A close-up of a gold-colored chain necklace with a circular pendant containing a small cross.
Chris Kobar and an AI bot contemplating a strange machine

Hi, I’m Chris.

I shape the strategy, structure, and experience of large-scale enterprise systems—turning complexity into clarity so teams can ship with confidence

Enterprise∙SaaS∙B2B/B2E/G2E/G2C

My Zone

Systems

Enterprise platforms at scale

Regulated and internal tooling

AI-integrated product experiences

Situations

Stalled or directionless products

Cross-functional misalignment

Strategy-to-execution gaps

Approach

Turn constraints into framing

Turn framing into alignment

Turn alignment into shipped outcomes

Culture

Cross-functional partnership

High autonomy, high accountability

Clarity over consensus

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

After three years of stalled redesigns, I reframed the problem to move the team from debating the vision to aligning on a shippable scope—resulting in 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

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

Defined the product north star to eliminate implementation consultants ($500K–$2M per customer) by unifying Oracle's ERP and EPM experiences—establishing AI interaction patterns and platform requirements with the Redwood Design System team.

This represents strategic product framing; execution is ongoing.

DCAC diagnostic platform unified workbench interface

An Expert Tool for Expert Users

Unifying Five Legacy Diagnostic Tools into a Single Workbench

I led the design of a diagnostic platform that consolidated five legacy tools into a unified workbench—built 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

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

On My Mind

About Me

I've spent my career working at the intersection of complex systems and the people who use them—finding the balance between product vision and what can actually ship. Whether the team is large or small, public or private sector, I bring the same thing: clarity on what matters, and the momentum to act on it.

Outside of work, I've moved through a lot of different worlds—structured, creative, technical, and deeply human. I write, I build things untethered from roadmaps, and I value craft on its own terms. That range shows up in how I work: I bring genuine curiosity and a grounded perspective to every collaboration.

I actively work with emerging AI design and development tools—using them to prototype, explore interaction patterns, and sharpen how I think and build. I'm also developing a podcast and remain a devoted UConn Huskies fan.

Photo of Chris Kobar