Is Now a Bad Time To Get Into Sales?

Wes Schaeffer
3 min readAug 16, 2023

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There’s never a bad time for a wimpy salesman to get into sales and coast!
There’s never a bad time for a wimpy salesman to get into sales and coast!

Question:

Is now a “bad time” for a “highly skilled laborer in Tech” who “made my career through relationships.. strategic problem solving.. and hard work.. a lot of hard work” “to get into sales?”

Answer:
There will always be a need and a spot for a good salesperson.

Selling is much more programmatic and precise than people understand.

My first paid sales training client back in early 2007 was an architect who was branching out on his own.

We worked on his outreach process and scripting and we role-played some scenarios and he killed it because he stuck to the program.

Most salespeople get into trouble when they start winging it and thinking they’ll just get by with their charm, wit, good looks, golf swing, and expense account.

The problem many salespeople get into — especially men who want to “solve” and “fix everything right away, and especially sharp technical people — is they jump right into solution mode and start giving advice and recommendations and going for the close before the prospect feels heard and understood.

It doesn’t matter that you are right, which you probably are.

Until the prospect feels heard and seen and understood, their guard is up and they are defensive and suspicious of your recommendation, even if it’s the perfect thing for them.

But you have all of the advantages, coming from a tech background because a salesperson without your background will take years to come even close to your knowledge and experience, whereas if you just have some patience, take a genuine interest in your prospects, learn how to ask good, engaging questions, and provide good answers without giving the farm away, you can excel in sales.

There will always be tech companies booming and busting, so take your time to investigate the founders and leaders and talk to the salespeople at the company to get the truth.

There are always private equity firms buying up good companies and looking to grow.
Businesses related to automotive repair and home remodeling/repair will probably do well for a long time.

I think there’s a push for “made in the U.S.A.” after the shock of COVID-induced supply chain constraints, so see who’s making a move like that. (I’m headed to Maine Friday for a week for a Brazilian Jiu-Jitsu camp put on by Origin, which is exploding in this space. They make BJJ gis, rash guards, etc. and now boots, jeans, hoodies, etc., as well as supplements such as protein powders and energy drinks. It’s anecdotal, but another is ToeHold. He’s small, but he sells $400 to $1,000 flip flops and is booming.)

With this background — “highly skilled laborer in Tech…relationships..strategic problem solving.. and hard work.. a lot of hard work” — you have what it takes to thrive in sales.

Good luck.

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Wes Schaeffer

Read great books. Create great content. Sip great whiskey. Sell or be sold.