We caught up with the brilliant and insightful Alisa Cook a few weeks ago and have shared our conversation below.

Alisa, appreciate you joining us today. How did you scale up? What were the strategies, tactics, meaningful moments, twists/turns, obstacles, mistakes along the way? The world needs to hear more realistic, actionable stories about this critical part of the business building journey. Tell us your scaling up story – bring us along so we can understand what it was like making the decisions you had, implementing the strategies/tactics etc.

People love to glamorize success stories, but the truth is, mine was built on trial, error, and a fair amount of chaos. There’s nothing “overnight” about it.

When I first started, we were doing great work for incredible clients. The problem was, they were what I call “whales”. massive, high-touch clients that took everything we had to serve. We were successful on paper, but scaling felt impossible. One more big client would have broken the system.

That’s when I hired a business coach who worked exclusively with digital agencies ready to grow the right way. The first thing I learned? I had to stop grinding and start leading. My biggest shift wasn’t in strategy, it was in mindset. I went from being buried in daily chaos to intentionally plotting my days like the CEO my business actually needed.

That meant trusting my team, even when it was uncomfortable. It meant stepping back from the details that kept me busy and focusing on the systems that would set us free.

We launched our first pilot program before everything was “perfect.” Honestly, it was messy. We made mistakes. We missed things. We heard feedback that stung a little. But we learned more in that process than we ever could have waiting for perfection. And the truth is, we’re still learning.

I’ve always said marketers have to market. We can’t preach strategy and systems to clients while hiding behind our own uncertainty. So I made myself the guinea pig. I ran the same kind of outreach and authority-building systems we build for clients, and that real-world experience gave us the clarity and confidence we needed to improve everything we deliver.

Inside the company, everything evolved too. Our team meetings used to be all about checking boxes. Now, they’re about vision, systems, and strategy. We’re focused on building the future instead of just surviving the week.

There have been hard hits along the way. Losing two clients in one week not long ago felt like getting punched in the gut. The old version of me would have panicked and started taking any client that came my way just to make up the gap. But that’s not leadership. Instead, I doubled down on improving the client experience, refining our processes, and investing in our own marketing.

Now, we only take on clients who value what we do, trust our process, and want a partnership. If we don’t deliver on our promise, we fix it. Sometimes that means discounted work, sometimes free. Because integrity matters more than image.

And every new offer we roll out starts as a pilot. Always. I can’t imagine doing it any other way now.

For years, I used to joke that I was “always on vacation, but never on vacation.” I’d take calls at 10 p.m. in Barcelona just to keep the business running. But this year, I took a five-week road trip across the Western U.S., visited 13 national parks, and actually lived my life; without everything falling apart.

That’s the result of scaling with intention. No shortcuts. No hustle-culture nonsense. Just clarity, systems, and a team that knows how to win together.

Bruised but lucky, and ready to grow more.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

Before I ever ran a marketing agency, I ran schools and educational organizations. I was an elementary school principal, a tutoring company owner, and a high school principal, and for more than two decades, I lived in a world where success depended on systems, communication, and people. You can’t lead hundreds of kids, teachers, and parents without learning how to balance chaos, structure, and empathy…all at once.

That experience shaped everything about how I lead today. Education is at its core about helping people see what’s possible, giving them the tools to get there, and holding them accountable to their own potential. That’s exactly how I see my work now.

At Ally Marketing Systems, we help B2B coaches, consultants, and service providers stop living on the referral rollercoaster and start building predictable lead systems that actually work. We specialize in LinkedIn authority and cold email systems; both built to sound human, not robotic.

Our clients usually come to us frustrated. They’ve tried every “marketing hack” or burned money on agencies that promised results but delivered noise. Their biggest pain points are always the same: inconsistent leads, overwhelming options, and no clear path forward. What sets us apart is that we don’t sell hype. We build systems. Smart, human-first systems that create structure, consistency, and confidence in their client acquisition process.

And here’s where my education background comes full circle. I see my role as part strategist, part teacher, and part coach. I don’t just want our clients to get results; I want them to understand how it all works, so they can lead their businesses with clarity. When I teach them how to build systems that work while they sleep, it’s the same satisfaction I used to get when a student suddenly “got it.”

I’m most proud of how far we’ve come by staying authentic and refusing to play the “bro marketing” game. We’ve built an agency that thrives on relationships, not gimmicks. Our approach is personal, transparent, and rooted in genuine collaboration.

At the end of the day, what I want potential clients to know is this: we’re not here to sell you fluff. We’re here to help you build something sustainable. Something that reflects you. And something that gives you the freedom to stop hustling 24/7 and start enjoying the business, and life, you’ve worked so hard to create.

How’d you build such a strong reputation within your market?

What’s helped me build my reputation in this industry is that I tell the truth, even when it’s not flattering, and especially when it’s not trendy.

There’s a lot of noise out there in marketing. Too many “experts” are chasing the next shiny tool or formula, and not enough people are building systems that actually work for humans. I built my reputation by staying focused on substance over flash.

From the beginning, I’ve been transparent about what works, what doesn’t, and how much testing, failure, and learning it actually takes to build something predictable. Clients respect that. They know I’m not going to sell them a quick fix or a one-size-fits-all funnel. I’m going to help them build something sustainable that they can trust.

I also think my education background played a big role in how I show up. Being a former principal taught me how to listen deeply, meet people where they are, and teach in a way that empowers, not intimidates. That approach built trust. And trust, over time, is what builds a reputation.

My clients know I’m hands-on, I’m human-first, and I care about their success like it’s my own. I don’t hide behind buzzwords or pretend that marketing is easy. I stay in the trenches with them, learning, refining, and improving every single day.

That’s what built my reputation. Not perfection; consistency, honesty, and a genuine desire to help people grow.

Have any books or other resources had a big impact on you?

Absolutely. I’m a firm believer that great leaders never stop learning, and the right book at the right time can completely shift how you think about business and life.

1. Buy Back Your Time by Dan Martell
This book was a game changer for me. Martell’s concept of building systems and teams that let you focus on high-value work hit home. As a recovering “do it all myself” entrepreneur, learning to delegate and design my business around freedom, not just revenue, changed everything.

2. Radical Candor by Kim Scott
As a former principal turned agency owner, this one resonated deeply. Scott’s philosophy of “caring personally while challenging directly” mirrors how I try to lead my team. It’s about honest feedback, mutual respect, and building a culture where people can grow without fear.

3. Dare to Lead by Brené Brown
This book helped me reframe what strong leadership looks like. Vulnerability isn’t weakness. it’s the foundation of trust. Especially as a female founder, embracing that has been powerful. Brown’s work reminds me that being real, not perfect, is what builds connection and credibility.

4. Company of One by Paul Jarvis
This one speaks directly to my belief that “bigger” isn’t always “better.” Jarvis challenges the obsession with endless scaling and reminds entrepreneurs that building smarter, leaner, and more intentionally often leads to more fulfillment, and profit.

Each of these books reinforced a key truth I live by: success isn’t about working harder, it’s about working with clarity. Build systems. Lead with honesty. And always keep the human element front and center.

Contact Info:

• Website: https://allymarketingsystems.com
• Linkedin: https://LinkedIn.com/in/alisacook