Breaking the Stalemate

2022–2023 · Enterprise SaaS · Financial Operations · Oracle

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

Diagram illustrating a workflow process involving a circular chart with segments labeled 'Ideation,' 'Reopen,' 'Deviation,' and 'Engineering.' Superimposed is a smartphone screen showing a receipt for a steakhouse in San Francisco, with details of the transaction and a green autosubmitted message. To the right, there is a screenshot of a mobile app interface for reviewing expenses, including an image of a bowl of ramen with chopsticks, expense details for an employee meal at Olive Garden, and options to add a receipt, cancel, or choose no receipt.

The loop I broke

I owned the decision framework that reset this product’s direction—auditing design-system constraints, evaluating tradeoffs with engineering, and making the call on what to preserve, simplify, or cut so the product could finally ship.

Impact

✓ Shipped to first enterprise customers within 9 months

✓ Scaled from 26-user pilot to 450+ cardholders within 6 months

✓ First Redwood mobile product in production with integrated telemetry

✓ Rebuilt platform-product trust while delivering targeted innovation

The Problem

Three years. Five designers. Zero launches.

The product was stuck between a platform team demanding strict Redwood compliance and a leader chasing visionary designs that might justify a native app—or at least expand Redwood in mobile-native directions.

The PWA architecture was locked before I arrived. The vision work wasn't buildable within it. And my team was seen as renegades who ignored process.

I had to ship something real—while satisfying both sides.

Zoomed-out view of a Figma file showing dozens of mobile expense app concepts, explorations, and iterations created over multiple years—none of which shipped.

Three years of vision work. None of it shippable within platform constraints.

My Approach

Diagnosed

Mapped 6 non-compliant patterns across hundreds of instances

Repaired

Rebuilt trust with platform team by following their process correctly

Threaded

Proposed 10 innovations scoped for platform adoption—vision signal without compliance risk

Shipped

Core touchless flow first; earned credibility for v2

Screenshots of a mobile app for reviewing and submitting expense reports with images of Asian meals, including a bowl of noodles, a glass of iced tea, and a small dish of sauce; a notification about a payment transfer from Oracle Apps.

The shipped product: compliant, functional, and the foundation for everything that followed.

The Outcome

The approach taken here became the foundation for future Redwood-compliant mobile work, restoring confidence in the platform and establishing a repeatable path for aligning ambitious product vision with system constraints.

Slide showing three-phase rollout: Phase 1 (May 2023) with 26 cardholders and 69 expenses auto-created; Phase 2 (August 2023) with 112 cardholders and 2,579 expenses auto-created; Phase 3 (January 2024) with 450 cardholders and customers going live.

Phased rollout from pilot to 450+ cardholders within 8 months. First Redwood mobile product with integrated telemetry.

The Insight

Leadership wasn't misaligned by accident. They wanted different things. My job wasn't to pick a side. It was to find the overlap where something could ship while each stakeholder saw their priorities reflected.