Smart Agency Masterclass with Jason Swenk: Podcast for Digital Marketing Agencies

Why Traditional Team Structures Are Failing Modern Agencies


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Are you still running your agency like it’s 2010?

You know the setup: rigid roles, top-down management, a “just get it done” culture.

If that sounds like your agency, chances are you’re the bottleneck. You’re stuck in the weeds, making every single decision, dealing with high churn, and wondering why output is low despite how hard everyone’s working.

This is the story for most agency owners at the 7-figure stage. But the agencies scaling fastest today have evolved—and we’re breaking down exactly how.

Why Most Agencies Get Stuck

Most agency owners didn’t plan to be CEOs. You were good at strategy, sales, design, or delivery. Then suddenly—boom—you’re the boss. Now the team looks to you for every decision, every review, every answer.

The problem isn’t your team. It’s the lack of vision. When there’s no clear direction, your team can’t lead themselves—because they don’t know where the hell they’re going.

Once I clearly communicated the mission—“We’re building the resource I wish I had”—everything changed. Decisions got made without me. Accountability rose. That’s what happens when people lead toward a clear goal.

Key shift: You don’t need more doers. You need more leaders.

Attracting A-Players (Not Babysitting B-Teamers)

A-players cost more—about 20% more on paper—but they produce 10–20x more than your average B-level staffer. They don’t need to be told. They take ownership.

So how do you attract them?

Build a brand people want to belong to. Ramblin Jackson, one of our mastermind members, calls their team “Ramblers.” It’s fun. It creates identity. It’s not just a job—it’s a tribe.

Make your job posts feel like sales letters. “Here’s who we are. Here’s why it matters. Here’s what you’ll help us build.” Ramblin even walks candidates through the hiring process on their site to build trust.

Put your team on display. Show them off on your website, on social, in your wins. A-players don’t just want just a job, they want purpose. Make it visible.

Building a High-Performing Culture

Great teams don’t happen by accident. They’re built on clarity, feedback, and connection.

Here’s how to build a culture that scales:

  • Communicate Clearly. Use Looms instead of emails. Weekly standups. Show people what winning looks like—and support them to get there.

  • Give & Receive Feedback. Quarterly ask: What should we start, stop, and continue doing? Then actually do something with those answers.

  • Support Growth Paths. Not everyone wants to lead. Some want to be elite specialists. Either path is valuable—support both.

  • Forge Connections on Purpose. Especially if you’re remote. Retreats, local meetups, even casual Zooms help remind your team: we’re building something together.

  • Stop Managing. Start Coaching. Reviews are fine. But coaching is where the magic happens.

Ask your team:

“Where do you want to grow?”

“What ideas do you have to help the company grow?”

You’re not just managing performance—you’re investing in potential.

Then teach them the 131 Method to make better decisions without you:

  • 1 What’s the issue?

  • 3 What are 3 possible solutions?

  • 1 What’s your one recommendation?

This trains your team to think like owners.

Also: stop assigning tasks—start assigning outcomes. Let them figure out the how. Debrief when things go sideways, but stop micromanaging. Growth comes from ownership.

Sustainability Is the Long Game

You can’t grow a team if they’re burned out, checked out, or walking out.

Here’s how to protect your team’s energy:

  1. Cut the fluff meetings

  2. Encourage real time off

  3. Create space for recovery (mental health days, no-meeting weeks)

  4. Celebrate wins publicly (Slack shoutouts, weekly recaps)

  5. Keep people connected—virtually and IRL

Culture isn’t perks. It’s how people feel when they’re building with you.

 The traditional agency model is broken. You don’t need more hands—you need more heads.

Build a team of leaders.

Create a culture of clarity, connection, and coaching.

Get out of the damn way—and let them fly.

If you’re ready to attract better clients and become uncuttable, check out the Attract Masterclass. It will help you position your agency to pull in the right leads instead of just more leads.

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Smart Agency Masterclass with Jason Swenk: Podcast for Digital Marketing AgenciesBy Jason Swenk

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