained how well you understood our business. But they’ve got existing contracts and volume discounts. It’s done.”

    Here’s the thing that really gets me – this wasn’t about our software being wrong or our price being too high. This wasn’t even about client relationship management or sales negotiation. It was just business. Some guys in suits decided to buy the company and everything I’d built became irrelevant in a conference room I’ll never see.

    I spent the rest of the day staring at my pipeline, wondering which other deals might evaporate tomorrow. That’s the reality of B2B sales in 2025 – you can do everything right and still lose to forces completely outside your control.

    The funny part? Two weeks later, I get a LinkedIn message from someone at another company in the same private equity portfolio. They’d heard about our software from Sarah and wanted to set up a demo. Apparently, word travels fast in those corporate family trees.

    So now I’m back to square one with a new prospect, explaining the same features to solve the same problems. The irony isn’t lost on me – I’m essentially competing against the system that killed my original deal. But that’s enterprise sales techniques for you: sometimes you lose the battle and accidentally position yourself for the next war.

    Sarah and Mike both endorsed me on LinkedIn and said they’d be references for future deals. In this business, that’s worth more than most people realize.

    And that’s business software sales for you – relationships survive even when deals don’t. Sometimes the best thing about losing is finding out who your real allies are.

  • When Your Client Wants Champagne on a Beer Budget

    Gary Miller here, fresh off a call where nobody could figure out how to unmute, and I just lived through every sales rep’s nightmare scenario.

    Picture this: I’m three weeks into what looked like a solid $200K deal with a growing company. Nice people, clear pain points, and they’re nodding along to everything I’m showing them. Classic mid-market opportunity, right?

    Then yesterday’s video call happens. The CEO jumps on – first time I’ve seen him – and starts rattling off his wish list. “We need advanced analytics dashboards, custom reporting for each department, automated workflows, and oh yeah, can it connect to our existing systems? All fifteen of them.”

    I’m thinking, this guy wants enterprise-level features. That’s fine, we can do enterprise. I start explaining our premium package, walking through the advanced capabilities, building up to the investment level.

    “Sounds perfect,” he says. “Our budget is $50K.”

    Fifty. Thousand. Dollars.

    I actually had to mute myself for a second. This is like walking into a Mercedes dealership and asking for the S-Class with a Honda Civic budget. The features he wants would cost us more than $50K just to implement.

    So I do what any reasonable sales rep does – I try to bridge the gap. “Let me show you how our standard package could work for you now, with a path to upgrade as you grow.”

    But he’s not hearing it. He’s got this vision of his company running on enterprise software, and somehow he thinks startup pricing applies. His team is sitting there looking uncomfortable, probably knowing this conversation was coming.

    I spent the next twenty minutes doing mental gymnastics, trying to find a middle ground. Maybe we could phase the implementation? Perhaps some features could wait? What about a longer contract for better pricing?

    Nothing. He wants everything, now, for basically nothing.

    The worst part? He keeps saying “Well, your competitor quoted us $45K for something similar.” Yeah, similar if you squint really hard and ignore about 80% of the functionality you just asked for.

    Finally, his CFO – who’d been quiet this whole time – speaks up. “Maybe we should revisit our requirements and see what’s actually essential for year one.”

    Thank you, voice of reason.

    We ended the call with me promising to “see what I can do” – which is sales speak for “I’ll talk to my manager, but we both know this isn’t happening at that price.”

    Here’s the thing about selling business software in 2025: everyone’s seen the fancy demos, everyone knows what’s possible, and everyone thinks it should cost what software cost in 2015. They want Tesla features at Toyota prices.

    I get it, budgets are tight. But wanting enterprise capabilities while paying startup prices is like expecting first-class service in economy. The math just doesn’t work.

    Now I’m crafting the delicate follow-up email, trying to reset expectations without losing the deal entirely. It’s all about finding that sweet spot between what they want, what they need, and what they can actually afford.

    Some days I think about selling something simple, like staplers. But then again, someone would probably want a titanium stapler for the price of plastic.

  • When Your Biggest Competitor Goes Free Overnight

    When Your Biggest Competitor Goes Free Overnight

    Gary Miller here, and I’m convinced some people make decisions by throwing darts at a board. Last month, I learned this lesson the hard way when TechCorp bought out my biggest competitor and decided to give their business software away for free.

    I’m sitting in my home office on a Tuesday morning, coffee getting cold, when my phone starts buzzing like crazy. Three different prospects texting me variations of “Hey Gary, saw the news about DataFlow going free – can we talk?”

    DataFlow was our main competitor for years. Good software, similar features to what we sell, but they always charged about 20% more than us. Suddenly overnight, they’re free. Not cheap – free. As in zero dollars.

    My first call was with Jennifer at MidCorp Manufacturing. We’d been working on a $180K deal for four months. She gets on the video call looking apologetic but determined.

    “Gary, you know I like you and your software, but free is free. My CFO is asking why we’d pay anything when DataFlow does basically the same thing for nothing.”

    I tried explaining that free software isn’t really free – there’s implementation costs, training, support issues. But try selling that to a finance team that just sees a big fat zero in the price column.

    The next two weeks were brutal. I watched three solid deals evaporate faster than my patience during a Monday morning team meeting. Prospects who were ready to sign suddenly wanted to “explore all options.” Translation: they wanted free stuff.

    Here’s what nobody talks about with free software – it’s still a pain to implement. I started hearing back from some of these companies within a month. Turns out when you don’t pay for something, the support isn’t exactly priority service. One guy told me he’d been waiting two weeks for someone to return his call about a basic setup question.

    The real kicker came when I got a call from Jennifer again. MidCorp had spent three weeks trying to get DataFlow working with their existing systems. Their IT guy was pulling his hair out, their team was frustrated, and their CFO was starting to understand that “free” can be the most expensive option.

    “Gary, can we revisit our original proposal? This free thing is costing us more in lost productivity than your software would cost us in three years.”

    We ended up closing that deal at full price, plus some additional services to help them transition from the mess they’d created. But I lost two other deals permanently to companies that decided to stick with free, even when it wasn’t working well.

    The whole experience taught me something important about modern sales. People still want to believe in magic solutions – whether it’s software that installs itself or competitors that suddenly give everything away. But business software isn’t about the price tag. It’s about solving real problems for real people.

    Six months later, half those “free” customers are quietly shopping for alternatives. Turns out you get what you pay for, even in 2025. Some lessons never go out of style.