Sales loneliness, GTM engineers, and how to sell like Steve Jobs
The Briefing
Stories and news from the last month
1. Why Breaking into Sales Just Got Way Harder
My take: The average new hire is now 42 years old. Companies are prioritizing experience over potential. If you're breaking in, you need proof you can execute—side projects, consulting gigs, anything that shows capability. Doing the job will help you get the job.
2. GTM Engineers Won't Survive 2026
My take: GTM Engineers aren't going away this year. Enterprise companies will bring them in-house. SMBs will put them on retainer. Someone still has to orchestrate AI across your GTM motion until it gets easier to use (it’s coming). It's the same evolution RevOps went through - started as consultants fixing broken systems, then became essential infrastructure.
3. Being a "People Person" Won't Save Your Job
My take: Being a "people person" was never enough—it just looked that way when demand was easy and products were simple. Now that acquisition is hard and products are complex, you need both technical chops and commercial sense. If you only have one, you're done.
How to Sell like Steve Jobs
Last week I shared this as best thing I heard from the week.
Here's a few highlights with some color commentary of my own:
1. Use Simple, Unique Words
Jobs intentionally used simple but weird words because they stick.
His examples:
"crummy"
"uuuugly
“it screams (speed)"
Corporate language gets ignored, unusual language gets remembered.
2. People Remember Stories and Maxims
Jobs knew that specs and statistics don't stick in people's minds - stories do.
Examples:
Told the story of Apple starting in a garage (humanized the brand)
"Stay hungry, stay foolish" (became a life philosophy for millions)
Data informs. Stories persuade. Maxims get repeated.
3. When Presenting Use images - Minimal Words
Jobs' slides were the opposite of most corporate decks.
His approach:
showed a picture of the MacBook Air fitting in a manila envelope
displayed "4GB" in massive font with nothing else on screen
Stop filling slides with text. Show them what you mean.
4. Make Your Idea Repeatable
Jobs obsessed over boiling his pitch into a single line.
Examples:
“1,000 songs in your pocket"
“The world’s thinnest notebook"
If your pitch can’t be summarized in a sentence, the buyer won’t remember it.
And if they don’t remember it, they won’t repeat it.
5. Reframe Objections, Don’t Fight Them
Jobs didn’t argue against objections, he changed what they meant.
Critics:
“Apple’s market share is tiny. Only 5%.”
Jobs’ response:
"BMW has 5% market share too and yet no one thinks they’re at a tremendous disadvantage because of it.”
Reddit Post of the Week:
Sales has always been you vs. you. Remember:
50% of prospects won’t open your emails
~ 85% of your convos won’t lead to meetings
~ 90% of your calls won't get answered
~ 97% of your prospects won’t reply
Fear and inability to adapt is why most people fail.
The Best Thing I Heard This Week:
This is a guy who knew he was going to pass the background check.
P.S. Consulting Offer
Last year I helped three Series A+ companies accelerate sales growth.
Common problems they had:
Scaling from founder-led sales to predictable revenue
Growing outbound sales and rep development
Building a partner channel from the ground up
If you're interested, hit reply and let's talk.
Chris is a Director of Sales
TSG
P.S. I reply to all emails.