Jim Silverman · Enterprise Product Designer

I untangle complex systems to make work feel simple.

For over 15 years, I’ve specialized in unravelling the knots of enterprise software. By bridging business strategy and human needs, I turn fragmented tools and messy requirements into streamlined experiences that make work easier and more productive.

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Hi. I’m Jim Silverman, enterprise product designer.

I’ve spent over a decade in the trenches of high-scale enterprise SaaS, Fintech, and Insurtech. My expertise lies in finding the threads of clarity within chaotic legacy environments and turning them into cohesive product strategies.

Most recently at ADP, I’ve been unravelling the complexities of global service platforms for 18,000+ users, integrating Agentic AI to move the needle on operational efficiency. Before that, at ProSight and SPS Commerce, I pioneered digital transformations that replaced manual, error-prone processes with automated, self-service ecosystems.

Learn work about my skills and past work →

I lead teams through ambiguity.

Enterprise software is rarely straightforward. I partner closely with engineering and product to take messy, undefined problems and turn them into clear, actionable design strategies. My role isn't just about crafting interfaces. It's about building consensus, answering the hard questions early, and getting everyone aligned and moving in the exact same direction.

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Jim is one of those really hard-to-find designers who can blend a wealth of technical know-how with top-notch design skills. Jim's ability to deal with ambiguity is off the charts. He has the rare ability to extract meaning from fuzzy and disjointed requirements and assimilate it into a meaningful design.

Chuck
Chuck Mallott, Design Director at SPS Commerce

Let's work together.

Like what you see? Great to hear! Even if I’m not actively on the job hunt, I’m always curious about interesting challenges and love hearing about opportunities to make an impact.

Here’s what I look for in a role:

  • 100% Remote: I work best from my own environment. Having spent years in the 4-hour commute grind, a remote-first culture is non-negotiable for my productivity and my family.
  • Deep Complexity: I love turning chaotic, complicated interfaces into experiences that feel clear, simple, and efficient.
  • Workflow Products: I’m happiest when I’m making someone’s day easier, their work faster, and their tools more enjoyable to use.
  • Individual contributor: I want to lead the work, not the org chart. I thrive when I can shape the big-picture vision and mentor the team without the overhead of people management.

If your role checks these boxes, don't hesitate to reach out →