Strategy & systems
I turn complicated customer, business, and technology questions into a direction people can understand and act on.
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 with a maker’s point of view.
For more than two decades, I’ve worked where strategy, experience, technology, and creativity meet. 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
The work takes many forms.
My role is usually to connect the pieces: customer needs, business ambition, creative thinking, technology, and the people responsible for making it real.
Product & experience
I shape useful digital products and experiences by connecting customer needs, design judgment, data, and delivery.
Marketing technology & AI
I explore how platforms, automation, and AI can improve the work itself—not simply add another layer of technology.
Leadership & teams
I bring disciplines and perspectives together, creating the clarity and trust teams need to do ambitious work well.
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.
Kaplan digital ecosystem
Enterprise strategy, architecture, CMS, design system, and product ownership for a multi-year transformation.
Read the story →Ecommerce growth
Digital product, experience, experimentation, and commerce strategy across a major education portfolio.
Read the story →From portfolio to product
How I used agentic development to build this production website, its publishing tools, connected APIs, and human-reviewed AI workflows.
Read the story →04 / Latest from the blog
Notes on the work.
Recent posts from my perspective as a digital strategy leader working across marketing, customer experience, product, technology, and AI.
AI · Agentic Commerce · Brand Strategy · Customer Experience · Product Strategy
Every Brand Is About to Have Two Customers
Brands increasingly serve two customers: people and the AI agents acting for them. Each needs a different experience built on the same promise.
Read →
What Building an AI-Native Website Changed About How I Lead Product
Building an AI-native website shortened the distance between product decisions and working software. The experience reinforced that faster delivery increases the importance of clear direction, disciplined prioritization, continual inspection, technical fluency, and human accountability. AI expanded what I could build, but it also made the product leader’s judgment more visible—and more consequential.
Read →
AI · Agentic Commerce · Website
The Website Isn’t Dying. Its Monopoly Is.
Agentic commerce is reshaping product discovery and purchasing. Brand websites will remain essential—but they may no longer control the customer journey.
Read →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.