IN THIS EDITION
This edition is how to get non-boring results by following a quite boring process.
De-glorifying real $100k commission checks.
Let’s get into it.
Article: 5 tips from legit $100,000 commission checks
The sales reps who became multi-millionaires overnight
And more…

SELLER’S SECRETS

5 tips from legit $100,000 commission checks
This week, a simple question was posed:
“Who here has pulled a $100k+ commission check, and how did you do it?”
A few hundred replies later, an opportunity for sales people to flex turned into a particularly valuable source of truth from many unique perspectives.
Stripped out the bragging and the same handful of truths kept surfacing.
Here are the five that showed up the most:
Live in the accelerator zone
Almost every monster payout in the thread had the same shape. The rep was already past quota when a big deal happened to land, so it dropped into accelerators instead of base rate. One guy said the exact same deal in a fresh year would have paid him half, maybe less.
So in most cases, it has nothing to do with hunting unicorns. Stay far enough ahead that when one wanders in, you collect 3x-5x times on it instead of base rate.
Your comp plan matters more than your deal
One rep closed $6M and got paid $10k. Another capped out at $75k no matter how big the deal got. All the while someone selling the right product banked $796k on a single close.
Same effort yet wildly different outcomes. Before you fall in love with a logo, know your accelerators, your caps, and how your plan actually pays. The deal you're proudest of can easily be punished by an unfavorable comp plan you didn’t catch early on.
The big check is almost never one deal
Read closely and most of these are pileups. Two or three deals closing the same month. Multiple plan elements maxing at once. A strong quarter landing on top of an already strong year.
The perfect storm usually comes from a bunch of good closes converging while you're sitting in accelerators, not just from “one perfect deal”. You can engineer that by keeping volume up instead of praying for a whale.
Patience and a book beat job-hopping
The biggest checks came from people who had been somewhere a while. One rep called the same client for eight years before they signed. Plenty pointed to renewals and a residual book as the real long game instead of chasing new logos.
The reps switching companies every two years kept missing the window. You don't simply inherit accelerators or a book of business that can push out $100,000 checks. Most are built to be that from someone who deserves it.
Save it, the feeling fades fast
A lot of people who hit the big check said the high wore off quickly. You move the goalposts on yourself and it becomes the expectation. A few had witnessed coworkers get wrecked by sudden money like this.
The ones who stayed happy oftentimes treated the check like a tool. Paid things off, banked the rest, kept living normal. It changes your bank account without having to change you.
The pattern behind these five tips is boring on purpose. There’s no magic tricks being done on their sales calls It just seems to boil down to smart positioning, hard work, and time in the game.
Easy enough yeah?
What's been your highest commission check?

COMMUNITY WIN

Umesh was an agency owner who realized he liked the sales portion of his business more than the ongoing fulfillment of services/client relationship.
So he dialed in on the part he likes — the selling, but as a WFH contractor.
He’s taking 2 inbound sales calls per day, with leads a company generated 100% for him.
Extremely part-time. Plus he’s got a $5,000/mo draw in the event that the company doesn’t book people with him.
He now has leverage to do what he wants outside of selling.
Because as a %-based contractor, nobody can legally obligate you to do anything aside from take the calls that are booked.
Less meetings, less reporting, less admin.
In and out, collect your check and go.

LIVE FROM THE SALES FLOOR
Recent Events
A crazy recap of sales in 2026 so far (LinkedIn)
555 responses to “why are you in sales?” (Reddit)
$60b acquisition, sales reps multi-millionaires overnight (X)
Tips + Tricks
Make your cold calls impossible to hang up on (YT)
Founder red flags to seek out before you commit to them (LinkedIn)
Other Stuff
Reps discuss earning $100,000 commission checks (Reddit)
They have a 28% win rate with this signal-based outbound method (X)
How to engineer your own luck systematically (X)

OUR SPONSOR

This week’s sponsor is Two-Piece Tuesday from TSSC.
Every week, we share 2x open 1099 WFH sales roles for free.
We break down how to source + perform deep DD on them.
It’s completely different from a salaried W2 sales role (given the heavily performance-based nature).
It’s incredibly important you know how to avoid bad offers.
Click here if you’d like to receive it for free!
This week:
$16,000/mo Closer role: Tax mitigation through Airbnb service
$7,000/mo Setter role: AI-enabled college test prep services

(plus a sneaky application link for one of them)

GET BETTER
Want the hiring secrets behind 1000’s of sales hires from top sales recruiters and managers?
Check out Hired: The Secret Manual.
40 questions, 12 partners, sub-60 minute read. There’s nothing else like it, we promise.

BEFORE YOU GO
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