Have you ever been knee-deep in running your business, feeling like everything is just…chaos? Like you’re fighting fires, closing deals, but somehow, it all feels like it’s going to collapse if you don’t stay on top of every single thing? That’s exactly the feeling Jacki Leahy, founder of Activate the Magic, described when she shared her entrepreneurial journey with me.

Jacki’s path is fascinating because it’s not the typical “I started a business and everything fell into place” story. No, it’s a grind—it’s messy, but she found a way to make it work. What stuck with me during our conversation was how she managed to wrangle the chaos of running a business into something sustainable. It wasn’t about hitting sales quotas or managing data; it was about building systems that make everything flow.

Let’s break down two key lessons from my conversation with Jacki that can help anyone struggling to scale their business.

Revenue Operations: The Secret to Organized Growth

When Jacki started talking about RevOps (Revenue Operations), she had this analogy that really hit home. She said RevOps is like “the plumbing and HVAC of a company’s go-to-market strategy.” I don’t know about you, but that makes total sense. You don’t see the pipes and vents in a building, but if they’re not working, everything falls apart.

RevOps is about connecting the dots between sales, marketing, and customer success. But it’s not just some fancy term. Jacki found her passion for this while working at tech startups, where she realized the magic wasn’t just in making the sale—it was in building the right system behind it. She said, “I could create pipeline by myself, sure, but the real value came when we weaponized a friendly group of awesome people.”

The way she explained it, RevOps is more than just data or automation—it’s about creating processes that allow your team to thrive without you having to micromanage every step.

Key Takeaways from Our Discussion:

  • If your sales, marketing, and customer success teams aren’t aligned, you’re leaving money on the table.
  • Systems are everything. If your data isn’t organized, you’re guessing.
  • Sustainable growth comes from processes that outlive your daily involvement.

Scaling Beyond Founder-Led Sales

Every entrepreneur I know has hit that moment where they realize they can’t do it all. You’re the one closing deals, keeping the lights on, but at some point, it’s just not sustainable. Jacki had the same experience, and she laid it out in a way that I think a lot of us can relate to. “It sounds like a great problem when deals are coming in fast, but it’s also terrifying when you don’t know how to manage them.”

That’s where RevOps comes in—right at that tipping point when you need to go from founder-led sales to a scalable operation. Jacki’s firm helps businesses make that leap. She explained that businesses often hit a wall when they can’t figure out how to handle growth. At that point, you need systems, not just hustle.

She put it plainly, “When you’re at the point where deals are coming in, and you don’t know how to serve them—that’s when RevOps steps in.” It’s that shift from being in every deal to having systems that manage the flow for you.

What I Learned from Her Experience:

  • Founder-led sales can only take you so far before you hit a wall.
  • You need clear systems to handle growth, or else you’re just putting out fires.
  • RevOps allows you to transition from hustle mode to organized growth mode.

Reflections from the Interview

As Jacki and I talked, I kept thinking about how so many entrepreneurs—myself included—spend way too long trying to do it all ourselves. It’s like we’re afraid to let go of the reins. But Jacki’s story is a great reminder that scaling a business means trusting your team and building systems that take over where you leave off.

She didn’t sugarcoat anything. Running a business is hard. Jacki shared the moments when she was worried about making payroll, questioning how she was going to keep everything together. But what stood out to me is that she kept pushing forward, not by working harder, but by working smarter.

She said something that really hit me: “I was fired from my dream job on a Tuesday, and by the next Monday, I had launched my company.” That’s resilience. That’s grit. And that’s what separates successful entrepreneurs from those who burn out.

Here’s What I’m Taking Away:

  • Resilience is non-negotiable. You’re going to hit setbacks; how you respond to them makes the difference.
  • Know your strengths and focus on them. Jacki knew her magic was in operations and systems—she doubled down on that.
  • Build systems early. If you’re constantly putting out fires, you’re doing it wrong.
  • Trust your team. You can’t scale if you don’t let other people take the wheel sometimes.
  • Success isn’t just about revenue—it’s about sustainable growth and managing the long game.

Final Thoughts

It’s easy to get caught up in the daily grind of entrepreneurship and lose sight of the bigger picture. But what I took away from my conversation with Jacki Leahy is that building a successful, scalable business comes down to creating systems that can run without you.

If you’re an entrepreneur feeling like you’re stuck in founder-led sales or like your business is one misstep away from falling apart, it might be time to take a step back and think about your systems. Are they built to scale? Are they sustainable? And most importantly, do they allow you to focus on what you do best?

There’s so much more to learn from Jacki’s story. Check out the full episode of Never Been Promoted to hear all about her journey: DON’T Overlook the Power of Data: Jacki Leahy’s Advice on RevOps

CONNECT WITH JACKI LEAHY:

LinkedIn: https://www.linkedin.cm/in/jackileahy/

Website: https://activatethemagic.com/croconsigliere