Set the direction
Turn business goals and customer insight into a clear digital strategy—deciding what matters, where to invest, and what to do next.
Jonathan
Sullivan.
A personal site about the work I do, the ideas I’m exploring, and the things I care about.
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01 / Who I am
I’m a digital leader.I bring creativity, technology, and AI together to create meaningful, measurable experiences.
For more than two decades, that intersection has been where I feel most at home. I enjoy making complicated things clearer—whether that means shaping a digital platform, helping a team find its direction, or turning an emerging idea into something useful.
I’m naturally curious and comfortably multidisciplinary. My career has moved through design, marketing, ecommerce, product, transformation, and AI, but the thread has stayed the same: understand people, ask better questions, and build thoughtfully.
02 / What I do
How I lead digital.
My role is usually to connect the pieces: customer needs, business ambition, creative thinking, technology, and the people responsible for making it real.
Build connected experiences
Bring product, marketing, commerce, and technology together around experiences that work for customers and deliver business value.
Turn strategy into progress
Connect priorities, platforms, and ways of working so teams can move from plans to delivery, learn through experimentation, and scale what works.
Lead teams through change
Create shared purpose across functions, develop people, and build the trust and accountability needed to move complex work forward.
Shape what comes next with AI
Translate AI and agentic commerce into practical choices for brands—how to adapt as people and AI agents discover, evaluate, and buy.
03 / Selected work
A few things I’ve helped build.
These are selected stories from a longer career—work that combined strategy, teams, systems, and persistence to create something meaningful.
01
A production platform built with an AI-native workflow
How I used an agentic development workflow to build this production digital platform, its custom publishing tools, connected APIs, and human-reviewed AI automation.
02
A practical AI strategy focused on measurable value
A practical approach to AI adoption focused on better workflows, stronger customer experiences, faster experimentation, and measurable operating value.
03
One digital ecosystem for 100+ websites
Enterprise strategy, architecture, CMS, design system, and product ownership for a foundational transformation spanning Kaplan’s digital ecosystem.
04 / Latest from the blog
What I’m seeing. What it means.
Observations on AI, marketing, products, and customer experience, informed by the work of leading teams and putting digital strategy into practice.
When History Became Our Deadline: Working at a News Magazine on 9/11, 25 Years Later
Twenty-five years later, I remember witnessing 9/11 from an airport terminal and helping U.S. News cover its aftermath from Mississippi and Washington.
AI · AI Search · Brand Strategy · SEO · Digital Strategy
When AI Becomes the Front Door to Your Brand
As AI turns search results into answers, brands must become understandable, trustworthy, and worth choosing before a customer ever visits.
AI · Agentic Commerce · Product Strategy · Customer Trust · Digital Experience
Trust Is Becoming Product Infrastructure
AI turns trust from a brand message into product infrastructure built through accurate data, clear permissions, transparency, and human control.
05 / A note from a colleague
“Jonathan is a creative, data-driven, and collaborative leader. His ability to quickly explain anything—to any audience—regardless of how technical is a rarity in this business.”
Chad Ballew →Creative Director · Kaplan
06 / What I love
Looking closely.
Outside the workday, I’m a proud beagle dad, photographer, and frequent traveler. Photography gives me another way to notice people, places, architecture, and the small details that are easy to pass by.
Visit my photography site →
07 / Keep in touch
Thanks for stopping by.
If something here sparked a thought, you can find me on LinkedIn or send a note.