A close-up of a gold-colored chain necklace with a circular pendant containing a small cross.

Hi, I’m Chris.

I design the large scale, complex, and AI assisted systems people depend on every day, figure out how to make them human-friendly, and ship ‘em.

Enterprise∙SaaS∙B2B/B2E/G2E/G2C∙30+ products∙20+ years

Chris Kobar and an AI bot contemplating a strange machine
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Where I Fit ∙ How I Work

Systems

● Enterprise platforms

● Regulated/internal tools

● AI-assisted workflows

Situations

● Stalled products

● Misaligned teams

● Vision–execution gaps

Approach

● Constraints ➞ clarity

● Clarity ➞ decisions

● Decisions ➞ ship

Case Studies

Expense review screen on a smartphone showing a taxi receipt, with faint abstract network lines in the background suggesting hidden system complexity.

Breaking the Stalemate

Shipping Oracle’s First Redwood Mobile Experience

The product had been stuck in redesign loops for three years. I helped the team stop relitigating the vision and start agreeing on what we could actually build—which became Oracle's first Redwood-compliant mobile release.

Shipped Oracle's first Redwood mobile experience after 3-year impasse

Scaled from 26-user pilot to 450+ cardholders within 8 months

Rebuilt cross-team trust while still pushing targeted innovation

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Bonus Oracle Expenses case study: Stopping the wrong AI delivery channel before it became irreversible. View the case

Strategic enterprise UI showing an AI-assisted ERP configuration workflow, with a conversational interface guiding changes alongside structured planning models and consolidation rules.

Slashing Consultant Costs with AI

Established the product north star for eliminating implementation consultants ($500K–$2M per customer) and unifying Oracle’s ERP and EPM experiences—defining AI interaction patterns and platform requirements in partnership with the Redwood Design System team.

This work reflects early-stage strategy and system framing; subsequent execution and delivery are still in progress.

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DCAC diagnostic platform unified workbench interface

An Expert Tool for Expert Users

Unifying Five Legacy Diagnostic Tools into a Single Workbench

I designed a diagnostic platform that replaced five legacy tools with a single workbench—for the engineers who keep customers' on-premise systems running.

Consolidated five legacy diagnostic tools into one unified platform

Designed for expert users with 20–30 years of domain experience

Shipped within one year of design handoff; became the primary diagnostic tool for on-premise support

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Full Product Archive: A complete list of every product I’ve worked on across my career, from early web systems to enterprise platforms. View all products

What I’ve been thinking

About Me

I’ve been drawn to design since childhood, always ready to take on a seemingly complex problem and wrangling it until I find that perfect balance of vision and reality. Whether large team or small, public sector or private, enterprise or consumer, I am always ready to step in to get the train moving again and to make the product and our team better.

Outside of work, I’ve taken a winding path and lived in a lot of different worlds—structured, creative, technical, and human. I write, I make things that aren’t tied to roadmaps, and I value craft for its own sake. That perspective keeps me grounded and shows up in how I work with others: thoughtful, curious, and genuinely human.

I’m currently playing with a lot of AI tools, discovering ways to simplify my life while accelerating my accomplishments, while cheering on my UConn Huskies basketball teams.

Photo of Chris Kobar wearing dark sunglasses and a white shirt. Chris is bald with s short goatee and mustache.