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
01 / 03
05 / Latest thinking
Ideas in practice.
Short perspectives on digital strategy, marketing, customer experience, and AI.
AI · Agentic Commerce · Website
The Website Isn’t Dying. Its Monopoly Is.
Agentic commerce is changing the role of brand and ecommerce websites. As AI agents increasingly handle product discovery, comparison, and purchasing, the website may no longer control the entire customer journey. Instead, it becomes both a trusted destination for brand depth and the underlying source of product data, commerce capabilities, and customer confidence wherever the journey takes place.
Read →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