Katie Robbert, Co-Founder and CEO
Katie Robbert is the co-founder and CEO of Trust Insights, the data analytics and AI consultancy she founded with Christopher S. Penn in 2017. As CEO, she sets the company’s strategy and oversees its growth, operations, and product commercialization, running the business side of a data analytics firm. Under her leadership, Trust Insights has built its reputation on teaching clients how to think about their data so they can act on it themselves, rather than handing over a dashboard and walking away. She also leads AI workshops and training, helping teams put AI into practice the right way.
Her career began in pharmaceutical research, where data was high-stakes and accuracy was non-negotiable. There she led teams of Microsoft Partner software engineers developing software to reduce pharmaceutical abuse. Over more than 20 years, she moved into marketing technology and then AI strategy, building multi-million dollar lines of business in martech, pharma, and healthcare.
A self-described accidental AI expert, she leads a data analytics company without a computer science background. Her work centers on the part most AI projects overlook: the people. The 5P Framework by Trust Insights™ (Purpose, People, Process, Platform, Performance), her best-known creation, gives teams a structured way to plan before investing in technology. She is the creator and instructor of Trust Insights flagship course, The AI-Ready Strategist.
Katie is a featured speaker at MAICON, the Marketing AI Conference and serves as an instructor for the AI Academy from SmarterX. She continues to take the stage to educate audiences about AI, Organizational Behavior, and where the two intersect. She is a published author with papers in the Pharmacoepidemiology and Drug Safety journal and Applied Marketing Analytics.
She was also named a Women in AI Leadership Rising Star finalist and holds an M.S. in Marketing and Technological Innovation from Worcester Polytechnic Institute.
Christopher S. Penn, Co-Founder and Chief Data Scientist
Christopher S. Penn is an internationally renowned keynote speaker who energizes audiences with his expertise on artificial intelligence in marketing. A recognized thought leader, he demystifies complex AI concepts, providing practical strategies that empower marketers to achieve breakthrough results. Christopher’s insights on leveraging AI for data analysis, content creation, and strategic decision-making have shaped five key trends in the marketing industry: Google Analytics adoption, data-driven marketing and PR, modern email marketing, marketing data science, and AI/machine learning in marketing. His journey in AI began in 2013, a decade before tools like ChatGPT brought the technology into the mainstream, giving him a deep understanding of its potential and practical applications. His engaging and informative presentations leave attendees with actionable takeaways they can implement immediately.
As co-founder and Chief Data Scientist of Trust Insights, Christopher leads a team of experts dedicated to helping businesses unlock the full potential of their data using cutting-edge AI solutions. His proven track record of success includes building AI-powered systems that have delivered double-digit ROI for prominent brands such as Cisco Systems, T-Mobile, Citrix Systems, GoDaddy, AAA, McDonald’s, Twitter, and many others. He is a 2025, eight-time IBM Champion in IBM Data and AI and co-host of the award-winning Marketing Over Coffee marketing podcast. He is a published author in the Journal of Applied Marketing Analytics, and his work is also reflected in over two dozen marketing books, including the bestselling “Almost Timeless: 48 Foundation Principles of Generative AI“.
Download a full-resolution headshot of Mr. Penn here.
Get to know Christopher S. Penn >
John J. Wall, Partner and Head of Business Development
John J. Wall speaks, writes and practices at the intersection of marketing, sales, and technology. As Partner and Head of Business Development, he is responsible for managing all aspects of sales and customer success.
He is the producer of Marketing Over Coffee, a weekly audio program that discusses marketing and technology with his co-host Christopher S. Penn, and has been featured on iTunes. Notable guests include Ann Handley, David Meerman Scott, Debbie Millman, Simon Sinek and Seth Godin. His work has been profiled by Forbes, CBS Evening News, NECN, The Boston Globe, Boston Herald, DM News, and the Associated Press.
John was previously the Vice President of Marketing at EventHero. He has held positions specializing in Customer Relationship Management, Marketing Automation and sales support systems at both venture funded and privately held businesses, working with clients such as Microsoft, Oracle, and Salesforce.com. Read more on LinkedIn.
John has lived in every corner of the United States and now resides outside of Boston. Check out his twitter stream to hear what he’s rambling on about and here’s some more personal stuff.
Kelsey Richard, Account Manager
Kelsey Richard is the Account Manager at Trust Insights, acting as the essential link between high-level strategy and daily execution. Known for her open-communication style, she prioritizes transparency and truth to keep projects on track. Kelsey is a firm believer that in an increasingly digital world, human connection matters most.
Her professional approach is defined by a fearless adaptability and the willingness to jump in and do whatever needs to be done, regardless of the challenge. This “all-in” mentality was forged during multiple years as a patient advocate, the restaurant industry, retail, and finance. Whether fighting for a patient or managing humans within intimidating environments, Kelsey is driven by a lifelong commitment to helping others and doing whatever it takes to make sure the job gets done.
Gini Dietrich, Board Member and Advisor
Gini Dietrich is the founder and CEO of Arment Dietrich, an integrated marketing communications firm. She is the author of Spin Sucks, co-author of Marketing in the Round, and co-host of Inside PR. She also is the lead blogger at Spin Sucks and is the founder of Spin Sucks Pro.
