Digital strategy & transformation
I shape customer journeys, business models, enterprise transformation, and omnichannel content strategy.
Jonathan
Sullivan.
For more than two decades, I’ve led digital strategies that drive growth, performance, and measurable business impact.
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01 / About
I bridge the gap between innovation and execution.
I’m a digital strategy, experience, commerce, and product leader with more than 21 years of experience shaping human-centered, high-impact digital experiences. My career has spanned Fortune 200 companies and top-tier agencies, giving me a rare blend of strategic vision, technical fluency, and creative instinct.
My work is anchored in digital commerce, product management, UX strategy, marketing optimization, AI, and automation. I lead complex transformations, global teams, and data-driven roadmaps designed to create measurable business growth and customer impact.
02 / How I lead
How I move
business forward.
AI for digital strategy
I apply AI to content, personalization, experimentation, asset creation, and workflow automation.
Product & technology leadership
I lead digital products, scalable platforms, MarTech integration, data strategy, and measurement.
Leadership & operations
I align global teams, stakeholders, and roadmaps around measurable outcomes.
03 / Selected impact
Evidence behind
the strategy.
Transformation matters when it creates measurable customer and business outcomes.
Kaplan digital ecosystem
Enterprise strategy, architecture, CMS, design system, and product ownership for a multi-year transformation.
Read the evidence →Ecommerce growth
Digital product, experience, experimentation, and commerce strategy across a major education portfolio.
Read the evidence →Conversion at scale
Year-over-year growth in online appointment bookings, supporting more than $1B in annual treatment-plan value.
Read the evidence →From portfolio to product
How I used agentic development to build this production website, its custom publishing tools, connected APIs, and human-reviewed AI automation.
Read the evidence →04 / What colleagues say
Leadership,
in their words.
Perspectives from people who have worked alongside me, reported to me, and partnered with me on transformation.
Jonathan is a creative, data-driven, and collaborative leader. His ability to quickly explain anything—to any audience—regardless of how technical is a rarity in this business.
Chad Ballew ↗Creative Director · Kaplan
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05 / Latest notes
What has my attention.
Short observations on technology, culture, food, family, and whatever else I’m thinking about.
A$AP Rocky asked a designer to rework his logo, and instead of quietly securing the job, he posted the DM for clout. Rocky canceled the project. What makes it worse is I actually enjoyed his logo redesign videos. He’s clearly talented, but whew… what a shame. He fumbled a huge opportunity for a moment of clout. 😭 A painful lesson.
View on Threads ↗If my MacBook Air M5 supported touch and could use the Apple Pencil I'd be so happy!
View on Threads ↗Forgot how much of a presence Lwaxana Troi has on DS9. What begins as her pursuing an uninterested Odo becomes one of the show’s most tender relationships. When they marry in “The Muse,” it may be a strategy to protect her and her unborn child, but Odo’s vows reveal something real. He loves Lwaxana deeply, just not romantically, and she respects that their friendship matters too much to ask him to be someone he isn’t. Beautiful reminder that love does not have to be romantic to be meaningful.
View on Threads ↗06 / Beyond work
Curiosity doesn’t clock out.
Based in Chicago, I’m also a proud beagle dad, amateur photographer, and frequent traveler who loves capturing the world through a creative lens. Whether I’m architecting a new digital experience or editing golden-hour shots, I bring the same curiosity, clarity, and care.
View photo galleries ↗
07 / Connect