Testing Mindsets, Team Innovation, and the New Era of Marketing with Wil Reynolds, Founder of Seer Interactive
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My conversation with Wil Reynolds was one of those episodes that immediately shifted how I think about marketing leadership. Wil is the founder of Seer Interactive, one of the most respected digital agencies in the game, known for its data-driven approach and ability to see around corners in search analytics and strategy. But this wasn't a typical agency founder interview—this was about thriving in uncertainty, building teams that can adapt, and why this moment in marketing feels eerily similar to the early 2000s SEO days.
From the start, it was clear that Wil operates from a fundamentally different headspace than most agency leaders. This wasn't about client retention strategies or service offerings—it was about embracing chaos, fostering a testing mentality, and building organizations that can pivot when nobody knows what they're doing.
When Nobody Knows What They're Doing: The Early 2000s SEO Parallel
Wil's comparison of today's marketing landscape to early 2000s SEO immediately grabbed me. "Super fast. No one knows what they're doing," he said, describing both eras. But instead of being intimidated by that uncertainty, Wil is energized by it.
"Some people are just built for spending a lot of time on something and then getting punched in the face and being like, well, that didn't work and getting up the next day. Some people aren't built for that."
That mindset—the ability to find joy in failure and get excited about industry resets—is what separates teams that thrive from those that get left behind. Wil's approach isn't about having all the answers; it's about building systems and cultures that can adapt faster than the competition.
The Hard Truth About Team Dynamics Right Now
One of the most striking parts of our conversation was Wil's brutal honesty about team management in this moment. He had to tell his entire company: "This is not the company for you if you want certainty."
"The things that got you from A to B won't get you from B to C. This is an innovation season. You have to wake up every day being comfortable trying to reinvent yourself."
What hit me hardest was his acknowledgment that companies might need to push people out who don't fit the current vision—especially when the job market makes it unlikely they'll leave on their own. It's not popular to talk about, but Wil's thinking is clear: he can't care more about someone's career than they do.
From Content Volume to Operational Transparency
Wil shared a perfect example that crystallizes how the game has changed. In traditional search, Banana Republic could throw some text on their website about being "environmentally friendly" and potentially rank. But in an LLM world, that surface-level content doesn't cut it.
"I can now understand that the word water usage means environmental friendliness. I can now understand that fair wages means that. So now they're like, okay, if we're talking about ethical clothing manufacturers, they already know what to expect."
The example he used—Nudie Jeans vs. Banana Republic—was eye-opening. Nudie Jeans, with their genuine transparency about manufacturing processes, wins in AI search because they're actually the right answer. You can't fake operational transparency when algorithms understand context at that level.
Cross-Divisional Marketing: The $40K Google Ads Revelation
Wil dropped an insight that should terrify every paid search manager: One client was spending marginally on YouTube but had 40% of their search terms triggering videos in the top 5 results. Meanwhile, 80% of their Google Ad spend was on terms that showed YouTube videos, but only 2% of budget went to YouTube.
"You take all your paid search terms and see how many of them are triggering YouTube in the top five. You add up how much of your spend that was on Google. My God, 80% of all your spend on Google triggers a video in the top five. How much are you spending on YouTube? 2%."
This is the kind of cross-divisional thinking that separates agencies that survive from those that don't. Wil's team regularly analyzes whether organic social can offset search traffic losses, what conversion rates look like across channels, and how to partner with other divisions instead of staying siloed.
Building Systems That Think Ahead
What fascinates me about Wil's approach is how he's building feedback loops that most agencies aren't even considering. He described a workflow using Claude's MCPs (Model Context Protocol) that connects email, calendar, call transcripts, and BigQuery data into one system.
"What calls did I have last week? Did I follow up with those people? What kind of questions did they ask? Are those questions different than the things they ask in the call itself?"
But it goes deeper. He can analyze client calls, check their assumptions against actual data in BigQuery, and surface insights from years of internal presentations—all without leaving Claude. It's the kind of systematic approach to client service that most agencies talk about but never actually build.
Personal AI: The Hotel Experience Workflow
On a personal level, Wil shared something brilliant: he records detailed notes about every hotel experience, then feeds them to ChatGPT. When planning trips, instead of getting generic "top 10 places" recommendations, he gets suggestions based on his actual preferences with his exact quotes referenced.
"I'm like, based on all the things that I loved about this hotel or this part of the city, what would you recommend and tell me why? And then I always say, put my exact quotes in."
It's a perfect example of how AI becomes exponentially more valuable when you feed it rich, personal context instead of relying on generic training data.
Key Takeaways for Marketing Leaders:
Embrace the testing mentality. If you're not comfortable with failure and rapid iteration, this moment in marketing isn't for you.
Operational transparency beats content volume. You can't fake your way into AI relevance with surface-level content.
Think cross-divisionally. The days of channel-specific optimization are over. You need to understand how paid, organic, social, and direct traffic work together.
Build systems for uncertainty. Create workflows that help you learn faster and adapt quicker than the competition.
Be honest about team fit. Not everyone is built for innovation seasons, and that's okay—but you can't let the wrong people slow down the right ones.
Talking with Wil was a reminder that the most successful marketers aren't the ones with the most experience—they're the ones most willing to throw out what they know and start learning again. Whether you're running an agency, leading an in-house team, or figuring out your own career path, his perspective is proof that uncertainty isn't something to fear—it's something to leverage.