MAICON brings together top visionaries and experts in the field of AI during a three-day conference packed with actionable sessions and networking events—all to position you as the change agent your organization (and career) needs. In this ongoing speaker series, we’re featuring these extraordinary leaders, with forward-looking predictions, actionable tips you can use today, and a preview of their MAICON 2025 sessions.
Christopher S. Penn is the Co-Founder and Chief Data Scientist at Trust Insights, an internationally recognized thought leader in marketing analytics and AI. A bestselling author and acclaimed speaker, Chris has shaped five pivotal areas in the industry: the adoption of Google Analytics, data-driven marketing and PR, modern email marketing, marketing data science, and the integration of AI and machine learning into marketing strategy.
Long before tools like ChatGPT entered the scene, Chris began his AI journey in 2013, working with classical machine learning and developing custom software. This early work laid the foundation for co-founding Trust Insights in 2017 alongside his colleague Katie Robbert. Together, they’ve become leading voices in applied marketing AI.
You may also know Chris as the co-host of the award-winning Marketing Over Coffee podcast.
At MAICON 2025, Chris and Katie will lead a hands-on workshop designed to help marketers turn measurement into meaningful results through the power of AI.
Workshop Preview: Use AI to Deliver Insights, Not Crunch Numbers
Chris emphasized: “Do not let generative AI do math…ever.”
Instead, he recommends giving AI tools the math in its completed form. But that doesn’t mean doing it by hand. There are thousands of free, high-quality performance libraries (like Google’s CoLab) that can be integrated into your workflow to handle the heavy lifting.
Once these components are in place, marketers can use generative AI to turn raw data into focused reports and detailed dashboards tailored to specific stakeholders—helping overcome the data paralysis so many teams face.
In their workshop, Chris and Katie will demonstrate exactly how to build this process using live demos and practical prompts.
Lesson Learned: AI Is Evolving Faster Than You Think
AI technologies are evolving at an exponential rate, and being adopted even faster than expected.
Chris pointed to ChatGPT as an example. In just two years, the tool has progressed from occasionally producing correct answers to outperforming human PhDs in almost every field. He added that we are doubling AI’s capacity approximately every six months.
He explained:
“Every six months, it’s twice as capable. So, if AI can’t do a task today, it might be able to in just six months.”
And we’re still only scratching the surface. The broader implications of AI on industries and society remain largely unexplored. For marketers, the takeaway is clear: staying relevant means staying current with AI’s rapid evolution.
Looking Ahead: The Smartest Investment Is In Yourself
“We used to say that AI won’t take your job,” said Chris. “But with today’s capabilities, they are beginning to erode entry-level work.”
This is a strong impetus for professionals to skill up to meet and exceed the expected outcomes of their job responsibilities. Understanding what AI tools can do in your role makes it easier to meet rising expectations and stay ahead of the curve.
Chris’s advice? Now is the time to “invest heavily in yourself and your training if you want to remain relevant, like going to the MAICON conference.”
Links We Like
AI-Ready Marketing Strategy Kit
Overwhelmed by AI? Lacking a clear roadmap? This AI-Ready Marketing Strategy Kit, built on Trust Insights’ proven frameworks, empowers you to achieve measurable success.
Almost Timeless: 48 Foundation Principles of Generative AI
In Almost Timeless, Penn provides the definitive playbook. Drawing on 18 months of in-the-trenches work and insights from thousands of real-world questions, he distills the noise into 48 foundational principles—durable mental models that give you a permanent, strategic understanding of this transformative technology.
Explore the landscape of generative AI, from something as small as optimizing your LinkedIn profile to detailed use cases and strategy development.
Chris & Katie’s Workshop at MAICON
From Facts to Acts: How AI Turns Marketing Measurements Into Results
This workshop directly addresses marketing's most pervasive challenge: the endless accumulation of analytics data that sits unused and fails to drive decisions. Presented by TrustInsights.ai's CEO Katie Robbert and Chief Data Scientist Christopher Penn, this three-hour session transforms idle marketing data into actionable intelligence through generative AI techniques. The workshop specifically targets marketers who recognize they're collecting valuable measurement data, but struggle to extract meaningful insights or implement changes based on what they've gathered. By leveraging generative AI, participants will break through this data paralysis, dramatically accelerating analytics processes, while improving output quality.
Attendees will learn to systematically activate data by determining which marketing metrics are suitable for AI analysis and which require supplementary tools. The Trust Insights 5P framework provides a structured methodology that moves participants from data collection to implementation through a series of defined steps: defining ideal customer profiles, mapping AI-assisted customer journeys, conducting comprehensive SWOT analyses, developing channel-specific tactical plans, and creating detailed 90-day work plans.
Participants gain practical skills in generating marketing plans, developing data-driven strategies, analyzing individual channels, and conducting competitive analysis using publicly available information.
For optimal benefit, attendees should have a basic understanding of generative AI tools, access to platforms like ChatGPT or Claude, and familiarity with spreadsheets and marketing analytics systems. While sample data will be provided, participants are encouraged to bring their own marketing data to address specific organizational challenges.
This tool-agnostic workshop includes ample time for questions and hands-on practice, ensuring participants leave with the confidence to immediately apply generative AI to break through data paralysis.
Keep Up with Chris (and AI)
Discover more resources from Chris, and stay up-to-date on the latest in his AI journey.
- Follow Chris on LinkedIn
- Learn more about Chris and subscribe to his newsletter via his website.
- Read more about the work he’s doing at Trust Insights.
- Tune into his podcast Marketing Over Coffee.
Join Us at MAICON 2025
Marketing Artificial Intelligence Conference (MAICON) was created for marketing leaders and practitioners seeking to drive the next frontier of digital marketing transformation within their organizations.
We’re excited to host our 5th annual MAICON—Marketing AI Conference—at this pivotal point for our industry. Join us from October 14 to 16, 2025, in Cleveland, Ohio, and use the special code SPEAKERSERIES100 at checkout to receive $100 off your registration!
