Jennifer's career path to CEO

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How are the new technologies and tools shaping the future of agencies? How can you create an agency that outlasts trends? When you've been around for 75 years in the ad world, you've seen it all, from Mad Men, media buying by fax, the rise of the internet, and now, AI. Today's featured guest runs an agency that has been doing full-service marketing since 1950. What's impressive isn't just their longevity but also how they've stayed relevant and human in a business that changes faster than a TikTok trend.

Jennifer Spire is the CEO of Preston Spire, an independent Minneapolis-based creative agency that's been helping brands grow with full-service marketing since 1950. She's the agency's fourth CEO, starting in small independent agencies, rising through global holding companies, and bringing both worlds' lessons to how she leads today. That mix of experiences shaped her leadership style grounded in independence, driven by creativity, and fiercely protective of agency culture.

In this episode, we'll discuss:

• Building a culture that lasts seven decades and beyond.

• Why independence still matters in the agency world.

• The future of agency talent and AI.

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How One Agency Has Stayed Relevant for 75 Years

Preston Spire started as a design shop in 1950 and quickly grew to a full service advertising agency, which differs from what we think of as full service today. Over the decades, it's evolved continuously, reinventing itself with every shift in marketing.

Jennifer says the real secret to their longevity is adaptability. "It's really hard to continue to evolve and stay strong, but I think there's a lot to be said for an agency that can evolve and still grow while being relevant."

Now they're 25 years away from a century, which is both impressive and humbling, as well as something they want to highlight more. Surprisingly, some advisors have actually told Jennifer it'd be best to not mention their 75-year run, since some might assume a 75-year-old agency should be bigger by now.

However, Jennifer has a different perspective. For her, you don't have to be one of the biggest agencies to be better and longevity isn't a weakness but rather proof of resilience and reinvention.

From Big Agency Bureaucracy to Small Agency Freedom

Before joining Press Inspire, Jennifer spent years inside the machine of large agencies, where shareholder-driven decisions often overshadowed what's best for clients or teams. There, she learned that you don't have to be bigger to be better, a philosophy that now fuels how she runs Press Inspire, as she has chosen to keep it small enough to stay personal but strong enough to compete with anyone.

Once she left the big-agency world for an independent shop, Jennifer cut her teeth doing everything from answering phones, assisting on shoots, starting media departments, and running PR. That early experience taught her the one skill every agency leader needs — resourcefulness — something she now encourages young people to develop early in their careers.

Her time at big agencies, though, showed her what not to do. "You end up making decisions that are best for shareholders, not clients," she said. "At a smaller agency, I wanted everyone to be able to chart their own path and make decisions that serve both the client and the team."

Building an Agency Culture Keeps People for Deacades

People stay for decades at Preston, some for 37 years, others 30, and three just recently celebrated 25-year anniversaries. That kind of loyalty is nearly unheard of in today's agency churn cycle.

So what's the secret? Balance. Jennifer encourages collaboration between long-time employees and newer hires with fresh perspectives. The agency operates in a hybrid setup, with three days in-office to keep creativity flowing while maintaining flexibility. It's a rhythm that keeps collaboration alive without burning people out. "Being together helps," she said. "That human connection is something you can't replicate over Zoom."

Their internal compass is guided by what they call COOP values: Courage, Originality, Openness, and Positivity. The team is encouraged to take risks, fail fast, learn, and keep moving forward.

Leading with Clarity: Building Alignment and Growth Paths

Jennifer may be CEO, but being at a smaller agency she's not above the grind. She manages operations, oversees HR and finance, and still maintains direct relationships with every major client. That visibility matters because, as she explains, clients need to know leadership is invested in their business.

Her team structure also breaks down roles by what percentage of their time is spent leading, managing, or making. This clarity helps people grow without being shoved into management if it's not something they want for their careers. This way, they get to build their unique path within the agency, a key to keeping them happy with their work.

Quarterly goals, regular feedback, and individualized growth paths keep everyone aligned and fulfilled — a framework that scales culture without micromanagement. Furthermore, constant feedback, quarterly goals, and individualized growth paths help keep everyone aligned and fulfilled.

Why Staying Independent Still Wins for Some Agencies

Does a 75-year-old independent agency get offers from the big holding companies? They do, actually; all the time. Jennifer says M&A emails land in her inbox daily. But she's not interested. "We've had serious talks with other agencies," she said, "but we've said no every time. Staying independent is critical to our success."

If they sold, they'd probably start making decisions for investors instead of their people and be back in the big agency world she escaped.

For Jennifer, independence isn't just about control, it's about protecting the culture that makes their agency different. The freedom to put clients and people first is what keeps the agency thriving.

Preparing for the Future: AI's Impact on Agency Talent

Jennifer's not blind to the future. She's already planning staffing and financial strategy through 2030, a move that would make most agencies sweat. One question she's wrestling with: how AI will change entry-level roles and career paths.

"AI has been an incredible tool and has allowed us to be more efficient," she said. "But if it takes away too much of the junior work, where do mid-level people come from five years from now?"

The truth is that the jobs won't vanish, they'll evolve. Junior people using AI can perform at mid-level. Mid-level people can perform like senior leaders. You'll just need fewer of them.

Still, Jennifer sees it as a call to action for colleagues and agency leaders alike: train people not just in the AI tools, but in critical thinking, problem solving, creativity, and the human side of marketing.

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