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 →04 / 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 ↗05 / Connect