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 established the decision framework that reset this product's direction—auditing design-system constraints, evaluating tradeoffs with engineering, and defining what to preserve, simplify, or cut so the product could 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 caught between a platform team enforcing strict Redwood compliance and a product leader pursuing visionary concepts that might justify a native app—or at least push Redwood into mobile-native territory.

The PWA architecture was locked before I joined. The existing vision work wasn't buildable within it. And the team had a reputation for ignoring process.

I needed to figure out which parts of the vision were worth fighting for, which constraints were genuinely immovable, and what a path to production actually looked like when you stopped pretending otherwise.

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 six non-compliant patterns across hundreds of instances to understand exactly where the real friction was.

Rebuilt

Restored cross-functional trust by demonstrating compliance and adopting the platform team’s own established process.

Negotiated

Identified ten innovations scoped for platform adoption. Showing the vision with real constraints was more persuasive than pure aspiration.

Delivered

Shipped the core touchless flow first. Delivery earned far more credibility than any vision decks of mocks.

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

What started as damage control became a model for how Redwood-compliant work could get done on this and all mobile projects. The team with a reputation for ignoring process ended up establishing a process others followed.

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 6 months. First Redwood mobile product with integrated telemetry.

The Insight

Leadership had legitimately competing priorities. Both were reasonable, but neither fully compatible. My job was to find the overlap where something real could ship and each side could see their work reflected in it.