Welcome to Clarity Digital Pod. I’m Al Sefati, your host.
In this episode, I talk with Steve Gehlen, Director of Digital Marketing and E-commerce at Wilco Farm Stores. We dive into the big shifts shaping marketing leadership today — from post-COVID business changes and tighter budgets to the rise of AI and internal team challenges.
This isn’t just a tech conversation. It’s a real-world look at how digital leaders are adapting in one of the most complex times our industry has ever faced.
Post-COVID Digital Whiplash: How Marketing Teams Are Rebalancing
Steve opened by describing today’s landscape as a convergence of pressures — post-COVID team restructuring, economic uncertainty, and major privacy and platform changes. During the pandemic, many digital teams expanded rapidly. E-commerce surged, and marketing budgets grew. But as customer behavior returned to normal, companies started pulling back.
“We got an influx of budget and people during COVID—and then, suddenly, it was like, do we need all these people?” — Steve Gehlen
He also touched on how broader macroeconomic factors — like tariffs and inflation — are impacting business strategy and marketing operations. Even projects that were once greenlit are now paused or canceled entirely. It’s clear that digital leaders are operating in a more volatile, uncertain environment than ever before.
AI: Disruption or Acceleration?
While AI isn’t the only story here, it is a major one. Steve and I agree — AI isn’t here to replace marketers, but it is redefining how we work.
From simplifying ad structure to accelerating content production, AI is removing the grunt work so marketers can focus on higher-level creative and strategy. But it also brings new responsibilities. Marketers now need to understand how to prompt tools, vet platforms, and know when AI makes sense — and when it doesn’t.
“I’ve never been part of an in-house team that had enough people to take advantage of every digital channel. AI helps us do more, not necessarily do it with fewer people.” — Steve Gehlen
We both see AI as a multiplier — not a shortcut. And as costs inevitably rise and platform complexity grows, digital leaders will need to be more selective and strategic than ever.
What No One Talks About: Internal Politics and Organizational Friction
Some of the most important parts of our conversation weren’t about tools or channels — they were about people.
Steve and I discussed the internal friction that slows down even the most talented digital teams: territorial behavior, politics, and resistance from senior leaders. These challenges rarely make it into blog posts or vendor case studies — but they’re real.
“Internal leaders deal with things no one talks about — staffing, efficiency, politics, and territory battles. That’s the stuff under the surface that makes this job hard.” — Steve Gehlen
For me, this really hit home. I’ve experienced the same barriers, and in fact, it’s one reason I started my own agency. Sometimes, great digital work only happens when you remove the politics.
Digital Strategy Exchange: A Network for the Real Work
To address these challenges, Steve launched Digital Strategy Exchange, a peer network built exclusively for in-house digital leaders. No agencies. No vendors. Just brand-side professionals who understand the work — and the pressure — from the inside.
This isn’t Steve’s first time building something like this. Over 20 years ago, he founded the Internet Strategy Forum, which grew to 1,600+ members and had chapter leaders from Disney, IBM, Visa, and Intel. Now, he’s rebooting that model for 2025 — with a sharper focus on AI, platform fatigue, and leadership resilience.
“When I was meeting monthly with peers, my professional growth shot up. There’s no replacement for peer-to-peer learning in this space.” — Steve Gehlen
Digital Strategy Exchange is about creating that VIP-room experience you get at great conferences — where people actually share what’s working, what’s not, and how they’re navigating this evolving landscape.
What’s Next for AI and Digital Teams?
Toward the end of the conversation, we talked about the future — especially around AI tools, Agent AI, and platform bloat.
Steve sees the potential in Agent AI, but he’s cautious. Some tools have already overpromised and underdelivered. And many of today’s low-cost AI platforms are subsidized by investor funding. That won’t last forever. As costs rise, leaders will need to evaluate what’s essential versus what’s hype.
“You see all the headlines, but a lot of it doesn’t deliver on the hype. I’ve seen companies pilot AI tools and pull them back because they just didn’t work in reality.” — Steve Gehlen
It’s not about replacing marketers — it’s about empowering teams to do more with what they have. But those marketers have to evolve. They need to learn how AI works, how to use it effectively, and how to evaluate when it truly adds value.
“Your job might not be replaced by AI — but it could be replaced by someone who knows how to use it.” — Steve Gehlen
From Nike to Nonprofit: Steve’s Career Path
Before his current role at Wilco, Steve helped launch Nike’s first website in the early days of the internet. His background in both film and computer science gave him a rare mix of creative and technical thinking — the exact blend that modern marketers need today.
He’s also founded nonprofits, produced events, and run conferences for the creative economy. One of his organizations, Keeping the Arts, provides grants to arts teachers across Oregon.
“You have to be slightly crazy to produce events for fun — but I enjoy it. It’s part of who I am.” — Steve Gehlen
His passion for storytelling, creativity, and building community still drives his work today.
Final Thoughts: What It Really Takes to Lead Digital Marketing Teams in 2025
This episode wasn’t just about AI, or COVID, or any single trend. It was about what it really takes to lead a digital marketing team in 2025: clarity, adaptability, and a strong peer network.
Whether you’re navigating shrinking budgets, learning AI tools, or dealing with internal politics, the common thread is this — leadership has never been more complex. And those who invest in learning, relationships, and strategy will be the ones who stay ahead.
If you’re an in-house marketing leader looking for your people, check out DigitalStrategyExchange.com. You’ll find smart peers, honest insights, and the kind of support that’s missing from most industry events.
And if you’re enjoying these conversations, be sure to subscribe to Clarity Digital Pod for more honest talk from the front lines of marketing, technology, and leadership.
