Case Study — Breaking the Cycle and Shipping the Product

Christopher Kobar
5 min readMar 29, 2025

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How I helped bridge a bold design vision with the reality of shipping a product to real users

In 2004, I began my freelance writing career working on a tabletop role-playing game about vampires. I’d written similar material before, so I assumed this project would be easy. It wasn’t. I had to navigate oversight from a creative director, tight constraints, and looming deadlines. I quickly learned that waiting for perfection would jeopardize my livelihood. So I delivered the best work I could, ensuring the book shipped — and that I would be invited back.

Quotation: “Perfection if the enemy of progress” — Winston Churchill
“Perfection if the enemy of progress” — Winston Churchill

That early lesson stuck with me. Years later, it helped me deliver again.

The Challenge

A visionary product in need of a launch plan

I joined a product team working on a long-anticipated mobile expenses app — a cornerstone of our ERP suite — driven by a bold vision called Touchless Expenses. It promised a consumer-grade experience using real-time transaction data and automation through a unique partnership with JP Morgan. The design was ambitious, forward-looking, and had been carefully shaped through years of iteration and deep executive involvement.

The product had benefited from the creativity and dedication of designers before me — each building on the vision and adding important insight and depth. What had emerged was imaginative, polished, and clearly aimed at delivering something exceptional. But as the team approached the first pilot launch, a key question emerged: was it buildable?

A Familiar Tension

Design system vs. product vision

All teams were expected to adhere to the enterprise design system — Redwood — which, while still evolving, was a strategic priority. Our head of design had set a clear objective: 100% compliance, with any exceptions requiring a formal waiver.

Side-by-side comparison of the mobile phone app landing page before and after my contributions, calling out unbuildable design system deviations
Side-by-side comparison of the mobile phone app landing page before and after my contributions, calling out unbuildable design system deviations

When I reviewed the app, I noticed several areas where the design deviated from system standards. These deviations had often been made with the user in mind, attempting to elevate the experience beyond what Redwood could currently support. However, given the importance of compliance and the realities of our development environment, I saw an opportunity to step in and help the team close the gap between visionary design and practical implementation.

What I Did

Building on what came before

Rather than treat these deviations as mistakes, I approached them as the outcome of an ambitious and necessary design exploration. My goal was not to replace the vision, but to translate it into a deliverable product within the constraints we had.

Side-by-side comparison of the mobile phone app issue resolution design before and after my contributions, calling out unbuildable design system deviations
Side-by-side comparison of the mobile phone app issue resolution design before and after my contributions, calling out unbuildable design system deviations

With my experience using Redwood from its earliest iterations, I audited the design, identified areas of non-compliance, and began working component-by-component to align the product with the system — without losing sight of the product’s intent or user goals. Where compromises were necessary, I looked for ways to document the need for future improvements, ensuring we could revisit them down the road.

Cross-Functional Collaboration

Closing the gap with people, not just pixels

Shipping meant working across roles and disciplines to keep things moving forward:

  • With developers: I partnered with tech leads and engineers to understand feasibility, explain design intent, and support their learning of Redwood. My extensive experience coding front-ends gave us a shared foundation to build on.
  • With product managers: They helped me get up to speed on user behavior and legacy features. I brought them into design tradeoff discussions, ensuring we stayed aligned on outcomes and priorities.
  • With product designers: I frequently consulted peers on my team and others to validate design changes and surface better alternatives already available in the system.
  • With the design system team: I reviewed enhancement requests (ERs), closing those that no longer aligned with current priorities, and rewrote key ones with broader product applicability and clearer documentation.
Photo of a bridge under construction
Photo by Deny Hill on Unsplash

Restoring Alignment

Reconnecting product and platform teams

One major challenge involved a key component that had been designed in collaboration with the system team, but had been set aside by the product team during a period of rapid iteration. Unaware of this, the system team was preparing to release their version, which now conflicted with the implementation in our app.

I took the initiative to trace the history, understand both perspectives, and bring the teams back together. With open dialogue and mutual respect, we agreed to revisit the component collaboratively. That effort remains ongoing but is now close to resolution — with shared ownership and shared benefits.

While there were challenges along the way, the relationship between our product team and the design system team strengthened through close collaboration, mutual respect, and a shared willingness to compromise when needed — ultimately advancing our shared strategic goal of implementing the design system across all new products.

The Outcome

A launch grounded in reality, driven by vision

We successfully launched the product to an initial group of 20 users. That number grew tenfold within a year and reached around 1,000 the next. The most important result? We proved the core hypothesis.

  • The “touchless” model worked. Users preferred it over manual processes.
  • We identified clear paths forward. From usability feedback to system gaps, we learned what needed to improve and where opportunities existed for new enhancements to improve the experience.
  • We delivered a real, usable product. And that meant we could now iterate based on real insights.
Timeline of user growth from 21 in April 2023 to more than 1,200 in April 2025
Timeline of user growth from 21 in April 2023 to more than 1,200 in April 2025

No, the mobile app wasn’t a perfect, native-like, consumer-grade experience — yet. But that wasn’t failure. That was progress. We’d taken an ambitious vision and brought it to life in a real-world context, setting the stage for future enhancements.

What I Learned

Vision is critical — but only when paired with execution; they are two sides of the same coin. The work of those before me wasn’t something to fix; it was something to build on. By grounding that vision in what could be shipped, we turned possibility into momentum.

Shipping is how we learn. Design is how we listen. And collaboration is how we move forward.

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Christopher Kobar
Christopher Kobar

Written by Christopher Kobar

I love crafting experiences that make our lives simpler, more enjoyable, and more meaningful. I am the Kobarbarian.

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