Always Be Closing: A Life in the Trenches of Tech Sales
Making the Nut: A Salesman’s Survival Memoir
Chapter One: The Gospel of the Close
The movie Glengarry Glen Ross doesn’t just open with a sales contest. For me, it opened a doorway—one I would walk through again and again across decades of software sales, armed with a pitch deck, a quarter-end quota, and the kind of determination that only comes from knowing your mortgage depends on getting to yes.
You see, my life didn’t begin in a cubicle or on a conference call. It started in the shadow of grit. My father and uncle were both in sales before the term "tech stack" even existed. Theirs was a world of ashtrays and Rolodexes, where every day was a pitch and every night a reckoning. The phrase "making your nut" was passed around like gospel—it referred to the old traveling shows that had to pay a fee just to unlock their wagon wheels. No nut, no journey. In our world, the lock was quota. The nut was survival.
And survive we did. On charm, mostly. On gut instinct and a good haircut. I fell in love with that world before I could even spell "CRM." At eight years old, I was role-playing as a traveling salesman, hawking fake wares to imaginary clients. I’d walk around the house with a clipboard, pitching a nonexistent product with the intensity of a man trying to sell air conditioning in Antarctica. I learned fast that silence was pressure. A pause, deployed properly, could crush the will of even the most skeptical buyer. That’s why God gave us two ears and one mouth—so we’d shut up and listen twice as often.
My grandmother, God rest her, taught me the handshake—firm, focused, and never limp. "Nobody buys from a dead fish," she’d say. "Unless it’s halibut. Halibut’s pricey."
Chapter Two: CRM Confessions and Commission Carnage
Sales isn’t a career—it’s a confession booth with a dashboard. And the CRM is your priest, jury, and executioner. I spent years typing in carefully curated optimism, praying the forecast gods would smile upon me. But here’s the dirty secret: the numbers always lie. Sometimes for you. Often against you.
There’s an art to fudging forecast data just enough to get more resources without tipping into full-blown fiction. In one job, I created my own internal color code: green meant locked, yellow meant I was still working the political angles, red meant I had absolutely nothing but charisma. The problem was, management didn’t care about nuance. They wanted green. Green meant lunch meetings, green meant QBR clout, green meant survival.
Then came the carnage. Quarterly bloodletting. I watched as peers—some who could sell a ketchup popsicle to a woman in white gloves—were fired for missing quota by five percent. The same people who were hailed as heroes during the last sales cycle now had security walking them out the front door with a manila envelope and a coupon for LinkedIn Premium.
I kept my job, but I started losing something else: belief. Not in the product—I could sell sand in the Sahara if it came with a free dashboard—but in the system. The CRM wanted loyalty. The commission plan demanded sacrifice. And somewhere between my 43rd red-eye and my 900th rejection, I realized I wasn’t chasing success. I was being chased by failure.
Chapter Three: The Watch, the Car, and the Illusion of Arrival
In sales, symbols matter. The car, the watch, the wine you pretend to enjoy at company dinners. I remember buying my first Omega Speedmaster after closing a $600K deal. I wore it like armor. It wasn’t about telling time—it was about telling a story: I’m someone who wins.
And the car? A German import leased at 3.9% APR, washed religiously. I knew a customer once who said, “I don’t trust a guy with a dirty car or a clean desk.” So mine was always spotless. On the outside. On the inside, it was a rolling office-slash-crisis center. It smelled like stress and stale coffee. A place where I rehearsed pricing objections out loud until I believed them myself.
But here’s the truth. No watch, no car, no rooftop dinner in Vegas ever fills the hole left by chasing something for so long that you forget why you wanted it. The illusion of arrival—of having “made it”—is the great mirage of sales. It’s always just one deal away. One promotion away. One magic deck away. And then it moves.
Chapter Four: The Great Betrayal (or, Why Your Manager Isn’t Your Friend)
There’s no knife like the one your own manager holds.
We were tight—weekly one-on-ones, war stories over whiskey, mutual admiration about our “strategic alignment.” Then one Thursday, I was asked to forward my pipeline report. I didn’t think much of it. By Monday, the same manager was on a call telling me my “fit” was no longer aligned with leadership’s vision.
Fit. Not performance. Not ethics. Just... fit. Like I was a pair of pants that didn’t match the blazer anymore.
That betrayal taught me the golden rule of sales: everyone is loyal until there’s a board slide involved. I wasn’t even angry. Just stunned at how transactional the loyalty had become. I once closed $2 million in a quarter. Six months later, I was replaced by someone younger, cheaper, and better at using emojis in Slack.
