Navigating Agency Growth and Leadership

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Ever wonder what separates a $1M agency from a $30M agency? It’s not just better SEO or more employees. It’s how you run the business behind the scenes. We sat down with today’s featured guest to dig into what’s powered his insane growth from barely crossing seven figures back when we first met… to now staring down $35–$40 million in pure service revenue. He’s sharing some great advice on the evolution of his role as CEO, his new-found love for podcasting, and all kinds of golden nuggets for agency currently in the “no man’s land”.

Chris Dreyer is the CEO of Rankings.io, a law firm marketing services agency that delivers exceptional results for attorneys without compromising on customer service. He’ll discuss his agency's substantial growth from under a million to over $30 million in revenue, his reliance on data and key performance indicators (KPIs), the transformative role of AI in various aspects of his operations, the importance of in-person client meetings for building relationships, and much more.

If you’re still guessing your numbers or putting off tracking your team’s time — you’ll want to pay attention.

In this episode, we’ll discuss:

• The CEO’s true job.

• Hidden agency growing pains.

• The key to client happiness.

• In-person hustle and outbound sales.

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Sponsors and Resources

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Why Data Became Like a Religion

Back when Chris and I first locked ourselves in a tiny Atlanta room for a workshop, Rankings.io was barely peeking over the $1M mark. He was still deciding who to serve and how. Fast forward about 8-9 years to today, and he says there’s no bigger reason for his success than his top-to-bottom data obsession.

Most agency owners track just enough to feel busy: a few pipeline numbers, maybe close rates if they’re fancy. But Chris tracks everything.

He knows the lifetime value of a client paying $5K a month versus $10K a month. He knows exactly how each account manager’s retention rate impacts revenue. He even scores sales reps like a fantasy football league.

And it’s not just vanity metrics. If an account manager is great at keeping clients but terrible at preserving the original retainer size, they fix it. If time tracking shows poor utilization? They fix it. It’s relentless.

The big unlock for him was getting a real CFO to build this machine — and shifting from QuickBooks to more robust systems like Sage. No more flying blind or hoping for the best. If you don’t know your LTV, churn, win rates, and retention by the exact dollar, you’re leaving growth up to luck.

How AI Became His Secret Weapon (and Why You Should Care)

Most agency owners dabble in AI: a blog here, a few prompts there. Chris has gone full cyborg.

Every single month, his team uploads their entire reporting package into ChatGPT. They don’t just glance at dashboards — they get an AI board of advisors that points out trends, flags issues, and even suggests campaigns based on sales funnel leaks.

If they have clients applying but not booking, the AI says: launch a re-engagement sequence. If they’re not sure why the expense spike looks off, the AI will cross-check it with your event calendar. Chris used to hate looking at financials — now AI does the heavy lifting.

When it comes to AI agents, they’re not doing as much and prefer to use AI assistants for content, link building, and optimization. He even has an AI board of advisers with different personalities.

This isn’t replacing people. It’s leveling them up. It’s like strapping a rocket to every role — so you can do more without burning out your team.

If you’re not leaning on AI for context and next steps, you’re probably making slower (and worse) decisions than your competitors.

The CEO’s True Job: Gotta Catch ‘em All

Now that he’s running an agency pushing $40M in service revenue (not pass-through, real revenue) Chris defines his role as: “Playing people Pokemon. Gotta catch ‘em all. I get the clients, and my president keeps them.”

He sets the vision, runs point on marketing and sales, hosts the podcast, and stays the face of Rankings.io. Meanwhile, his right-hand man, Stephen, owns retention and delivery. This split lets Chris hunt big opportunities without getting bogged down in fulfillment fires.

It’s the perfect example of how an owner’s role must evolve. If you’re still stuck in the weeds, wearing every hat, and calling that “leadership” — you’re capping your agency’s growth.

The goal isn’t to do everything. It’s to build a team that does everything better than you ever could alone. And Chris’s story is living proof.

The Hidden Growing Pains Nobody Warns You About

Ever heard of the dreaded “no man’s land” for agencies? For Chris, it began after he crossed the $8M to $10M mark and things got painfully awkward fast.

In this stage, you’re forced to hire the roles that don’t directly bring in revenue: HR, finance, middle managers. Suddenly, your once-scrappy margins start leaking everywhere. It feels counterintuitive, all these new salaries, and yet no extra billables. But here’s the catch: this is the awkward but necessary step that’ll set you up with the infrastructure to move from $10M to $15M, $20M or beyond.

