Over Two Decades of Transforming Ideas into Digital Reality

Jonathan Sullivan is a senior digital strategist and product leader with over 21 years of experience building innovative, human-centered digital experiences. With a career rooted in Fortune 200 corporations and top-tier agencies, he brings a rare mix of strategic vision, technical fluency, and creative instinct to every engagement.

His expertise includes product management, digital commerce, UX strategy, and marketing optimization—anchored by a deep knowledge of AI and automation. Jonathan actively leverages generative AI tools like ChatGPT, Google Gemini, and other LLMs to drive innovation across content creation, campaign ideation, asset generation (including image and video), and task automation. Skilled in prompt engineering, he helps teams unlock AI’s full potential—accelerating workflows, boosting personalization, and turning complex processes into scalable solutions.

From optimizing digital ecosystems to crafting intelligent customer journeys, Jonathan bridges the gap between innovation and execution. He’s led complex transformation projects, scaled global teams, and developed data-informed roadmaps that deliver real business results.

Based in Chicago, Jonathan is also a proud beagle dad, amateur photographer, and frequent traveler who loves capturing the world through a creative lens. Whether he’s architecting a new digital experience or editing golden hour shots from his latest adventure, he brings curiosity, clarity, and care to everything he does.

Core Expertise

Jonathan brings a strategic, customer-first mindset to every digital initiative. His work in this space is rooted in aligning digital experiences with business objectives to drive measurable growth.

    • Digital Experience Strategy & Customer Journey Design

    • Digital Business Model Innovation & Monetization

    • Enterprise Digital Transformation & Change Management

    • Content Strategy, Distribution & Omnichannel Media Planning

    • Digital Product Management & Scalable Platform Development

    • Marketing Technology (MarTech), AI Integration & Automation Tools

    • Data Strategy, Measurement Frameworks & Advanced Analytics

    • CRM Automation, Personalization & Lifecycle Marketing

    • E-commerce Strategy, Conversion Optimization & Performance Marketing

    • Cross-Functional Team Leadership & Global Stakeholder Alignment

    • Prompt Engineering for both creative and operational tasks

    • Automated Content Generation for web, email, social, and SEO

    • AI Image & Video Asset Creation using generative tools

    • Workflow Automation to streamline digital marketing and operations

    • Personalization Strategy powered by AI-driven insights and segmentation

    • AI Testing & Optimization for UX experiments, messaging, and conversion flows

Recommendations

  • “Jonathan is a champion for digital transformation... Every quarter the executive team would sit in amazement at the progress the team accomplished.”

  • “His ability to set the vision and objective right helped the team to work at a phenomenal level... One of the most rewarding and refreshing experiences to have worked with Jonathan!“

  • “His passion and leadership skills, along with his ability to communicate clearly, make him a great leader.“

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