Everything one rep learned in 30 years of sales
Originally posted by a retired salesman on r/sales. Condensed and lightly edited.
A retired salesman posted his entire 30-year playbook on r/sales. Top year over $800K. Out at 51. It's the most honest thing we've read about the craft — so we condensed it to the lessons that hit hardest. His words, lightly edited. Read the original →
Here's everything I learned in 30 years of sales. My top year was over 800K. I'm retired now.
Never turn down a job offer.
Doesn't matter what it is or how much you don't want it. Come up with a number and a counter. Would you do it for 500K? If they can't afford you — that's their problem, not yours.
Find the best rep and make them your mentor.
Not a wiki for every little question. Lunch once a month. Come prepared, take notes, say thank you. Some people genuinely want to teach. Find them, and don't waste their time.
Sell a territory, not one-offs.
One-off sales are grueling — a numbers game that burns you out. A territory is a different animal: a long-term relationship. I called on some customers until the decision-maker retired. I had 20-year relationships with many of them. I had actual employee badges for a few.
Keep it tight, then get out.
Do the business first — sort their emails, write your notes before you walk in. Save the kid's soccer practice and the daughter's wedding for the wrap-up. And if you get them to really, truly belly laugh — leave. Exit stage right.
Respect their time like it's money.
If you ask for three minutes, end in three minutes. The reps who don't? Customers start looking for the escape hatch the second they sit down. Don't be that person.
Use a pen.
Get a notebook and write things down in front of them. I don't know what it is — customers love it. They feel like the president. Pull out a phone and they don't know if you're taking a note or browsing Tinder. That's what their kids do to them.
Do the follow-up in the lobby.
Walk out, sit down, open the notebook, and do it right there. When the customer gets your email three minutes after you left, that's the impression that earns you every future project. Bonus: you've got less to do that night.
Cold-calling? Smile at the front desk.
Walk up, big smile, and just say: "Here's what I do, and I have no idea where to go or who to talk to." She'll usually take your hand, make the introductions, maybe hand you a slice of pie. That's her job.
When you can't get the meeting, FedEx the letter.
I couldn't get to a CEO I wanted. Did my homework — found out he sat on the board of the Boy Scouts. Wrote a short letter asking for 20 minutes and closed with: "If you don't think I delivered anything of value, I'll donate $200 in your name to the Boy Scouts." Sent it FedEx so it's the first thing on his desk and his assistant won't pre-screen it. Works for job applications too.
Learn the Landlord Rule.
Friendly, nice, accommodating — but not friends. This is business. Don't gossip. Don't drink at work functions. Things get weird with management when you're making 3X what they make. Don't be surprised if you're never invited into the management club. You're the one keeping the lights on.
CRM won't teach you to sell.
It's an HR tool, and mostly a waste of time. They'll fire you for lying in it or for not working — and they'll absolutely use it to move your quota. Do it if you must. Find your own way too.
Own your mistakes.
If you aren't making them, you aren't working. Own up, ask what you can do to make it right, and do it. Sometimes you have to break things. Ask for forgiveness later.
Fight for your customers.
A warehouse VP once told me he wasn't going to ship something a customer needed. We got into it. I hung up, called the company owner, told him to hold the line, then pulled the VP back on and made him explain it to the owner himself. Shipped in ten minutes. If your company punishes that, find another company.
Find your number.
This was never really about selling. Chase the uncapped commission. Keep a fat cash reserve. Invest early and like crazy. Every $1 million saved throws off about $40K a year at a 4% draw. Find your number, and figure out how to get there from here. The sooner you get there, the sooner you do what you actually want.
You don't own this thing.
The company owns it, and it can end any minute. One thing is certain the day you start a job: one day you won't work there. Realize that on the front end and get to work. Save the money. The more you pack away, the less stress you carry — and somehow, the less stress you carry, the more you sell. IDK why it works like that.
Good luck. Godspeed.
Why we're running this on the Polenta blog: half of it is reps you can actually rehearse — the three-minute open, the front-desk line, the FedEx pitch, the fight you have to win. That's exactly what we built Practice Studio for. The other half is just true. — The Polenta team