This is generally the zone where you feel like an imposter CEO — one foot in the hustle, one foot in the corporate world you swore you’d never build. The truth is, every growing agency owner faces this inflection point. And if you get it right, you build a structure that can handle scale. If you get it wrong, you risk staying stuck at the same revenue ceiling year after year.

You Can’t Turn It Off — And Maybe That’s Okay

Most founders agree they find it difficult to turn their business brain off, and honestly, they don’t want to. Business is the hobby. While their kids are at soccer practice, their brain is rewriting the service agreement or tweaking a proposal.

Sure, there’s a cost. Vacations come with podcast episodes in the car. Weekends sometimes mean scanning P&L spreadsheets. But, as Jason and Chris admit: the key to staying sane isn’t to “balance it perfectly” — it’s to have the right partner who gets the obsession.

Because when you’re building a business that supports dozens, even hundreds of families, switching it off just isn’t realistic. So you find the support system that lets you go all in and come home for dinner.

Why Core Values Actually Matter

Early on, you might roll your eyes at “company core values.” Chris admits he did and saw it as just a lot of fluff. But once you’re managing 50, 100, or more people, vague values don’t cut it — you need a shared language to protect the culture.

His agency now runs on three non-negotiables:

• Excellence (do great work, always)

• Execution (don’t just talk, get it done)

• Grit (stick with hard things for the long haul)

While he used to rely on platitudes like “team player” — he sees now that the wrong person will be weeded out fast as long as the core values are clear. He also bails at the mention of “work-life balance” in an interview. Because for this team, the culture is built for people who like working hard.

The Surprising Key to Client Happiness

Think your killer case studies will keep clients happy forever? Think again. Client happiness is very subjective and your biggest churn risk isn’t bad work — it’s bad relationships.

Sure, you can track Net Promoter Scores all day. But real retention comes from catching early warning signs, which Chris calls “saves”. A client going quiet, missing calls, or hinting they’re not vibing with an account manager should be signs to take action, if you start tracking them, as he has.

And here’s the overlooked move more agencies need to revive: visit your clients in person. Everyone’s got Zoom fatigue. Booking a flight and breaking bread goes a long way toward making you not just a vendor, but a trusted partner.

How In-Person Hustle and Outbound Hunting Keep You on Top

Even with all the fancy dashboards, AI copilots, and mega forecasting tools, Chris and his president still jump on planes to shake hands with clients. They even budget for it.

When you’re running a high-ticket service where each client can be worth $125,000 or more over their lifetime, dropping a couple grand to show up in person is a no-brainer. It’s how you show you care more than the next guy who’s sending templated emails and hiding behind Slack.

Chris’s take is simple: Want to stand out? Do what you say you’re going to do. Show up. Make your clients look like heroes. When a big-name CEO flies out to see you — even if you didn’t sell them the deal — you remember that. Big relationships should get the handshake treatment.

Using AI for Confidence in an Agency Acquisition

Chris didn’t buy another agency until he was already pushing $30 million, while most owners pull that trigger way earlier to leapfrog plateaus.

Why wait? According to Chris, he didn’t have the confidence to do it. Until AI changed that.

He used ChatGPT to run diligence questions, draft the LOI, check for financial holes, and sanity-check the entire earnout structure. Sure, he has a great CFO — but that AI second brain made the whole thing faster and way less intimidating.

Now that he’s got the first deal under his belt, he’s hungry for more. That’s how scale works: get clarity, take the shot, rinse and repeat.

Pro tip: If you’re scared to buy, partner, or hire, dump your numbers into AI. Ask it what it would worry about if it were buying you. It’ll show you every skeleton in the closet — so you can fix them now.

Why Outbound Sales is Your Insurance Policy

Chris used to be very resistant to doing outbound but now it is saving him from the Google rollercoaster.

Inbound is sexy when it works. But we all know it can be feast or famine. Algorithms change. Referrals dry up. And you’re stuck hoping this month’s pipeline looks like last month’s.

After getting tired of hoping, Chris built an outbound team that’s now about 30 people deep. He’s got BDRs making 50 high-quality calls a day, sending out handwritten notes with books, running multi-channel outreach, and gifting prospects to cut through the noise.

Each practice area has its own sales enablement rep feeding lists, building sequences, and arming the closers with context. It’s consistent and it means Rankings.io can hunt, not just fish.

Big lesson: if you don’t control at least three lead sources (inbound, outbound, and strategic partners), your agency’s growth is on borrowed time. Don’t put all your eggs in Google’s basket. Outbound is insurance.

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