MarTech Podcast: Navigating the AI Boom with Resilient Marketing

Date: October 20, 2025
Host: Benjamin Shapiro
Guest: Dave Steere, CMO of Webflow

Episode Overview

This episode dives deep into the seismic impact Artificial Intelligence (AI) is having on marketing, likening its transformation potential to the arrival of the commercial Internet or the iPhone. Benjamin Shapiro and Dave Steere explore why many marketers still treat AI as a superficial copywriting tool—rather than a revolution in customer experience—and provide practical insights on leveraging AI for personalization, website optimization, and strategic experimentation. The episode balances practical advice with engaging metaphors and honest discussion about embracing failure, the importance of creative differentiation, and the challenges facing marketing leaders in this fast-evolving age.

Key Discussion Points & Insights

1. AI in Marketing: From Copy Tool to Experience Shift

[01:15-06:34]

• AI is “Big Papi,” Not Doug Mankiewicz: Benjamin uses a Boston Red Sox metaphor to illustrate the difference between minor tech changes (Doug Mankiewicz) and era-defining shifts (David Ortiz/"Big Papi", i.e., AI).
• Widespread Underutilization: Only 20% of marketers are using AI agents to automate marketing, and most just for copywriting, missing the bigger opportunity for experience transformation.
  Quote – Benjamin Shapiro [01:15]:
  "AI isn't just another Martech tool. It's causing a universal change in how customers expect to interact with brands, but most marketers see AI as an assistant, not a tool to improve their personalization at scale."

2. Early Innings: Trust and Change Management

[06:34-08:26]

• Comparisons to the Dot-Com Era: Dave likens today’s AI landscape to the early internet—full of uncertainty, experimentation, and a need to build trust, especially regarding public adoption.
• People vs. Process vs. Tech: Technology changes fast, but people and processes lag—making true transformation slow and iterative.

3. Beyond Content: AI-Driven Personalization and Website Optimization

[09:50-12:05]

• Wave One → Wave Two of AI:
  • Wave One is AI for content generation (entry point).
  • Wave Two is using AI for "personalization on the website, testing and optimization at scale"—like running 100 A/B tests instead of just one.
  • AI can now identify which website elements to optimize based on user interaction data. Quote – Dave Steere [10:03]:
    "The practitioners that I see... they're thinking about how do I go from, let's say, wave one, which is content... to wave two... to create personalization on the website, to enable testing and optimization at scale."

4. The Impact of LLMs on the Buyer Journey and Website Strategy

[12:05-16:13]

• Rise of Answer Engine Optimization (AEO): Marketers now design their websites for two audiences—humans and LLMs (Large Language Models)—to ensure their content is surfaced in AI-driven research tools.
• Website Traffic Quality Over Quantity: As LLMs increasingly mediate the research phase, fewer—but more qualified—visitors arrive at websites seeking direct conversion.

5. Combating “Sea of Sameness” with Creativity

[16:13-17:58]

• Content Homogenization Risk: AI may lead to websites and content resembling each other, making creativity and storytelling a new (old) differentiator.
  Quote – Dave Steere [16:13]:
  "Your ability to be creative will be your competitive advantage and that will bring marketing back to its roots. That will bring us back to our storytelling roots..."

6. Experimentation, Failure, and Resource Optimization

[22:00-25:51]

• Embracing the Experimentation Graveyard: A healthy marketing culture accepts that many experiments will (and should) “fail” and be documented, sharing learnings openly.
  Quote – Dave Steere [22:24]:
  "The graveyard is a feature, not a bug. I think the sign of healthy experimentation is that you're going to fail. And failure is fine as long as you're failing fast and you're learning from it."
• Design Smart, Controlled Experiments: Effective experimentation requires hypotheses, controls, and post-mortems to capture learning, avoid wasted effort, and ensure incremental gains.

7. Incrementality vs. Direction: Maintaining a North Star

[25:51-30:39]

• Balancing Small Gains with Strategic Direction: Constant optimization shouldn't substitute for maintaining a clear vision or “North Star,” lest teams drift off track.
  Quote – Benjamin Shapiro [25:51]:
  "If we keep optimizing towards incremental gains, how do we make sure that we're still just pointed at the North Star?"
• Integrating Brand and Experimentation: CMOs must balance incremental experimentation with bold, brand-led moves based on market shifts and customer focus.

8. The Persistent Importance of Storytelling and Human Creativity

[30:39-32:28]

• AI as Copilot, Not Creator: AI can accelerate experimentation and support marketers, but only humans can craft authentic narratives that resonate.
  Quote – Dave Steere [31:32]:
  "Stories have been the thing that motivates people to take action… AI is going to be an assistant in, it's going to be a copilot in. But ultimately…the human is going to be at the center of that..."

Notable Quotes & Memorable Moments

• [05:21] Benjamin Shapiro:
  "Yeah, it's a big deal, right? This is an iPhone moment. It's gonna take 20 years to see this technology change roll out as opposed to, eh, this is a six months trend..."
• [13:44] Dave Steere:
  "You're now speaking to two audiences. You need a website experience… that will delight… but you're also speaking to robots."
• [16:13] Dave Steere:
  "In this environment, your ability to be creative will be your competitive advantage and that will bring marketing back to its roots..."
• [22:24] Dave Steere:
  "The graveyard is a feature, not a bug... What we do over here is we try to market in the open as much as possible."
• [31:32] Dave Steere:
  "Since the dawn of age, stories have been the thing that motivates people to take action… Ultimately, the human is going to be at the center of that."

Important Segment Timestamps

• 01:15 – Only 20% of marketers use AI automation
• 02:40-06:34 – Boston sports metaphor: AI’s transformational role
• 09:50 – Moving beyond content: Personalization and dynamic optimization
• 13:44 – Websites now speak to both humans and LLMs (AEO)
• 16:13 – Creativity as a competitive edge in an AI-optimized world
• 22:24 – The culture of experimentation and the value of failure
• 25:51 – The challenge of maintaining strategic direction amid continual experimentation
• 31:32 – Storytelling, creativity, and the persistent human role in marketing

Episode Tone & Takeaways

The conversation is energetic, anecdotal, and full of humor (sports and traffic metaphors abound), but always circles back to clear, tactical insights. Both speakers emphasize that while AI is fundamentally shaking up marketing, the biggest winners will be the organizations that experiment openly, embrace failure, and infuse their work with creativity and storytelling to remain truly differentiated as AI becomes ubiquitous.

Final Thought [32:28 - Show Close]:
"There’s always an art and science to marketing… Artificial intelligence can help us with the experimentation, but it can't help us figure out that balance between the scientific and the creative as well." – Benjamin Shapiro

For more resources, connect with Dave Steere on LinkedIn, visit martechpod.com, or check out webflow.com.