When crisis becomes opportunity: A chat with Alex Olley

When crisis becomes opportunity: A chat with Alex Olley

Written by
Morgan J. Ingram
Updated on
November 25, 2024
Reading time
6 min.

2023 was brutal for tech companies.

Headlines screamed about layoffs.

Sales teams got cut in half.

Quotas doubled.

Marketing budgets vanished overnight.

I've talked to hundreds of sales leaders dealing with the fallout. Most tell the same story – missed targets, burnt-out teams, and pipelines drying up.

That's why this conversation stopped me in my tracks.

"2023 was the best year of my career," he said with a big smile. "But it was also the hardest."

When I hopped on Riverside with Alex Olley, CRO at Reachdesk, I knew this chat would be different. You could feel his energy through the screen.

While most tech leaders were still recovering from 2023's punches, Alex was ready to share how he turned crisis into gold.

The money side that nobody talks about

Alex did something that shocked me. He totally flipped how he handles quotas. I've talked to hundreds of sales leaders, but this was new.

"Everyone talks about motivation and sales tactics," he told me, leaning into the camera. "But nobody wants to dig into the real economics of how we set up our teams for success."

Most leaders just throw numbers at their team and hope for the best. Alex went deeper.

He looked at:

The result? His team crushed it with 94% of the goals hit. That's not just good – that's remarkable in this market.

"Want to know the real secret?" he asked. "It's not about pushing people harder. It's about understanding the money in your business and paying people what makes sense."

Breaking down walls (literally)

Here's where things got interesting. Alex showed me his weekly GTM Ops meetings. But these weren't your usual boring check-ins.

It had Marketing, Sales, Partnerships, and Ops all in one room. No finger-pointing. No "that's not my job." Everyone owns the number together.

This wasn't just talk. They were actually doing it.

He shared how most companies mess this up. Marketing blames Sales for not working leads. Sales blames Marketing for bad leads. Ops is stuck in the middle. But at Reachdesk? They created one team with one goal: revenue.

When you have one goal, it's easier to work together as a team.

Numbers that actually matter

Halfway through our chat, Alex dropped another truth bomb.

He only tracks two things:

That's it. No complicated dashboards. No vanity metrics. Just the stuff that shows if money's coming in or not.

"Look at this," he said, sharing his screen. "It's not about tracking everything. It's about understanding the story behind the numbers that matter."

He showed me his simple dashboard. While other companies drown in data, his team knows exactly what moves the needle.

The secret weapon: getting help

Now, here's what really hit home for me. Alex didn't try to be a hero and figure everything out alone.

He joined communities like Pavilion. He had coffee chats with other sales leaders. He wasn't afraid to say "I don't know" and ask for help.

"You know what the biggest mistake sales leaders make is?" he asked. "Thinking they have to figure everything out alone."

This is huge. In sales, we often think we need to have all the answers. It's okay to admit that you don't know something and seek the help you need.

Alex showed that the real strength is knowing when to learn from others.

How to make this work in your company

What I love about Alex's approach is how actionable it is.

Here's the step-by-step plan he laid out:

"First 30 days":

"60-90 days":

"By 6 months":

Common traps to watch for

Before wrapping up, Alex shared the three biggest traps he sees leaders fall into when trying to turn things around:

"First, they rush to fix everything at once," he said, shaking his head. "You've got comp plans, tech stack, pipeline issues, team structure – it's overwhelming. Pick one thing. Master it. Then move on."

"Second trap? Not sharing the 'why' behind changes," Alex continued. "Your team isn't dumb. They know when things aren't working. But they need to understand where you're going and how you'll get there together."

This hit home. The best changes I've seen always start with clear communication.

"The last trap is the killer – giving up too soon," Alex leaned back in his chair. "Real change takes time. Six months minimum. Usually, it's closer to a year. But most leaders panic after six weeks if they don't see results."

He shared how his own transformation took eight months before the numbers really showed it was working. "But when it clicked," he smiled, "everything changed at once."

Why this matters for you

Looking back at our chat, I realized why Alex's story hits differently.

He didn't just survive a tough year – he used it to completely change how his team works.

Here are the big takeaways:

He showed us that our biggest challenges might actually be our biggest chances to grow. But only if we're willing to throw out the old playbook and write a new one.

For me, this is what transformation looks like. Not fancy strategies or complex systems. It's about taking a step back to have clear thinking, smart changes, and the courage to do things differently.

For all my sales leaders out there: Take a page from Alex's book. Look at your numbers differently. Bring your teams together. And most importantly, don't be afraid to build something new.

Sometimes, the hardest years really can become your best if you're brave enough to change how you work.

Want to hear more details from my chat with Alex? Check out the full episode of On the Record!

About the author
Morgan J. Ingram
Morgan J. Ingram is a dynamic sales coach, keynote speaker, and host of On the Record, a podcast about the real challenges of sales leadership. With a passion for empowering sales teams, Morgan specializes in actionable strategies and authentic conversations that inspire growth. Known for his high energy and relatable insights, he’s a trusted voice in the sales world.