Matt Dale: Say yes, raise your hand, and learn to speak CFO

"I still don't know what I want to be when I grow up, and I think that's okay. But I do know that whenever I said yes and did the thing well, it led to the next opportunity."

Author

Mercer Smith
September 25, 2025

Welcome to Escalations, a series where I’ll be sharing stories of some amazing careers that started in Customer Support. While many of these will be compiled into a book, I will also be regularly sharing stories here, too. If you like this content, please consider subscribing or sharing. 

Introduction: the starting point

Matt Dale’s career began the way many support careers do: helping people. In high school, he earned $5 an hour helping his graphic designer mom’s friends install Adobe InDesign on their computers, and by college he was running after-school internet skills classes for senior citizens and kids. But even as he built a knack for tech troubleshooting and human-centered problem solving, he still wasn’t sure where his path would lead.

After trying his hand at operations in a law firm merger (which ended with the two founding partners suing each other), he re-entered the tech world, this time in SaaS edtech. That accidental entry point launched a decade-long career leading and scaling support teams, navigating nine acquisitions, and helping guide a PE-backed company through sale.

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"What a perfect role: to be somewhere where you can help people and solve problems."

The growth path

What’s most striking about Matt’s journey isn’t a single title jump or flashy pivot. It’s the way he kept stepping up, quietly and competently, every time there was an opportunity. Whether managing a phone system migration, leading a physical office build-out, or integrating teams across continents, Matt was the person others could count on.

He also understood something early that many support pros learn later: leadership isn’t just about having the answers. It’s about being willing to step in and take ownership even when the task isn’t glamorous or clearly defined.

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"I had opportunities to do things, and I did them well. So company leadership looked at my results and said: this person is doing things well. Let’s give them more opportunities."

Implementing this in your own career

  • Look for pain points no one wants to own—and offer to take them on

  • Develop cross-functional curiosity, not just support depth

  • Cultivate trust before a crisis hits

  • Remember: visibility isn't bragging—it's advocacy

Breaking through: lessons & key decisions

1. Manage up by solving your boss’s pain

If you want to grow, figure out what your boss is worried about—and fix it. Matt credits much of his advancement to understanding what mattered to his leaders, then showing how he could deliver on it.

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"Everyone has a boss. And your job is to figure out how to take away your boss’s pain."

How you can apply it

  • Use 1:1s to ask what matters most to your manager

  • Track how your work contributes to their goals

  • Deliver context, not just numbers, when sharing updates

2. Say yes—even when it’s not in your job description

From handling real estate negotiations to conducting sales tax audits, Matt took on tasks far outside the traditional support remit. Why? Because someone needed to do it, and he was curious enough to figure it out.

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"There's a subset of people who say, 'That’s not in my job description.' And I always think, then how would I ever promote you?"

How you can apply it

  • Be the person who raises their hand, even for the weird stuff

  • Treat every project like a chance to learn and stretch

  • Say yes strategically, then follow through with excellence

3. Learn to speak CFO (and CEO)

Support teams often stay siloed from business metrics, but Matt believes the key to advancement is understanding the financials and aligning your work to them.

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"No one in a one-on-one has ever said to me, 'Can you help me understand how our team runs?' If someone did, I’d fall out of my chair—and then I’d invest in them."

How you can apply it

  • Ask your manager for visibility into financial reports

  • Take a free course on Excel or accounting basics

  • Practice turning support insights into business outcomes

4. Cultivate trust before you need it

When Matt led global team integrations and weathered delayed acquisitions, his ability to communicate transparently and consistently made all the difference. Trust wasn’t something he scrambled to build during a crisis—it was already there.

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"If they believe you’re aware of their needs, they can let go of some of the fear."

How you can apply it

  • Build regular cadences of communication

  • Be human—acknowledge uncertainty when it’s real

  • Invest in relationships before you’re in a transition

5. Know when to stay, when to move on

Matt spent over a decade at one company—longer than he now recommends for rapid career growth. But he learned when it was time to leave and how to use that time to reset. Now, as a consultant, he looks for alignment over titles.

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"I was there four years longer than I wanted to be. But I wouldn’t have known that if I hadn’t gone through it."

How you can apply it

  • Don’t let comfort keep you in a role that’s no longer growing

  • When stuck, ask: is this fixable or is it time to move?

  • Use transition time to reflect, reset, and refocus

Actionable takeaways

  • Cultivate curiosity. The people who move up aren’t just smart—they’re hungry to learn.

  • Know what your boss cares about. Then go solve it.

  • Be visible. Track your wins, share context, and advocate for your contributions.

  • Say yes—but say it with intention. It’s not about doing everything. It’s about doing the right things, well.

  • Lead with trust, not authority. Especially in hard times, people will follow someone they believe is looking out for them.

  • Recognize your support superpowers. Troubleshooting, context-switching, rapid learning—those are gold in any field.

Where they are now & final words of advice

Today, Matt splits his time between leading CX at Clearly Filtered and consulting through his firm, Moxie CX. He’s less interested in titles and more focused on meaningful work, balance, and helping others grow.

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"Support is like a liberal arts degree. It gives you skills that can take you anywhere—but you have to be the one to turn those skills into something more. No one’s going to do it for you."