Softer Market Means Rocky Times Ahead in Tech Sales

Because I’m a headhunter, you’re probably not surprised I’ve been hearing about layoffs all year. It reminds me of the first recession I ever experienced. Looking back, it certainly wasn’t the worst recession I’ve recruited through (thank you, 2008!), but it was something I’d never been through before, and it shaped my perspective.

So pull up a seat, and let’s get into the time machine. We’re headed to the year 2000, when I was a new recruiter. I led a small team, and my boss told me I had to let go of one of my teammates. We were officially having layoffs across the board.

Shrinking Sales Teams

Every group had to make cuts, and no matter how hard I tried negotiating, I couldn’t spare anyone on my team. I was in my twenties and never imagined I’d be firing someone, but I had zero choice in the matter. After the news sunk in, I decided to call my dad.

If you’re wondering, I don’t normally call my dad in the middle of the day on a Wednesday, but I was stressed and couldn’t leave my desk. We had an open bullpen, so I dialed his number as discreetly as I could. 

I wasn’t expecting him to answer. And if you think this sounds like the “boiler room,” you may not be wrong.

My dad picked up. “Dad,” I whispered. “I’m at the office, and they want me to fire someone!”

In my mind, I’d imagined he’d be surprised and fairly upset, and maybe ask if I was working for an unscrupulous company. My dad only really wanted to know why I was whispering. But after I repeated myself, he heard what I was saying and gave me some judicious advice. I’ll share it in a minute.

First, let me be clear that letting people go stinks for all parties involved. Although saying so is about as insightful as proclaiming Avatar and Titanic were money-makers. It’s unnecessary to exaggerate well-known truths.

And if you’ve watched your colleagues exit stage left, you feel sad at first, and then once the sadness dissipates, relief washes over you. That relief breeds guilt, because you’re happy. Yes, it’s true. 

You’re happy because you still have a job, you’re one of the “lucky” ones, and your regular paycheck will hit the bank as planned. 

After all, you have mountains of inflationary bills to pay, and every time you go to the grocery store, you wonder how seventy-five dollars of groceries fits into one or two bags. Maybe you think fondly about that savings account you’ve been meaning to pay more attention to.

Salespeople Move In and Move Out

But eventually, you start to wonder if you should continue with your current employer or if finding shelter elsewhere is the prudent thing to do. Are the rocky times worth seeing through?

This reminds me of an old Brian Tracy adage:

• One third of people are entering the sales profession right now
• One third are staying put
• One third are on the way out, exploring other lines of work

Although it helps to be good at basic math in sales, becoming a sales professional is not like becoming an accountant. The accountant has a lot of job stability, and rarely stares down the idea of being fired for poor performance. 

The salesperson, on the other hand, need not wait for an annual performance review.

And recently, if you’re in tech sales, you know layoffs have been felt across sales and marketing teams throughout the sector. 

So if you’ve found yourself out of a job, hitting a wall, worried about making quota, or watching colleagues get laid off, this is NOT as abnormal as it may feel. It’s the winter season of the business cycle.

How bad will the winter be? The experts all around us seem to know, but the truth is, no one really does. 

But if job security is one of your key values, tech might be a difficult industry to work in, primarily because tech was created out of disruption, and most disruption is out of your control: mergers, acquisitions, new investors, new leadership, new ideas, new CEOs.

Minimizing Risk Through Deliberate Decisions

There are ways to mitigate the risks, though. Here are some simple ones, from easier to more difficult:

• Believing in what you’re doing
• Saving more of your commissions
• Making a regular effort to be a contributing team member
• Proactively building your network outside your current employer
• Being good, if not excellent, at your job
• Working with experienced leaders who have won in the past

Finding stability in other areas of your life may help balance things out. 

But if it’s still too much, it could be time to explore other industries. Instead of waiting for a unicorn opportunity to come along, now is a good time to get busy, reinvent yourself if necessary, and evaluate your options strategically.

When You Know, You Know

If you know tech sales is for you, then bravely weather this storm. And now I’ll share what my dad shared with me.

He said, “This is not the first downturn, nor the worst, and it will certainly not be the last. Today’s terrible storm will look like a rainbow five years from now. 

And in the moment, we don’t always agree with what life has in store for us, which causes us great frustration, because life’s circumstances are not meeting our current expectations. But you have to move forward, and you must believe things will work out.”

And you know what? He was right. Things work out, but they don’t always follow our timeframes or plans.

When I started my recruiting journey more than twenty years ago, it was at the tail end of a tech boom, on the cusp of a market bust. In the beginning, I’d go to get-togethers after work in San Francisco, and everyone in the city (myself included) seemed to be a recruiter of one type or another. 

Then, in 2001, the booming dot-com era ended, and layoffs ensued.

As a result, getting someone to work in tech after the bubble burst became difficult. Tech companies had to fight lackluster reputations for years, and people were much less interested in working for tech than they are today.

But tech companies went to work doing what they do best: building things. They built their teams, rebuilt their reputations, and played the long game. 

They revamped their image into a place people wanted to be, began offering perks like free food, and, unlike many other industries, they rarely fired ANY salesperson they hired for at least one year.

That gave every new sales hire time to learn the products, build pipeline, and close business, and if things didn’t work out after a year, it would be difficult for the salesperson to feel surprised. 

The strategy worked. Eventually, tech companies transformed their reputations into what we know today: cool, fun, exciting modern tech companies funded by sharp investors.

Remembering the Past

As for those recruiters in 2000, most were relatively new to the business and subsequently laid off. 

Many didn’t get back into recruiting, because when the bubble burst, recruiting roles were in short supply, so most newly minted recruiters migrated into other professions. Some smart ones even moved into tech sales!

So if you find yourself a bit doomsdayish on the space, remember what goes up comes down. Downturns happen, and so do booms. 

And I can assure you, the tech apocalypse is not here. Not yet, at least. Technology is still our future, and the sun will shine again on tech.

It’s perfectly normal for people to move in and out of different functions and businesses based on the times, preferences, and market circumstances. 

If you want to, you can too. If you’ve already been caught in a layoff, here are eight ways back from losing a sales job. Or you can mitigate your known risks and weather the current and future storms.

After all, this is the only business I know of that regularly manufactures unicorns. Plus, unicorns look good with rainbows!