Chicago, IllinoisDigital Strategy Leader

Jonathan
Sullivan.

For more than two decades, I’ve led digital strategies that drive growth, performance, and measurable business impact.

Jonathan Sullivan

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 / Expertise

Strategy that moves
business forward.

01

Digital strategy & transformation

Customer journeys, business model innovation, enterprise transformation, and omnichannel content strategy.

02

AI for digital strategy

Prompt engineering, automated content, generative asset creation, personalization, experimentation, and workflow automation.

03

Product & technology leadership

Digital product management, scalable platforms, MarTech integration, data strategy, measurement, and advanced analytics.

04

Leadership & operations

Cross-functional team leadership, global stakeholder alignment, and roadmaps that connect vision to measurable outcomes.

03 / 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 journal

04 / Connect

Let’s build what’s next.

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