Jonathan Riley smiling in a dark fedora in his creative workspace

About me

A creative foundation, a strategic mindset

I’m a multidisciplinary design and marketing leader with 20+ years of experience connecting design, technology, product, and brand. With 16 years focused on healthcare and health insurance, I bring deep industry knowledge to creating experiences that simplify complexity, improve engagement, and deliver meaningful results.

My work bridges creative execution and business strategy, helping organizations translate complicated challenges into intuitive products, cohesive brands, and effective marketing experiences.

  • Design thinking
  • Healthcare expertise
  • Collaboration
  • Strategic leadership

My approach

Design with purpose, build together, move forward

I bring a balance of creative craft, strategic thinking, technical understanding, and industry knowledge to every project. My approach is grounded in collaboration, empathy, and a focus on measurable outcomes.

  • Understand the problem

    I take time to listen, learn, and challenge assumptions, understanding both user needs and business objectives before defining a solution.

  • Build collaboratively

    I connect people, perspectives, and disciplines to create stronger solutions and move complex initiatives forward.

  • Stay close to the craft

    I remain involved from early concepts through execution, ensuring strategic decisions translate into thoughtful, well-executed experiences.

  • Focus on impact

    I design and build experiences that are usable, accessible, and aligned with meaningful business and user outcomes.

Experience & perspective

A career that blends multiple disciplines

My background spans UX design, product strategy, brand marketing, and front-end development. This combination allows me to see the bigger picture, bridge gaps between teams, and create cohesive experiences across the entire product and brand journey.

Having worked across both product development and commercial marketing, I understand how user experience, product value, brand positioning, and business objectives connect. I bring that broader perspective to the teams and organizations I support.

20+
Years of creative and
digital experience
16
years in healthcare
and health insurance
7+
Core disciplines

Industry experience

Making complex healthcare experiences easier to navigate

Over 16 years in healthcare and health insurance, I’ve developed a deep understanding of health plans, member experiences, healthcare technology, and the challenges of communicating complex benefits and services.

My work has spanned insurance enrollment, health plan member applications, wellness platforms, care navigation, and healthcare technology marketing. These experiences have given me insight into both the people using healthcare services and the organizations responsible for delivering them.

I understand the importance of balancing regulatory requirements, business objectives, accessibility, and usability in an industry where clarity and trust are essential.

That knowledge allows me to contribute beyond design execution, helping teams identify opportunities, navigate industry complexity, and develop solutions grounded in real healthcare needs.

Areas of experience

  • Health plan & benefits experiences
  • Insurance enrollment & member engagement
  • Digital health & wellness platforms
  • Care navigation & healthcare technology
  • Healthcare product & brand marketing

A creative background

A lifelong interest in the visual arts

My early foundation in drawing, painting, and printmaking continues to influence how I think about composition, storytelling, and design.

These creative disciplines shape my eye for detail, my appreciation for craft, and my approach to solving problems through visual communication. They remain an important part of how I explore ideas and develop creative solutions.

Explore my fine art gallery
Painting of a potted plant against a checkered background
Graphite portrait drawing
Colorful printmaking portrait with leaves
Mixed-media figure with patterned backdrop

Beyond the screen

Creative exploration across disciplines

Outside of product and brand work, I enjoy photography, film, graphic and print design, digital art, web development, drawing and painting, and printmaking. These interests keep me curious, inspire new ideas, and continually influence my approach to design and problem-solving.

  • Camera and film reels on a desk

    Film and photography

  • Screen-printed shirt, playing cards and print pieces

    Graphic and print
    design

  • Web design layouts on monitors with wireframe sketches

    Web design
    and development

  • Paint palette and brushes overlooking the coast

    Drawing and painting

  • Vintage printing press with inked linocuts

    Printmaking

Let’s connect

Interested in working together?

Whether you’re building digital experiences, developing a brand, or navigating the complexities of healthcare technology, I’d welcome the opportunity to connect.

I’m always open to new opportunities, interesting conversations, and collaborative projects.