Chapter Five: The People We Build
I came back from that. Not by selling harder—but by mentoring better. I began investing in people the way I used to invest in prospects. I coached reps who thought they weren’t cut out for it, only to watch them become team leads. I taught one guy how to handle silence—he went from 60% to 140% of quota in under a year.
There’s a deep, unspoken joy in seeing someone else win because of something you passed down. It's not scalable, it won’t make you rich, and it rarely shows up in Salesforce. But it’s the real ROI.
One woman I mentored went on to lead an entire territory. She sent me a photo of her first big deal inked. I still keep it in my inbox. That was the first time I realized I’d finally closed the most important deal of my life: helping someone else believe they belonged.
Chapter Six: Final Pitch
.The thrill. The terrifying freedom of knowing it’s all on you.
Sales is noble. It’s not glamorous. It’s real. It teaches you how to be brave with your voice and exact with your silence. It teaches you that rejection doesn’t kill—it clarifies. And it teaches you that people will disappoint you more often than systems ever will.
And yet, I’d do it all again. Clipboard in hand. In front of a stranger. With only a product and a handshake between us. Because, as my uncle once said—“Youth is wasted on the young.”
He was wrong. Sales isn’t.
Chapter Seven: The Anatomy of the Pitch
The perfect pitch is like jazz—structured enough to land, loose enough to improvise. In my prime, I treated demos like theater. Each click was a cue, each slide a script. I watched my audience’s pupils, not the bullet points on my deck. The truth of the room doesn’t live in the presentation—it lives in the micro-reactions.
Yes, I sold software. But what I really sold was redemption. Your workflow sucks. Here's why. Now here’s how I’ll make you a hero at the next board meeting. The product was the vehicle. The pitch was the gospel. And if you couldn’t preach it like your rent depended on it, you had no business asking for budget.
Eventually, pitching became performative. Pre-recorded demos. Canned scripts. All sizzle, no steak. So I went analog. I treated every pitch like a first date: ask better questions, tell sharper stories, know when to shut up. Software doesn’t close. People do.
Chapter Eight: Death by Enablement
Enablement sounds empowering, right? Wrong. It’s a factory for slightly upgraded PowerPoint drones. I once sat through a two-day session titled "The Language of Value." I left with a booklet, three acronyms, and no recollection of how to be human.
They gave us flashcards—FUD, BANT, MEDDIC. Tools, they said. But tools are only helpful if you know when to drop them. The best reps I’ve ever worked with knew when to go off-script. Because real selling lives off-script.
After one particularly brutal training, I skipped the next three. My win rate went up. Correlation isn’t causation, but causation’s got a tell.
Chapter Nine: Life at 30,000 Feet
The airport life is seductive when you’re young. You feel important. You have status. You have TSA PreCheck and a lanyard with a bar code. But you’re also lonely. I once woke up in a Courtyard Marriott and couldn’t remember what city I was in until I opened the minibar and saw a regional IPA.
You miss birthdays. You forget what your kid’s favorite cartoon is. You see your spouse more on FaceTime than in your kitchen. The irony of selling connectivity tech while becoming emotionally disconnected? Not lost on me.
Chapter Ten: The Slide That Lied
Slide decks are crime scenes. The number of deals murdered by one too many slides could fill a true crime podcast. I once had a VP add a roadmap slide mid-demo. “Just show them what’s coming,” he said. The prospect wanted reliability. We gave them fantasy.
So I made my own decks. I weaponized case studies. Quoted real names, real revenue, real failures turned into fixes. If someone asked, “What does this look like in the wild?” I had receipts.
Flash doesn’t renew contracts. Clarity does.
Chapter Eleven: The Unicorn Myth
Every sales org has the Unicorn Deal. The one that’ll blow the number wide open. Mine was a Fortune 50, multi-year, multi-million-dollar chase that had more stall tactics than a congressional hearing. I built custom pricing models. Flew coach to conferences I couldn’t afford. Sent custom whiskey kits to procurement.
It never closed.
But what I learned was this: unicorns don’t exist. The deals that feed your soul are smaller, sneakier, and show up disguised as minor leads. I’ve had $45K deals lead to $5M partnerships. And I’ve had $5M prospects ghost me faster than a Tinder match after a typo.
Chapter Twelve: Epilogue in Real Time
I’ve stepped back. Not out, but back. I coach. I consult. I remind people why they started. I teach young reps that “no” isn’t rejection—it’s recalibration. I help veterans remember that they’re not what they close, they’re who they build.
Sometimes, I still run pitches in my head like lullabies. Old habits, old hymns.
Sales is an absurd religion, built on hope, pressure, and projected confidence. But I believed in it. Still do.
Because, in the end, we’re all just trying to be heard. Understood. Remembered.
And that, my friends, is always worth the close.
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Having worked in securities and insurance sales, I know of what thee speaketh!