About Gary Miller & Average Sales Guy
Hey there, I’m Gary Miller
After fifteen years in B2B software sales, I’ve learned one thing for certain: most of us are just trying to figure it out as we go along. I’m not a sales guru, I don’t have a magic formula, and I definitely don’t have all the answers. What I do have is a collection of stories from the trenches of enterprise software sales – the good, the bad, and the hilariously awkward.
What This Blog Is About
Average Sales Guy is where I share the real, unvarnished truth about selling business software in 2025. You won’t find motivational speeches or “10 Ways to Close Every Deal” lists here. Instead, you’ll get authentic stories about:
- Real sales situations that every B2B rep recognizes
- Modern challenges like video calls that freeze at the worst moment
- The human side of enterprise software sales
- Authentic experiences from someone who’s lived through it all
My Background
I’ve been selling enterprise software to mid-market and large corporations for over a decade and a half. My typical deals run around $100K, with the good ones hitting $200K+, and once in a blue moon, I’ve seen the mythical $1M+ deal.
I’ve adapted to the modern world of remote selling, video calls, and instant messaging, but I still remember when you could just walk down the hall to talk to someone. I understand enough about APIs, integrations, and modern tech stacks to sell them effectively, but I’m not technical – I’m a people person trying to help other people solve business problems with software.
What Makes This Different
This isn’t another sales blog promising to make you a superstar. It’s stories from someone who’s genuinely average – competent, experienced, but realistic about the challenges and absurdities of modern B2B sales.
Whether you’re a junior rep just starting out or a veteran with 10+ years under your belt, these stories are for anyone who’s ever:
- Had a demo crash at the worst possible moment
- Watched a deal disappear for reasons that made no sense
- Dealt with procurement teams that seem to exist just to complicate things
- Tried to explain why your software is different from every other software
- Wondered why your best prospects sometimes just vanish
The Reality of Enterprise Software Sales
Selling business software in 2025 means navigating:
- Remote relationships built through screens
- Complex buying committees that seem to grow every week
- Security reviews that cost more than the software itself
- Integration requirements that sound simple until they’re not
- Budget processes that change faster than the weather
But it also means helping businesses solve real problems, building genuine relationships (even through video calls), and occasionally landing deals that make all the frustration worth it.
What You’ll Find Here
Every few days, I share a new story from the field. Sometimes it’s about deals that went sideways, sometimes it’s about unexpected wins, but it’s always honest. These aren’t polished case studies – they’re real experiences from someone who’s been in the trenches and lived to tell about it.
You might recognize yourself in these stories. You might laugh, cringe, or think “yeah, that’s exactly how it goes.” That’s the point. Sales can be isolating, especially when you’re working remotely, and sometimes it helps to know that other people are dealing with the same absurd situations.
A Word About “Average”
When I call myself the “Average Sales Guy,” I don’t mean mediocre. I mean real. Most of us aren’t sales superstars closing million-dollar deals every quarter. We’re professionals who work hard, care about our clients, and try to do right by everyone involved. We have good months and bad months, deals that make us look brilliant and deals that make us question our career choices.
There’s dignity in being average. There’s authenticity in admitting that this job is hard, that we don’t always have the answers, and that sometimes the best response to a difficult situation is to find the humor in it and move on.
Why I Share These Stories
Because every sales rep has felt like they’re the only one dealing with impossible prospects, broken software, or deals that disappear for no reason. Because sometimes you need to hear that other people have been through the same thing. Because laughing about the absurdity of it all is better than crying about it.
And because, despite all the frustrations, I still believe that what we do matters. We help businesses find solutions to real problems. We build relationships across industries and time zones. We turn strangers into trusted advisors, and we help companies grow.
That’s not average at all. That’s pretty remarkable.
Connect
If these stories resonate with you, if you’ve got your own tales from the sales trenches, or if you just want to commiserate about the latest procurement obstacle you’re facing, I’d love to hear from you. Leave a comment on any post, and let’s share the experience.
After all, we’re all in this together – trying to make sense of an industry that’s constantly changing while staying true to the human connections that make it all worthwhile.
Welcome to Average Sales Guy. Pull up a chair, grab a coffee (or something stronger), and let’s talk about what sales is really like.