About 10 years ago I was sitting at a bar in an unremarkable U.S. metro area, I honestly don't remember where...

I was having a beer with a colleague who had flown in from the Boston area. If I remember right a company All-Hands or Sales Kick-Off (SKO) had brought us to this particular bar, a poorly lit dive where we were taking full advantage of the company-sponsored, open tab by ordering a half dozen pints of craft lagers, each.

A few drinks in, the colleague, who was in his late 40s was sharing stories and lessons from his 25-year career selling technology.

If you ever get a chance to hear war stories from someone who sold tech since the 90s, I highly recommend it. It's hard to Fathom how enterprise deals got done in a pre-SaaS world (imagine scoping out space for server racks at a company's headquarters as part of your sales cycle 🤯)

Eventually, the conversation led to him sharing the story of closing a $4M enterprise software deal with HP, a deal that earned him a 7-figure commission check and jumpstarted an upward trajectory in his career.

I seized the opportunity to ask him what he thought the secret was to closing that size of a deal and achieving that level of success in tech sales. At the time I was early on in my career journey and unable to wrap my head around a 7-figure commission and W2, hell at that time I don't think I'd even had a 6-figure year yet.

Here's what he said to me:
​"Jesse, no matter what, you can't give up. You have to keep playing the game. Eventually, you'll get an opportunity to win big, but the key is to never give up."

As you can imagine I called bullshit on his response. No way could that be it, right? Surely it was his mastery of MEDDPICC or some other selling methodology or maybe he was a savvy negotiator, made more cold calls than everybody or had a Challenger personality. Maybe he had some secret formula for multi-threading execs, right? In my mind, there just had to be something more to his successes than not giving up.

I have no doubt he had some serious skills, but according to him, one could dedicate every waking hour to building sales skills or business acumen and still miss out on huge financial success in their sales career if they decide give up too soon.

I've had many years to think about this conversation and I've never forgotten it. In hindsight, he was right.

You can't give up.

In 2019, I almost gave up.

I was completely burned out having just exited my second failed stint at an early-stage startup. Only a year and a half before, I'd walked away from a cushy middle management role at a Silicon Valley Unicorn leaving behind both stability and equity to pursue startup sales glory.

I was over it.

I was unemployed and considering a major career change and as the months went by, I watched my savings start to disappear. I made a plan to get out of tech entirely and do something completely different - Healthcare, Higher Ed, Public Service... Anything.

But then, opportunity knocked one more time...

At my lowest point with minimal job prospects and a drained savings account, I noticed an InMail from a recruiter with an intriguing opportunity and a chance to give enterprise sales one more shot (this time at what felt like the right company).

I remembered the conversation with my colleague over drinks at the bar years before: No matter what, you can't give up.

I decided to give it just one more go with the hope of redeeming myself in my tech sales career and taking another shot at making life-changing commission checks (mostly so I could build back my savings back up).

Looking back, I'm SO glad I didn't give up.

The years since have been the most successful of my career in terms of earnings, job satisfaction and performance.

After deciding not to give up, I:

• Closed my largest enterprise deal (that story is here)
• Achieved multiple successive quarters of attainment (which funded the downpayment on my house)
• Developed my repeatable enterprise sales operating process
• Got acquired by a FAANG company (and was lucky enough to cash out my stock options)
• Worked with some amazing leaders and mentors
• Launched Sales Players - the podcast, this newsletter and my coaching business​

Now just imagine if I'd decided to throw in the towel back in 2019...

What's the point of sharing all of this?

I'm fortunate to be able to connect with many a Sales Player through this platform and lately, I've noticed that the outlook for many is bleak right now.

It's been a tough few years in tech (particularly for sellers) and 2025 is off to an interesting start. A slow economy, challenging job market, and lots of FUD (Fear Uncertainty Doubt), makes selling a lot harder right now.

I think this has led many to settle for mediocre results or even worse consider quitting the game of sales altogether.

Don't do it!

I share this because I know in this line of work it can sometimes feel like everyone else has it all figured out and you're just an imposter.

I share this to reassure you that there will always be ups and downs, in selling tech, it's a feature, not a bug.

And despite what you may see on your LinkedIn feed, most of us are still trying to figure things out.

I share this because you might be just one deal, one interview round or one big quarter away from life-changing success.

For now, focus on what you can control and most importantly:

Never give up!​
-JMW

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