Stabilizing Payments to Unlock 251% Transaction Growth

Redesigning transaction infrastructure to unlock scale and stabilize growth.

ROLE Head of Design

FOCUS Consumer + Merchant Experience

TIMELINE 2022 - 2023

$2M

Annual Revenue Lift

Revenue unlocked through transaction stabilization

50%

Dispute Rate Reduction

0.69% → 0.33%

20%

Increase in Engineering Velocity

Design system + QA institutionalized

The Inflection Point

Upside wasn’t just facing payment instability — it was operating on aging infrastructure with plateauing growth and declining user trust.

  • 10-year-old app architecture limiting iteration speed

  • Inconsistent UI patterns across growth surfaces

  • Revenue growth plateauing

  • Payment disputes nearing Stripe’s termination threshold

01 STRATEGIC FRAMING

Dispute Ratio

.69%

Near Stripe’s 0.75% termination threshold — creating existential payment risk.

Dispute Burn

$18.8k

Operational drag driven by chargebacks.

Internal NPS

-32

Design + engineering misalignment slowing delivery and trust.

Capped Rollout

25%

“Pay with App” restricted to a fraction of users due to dispute instability.

Rebuilding the Core Experience

Upside’s consumer app was constrained by legacy infrastructure, inconsistent UI patterns, and no shared system foundations. We rebuilt the product to enable velocity, trust, and scalable transaction growth.

02 CONSUMER APP

CORE SYSTEMS

  • Introduced Upside’s first unified design system — component library, tokens, and documentation — enabling consistent UI patterns and accelerating engineering delivery.

  • Rebuilt the 10-year-old app infrastructure and modernized the full mobile experience. Standardized navigation, visual hierarchy, and interaction patterns across surfaces.

  • Added in-app wallet functionality and structured payment flows, enabling secure on-platform transactions and reducing operational risk.

  • Redesigned sign-up and authentication flows to reduce friction, improve account security, and support scalable user growth.

  • Rebuilt merchant discovery with improved location clarity, proximity logic, and redemption pathways — reducing friction from browse → claim → transact.

FUNCTIONAL PROTOTYPE

Deep Dive: Wayfinding

Discovery friction limited transaction intent.
We redesigned maps and offer discovery to create clearer merchant proximity, real-time savings visibility, and a predictable redemption path.

03 MERCHANT DASHBOARD

Unlocking Merchant Clarity

As Upside expanded from fuel into grocery and multi-vertical retail, the merchant tooling lagged behind the product vision.

We rebuilt the information architecture and rewrote system-level microcopy to support:

  • Surface-level metrics were replaced with structured reporting — impressions, redemptions, payouts, and ROI in one unified view.

  • Evolved the model from single-vertical fuel offers to configurable grocery and retail campaigns.

  • Rebuilt search to support shots, designers, and services — transforming discovery into intent-driven matching.

04 BRAND + GROWTH

Building Trust and Expanding Reach

Upside was perceived as transactional and low-trust.

We partnered across marketing and product to reposition the brand around:

  • Consumer savings credibility

  • Merchant transparency

  • Clear economic exchange

This included:

  • Full visual refresh and reskin across mobile

  • Brand system modernization

  • Performance marketing landing pages

  • Campaign creative for grocery expansion

Growth became product-led and brand-reinforced.

05 DESIGN OPS + CULTURE

Building the system behind the system.

Upside’s design function lacked structure, shared standards, and cross-functional clarity.

To sustain product transformation, we rebuilt how design operated — embedding process, ownership, and strategic alignment across product and engineering.

    • Established structured design reviews tied to roadmap milestones

    • Introduced decision documentation and async feedback loops

    • Reduced iteration churn and increased engineering throughput

    • Embedded designers within senior engineering pods

    • Clarified ownership across growth, marketplace, and payments

    • Shifted from surface-level requests to system-level outcomes

    • Facilitated system-mapping workshops across leadership

    • Reframed product strategy around transaction probability

    • Connected UX improvements directly to revenue mechanics

    • Introduced growth ladders and performance clarity

    • Improved internal team NPS (–32 → positive territory if you want to state directionally)

    • Increased retention and cross-team trust

System-Level Outcomes

-92%

Dispute Costs

+251%

Transaction Volume

#1

App Store Ranking

$2M

Annual Revenue Lift

Reflections

Upside’s growth challenge was not a single UX issue — it was a system misalignment between payments, trust, infrastructure, and organizational process.

Stabilizing disputes unlocked revenue. Rebuilding the app unlocked iteration speed. Restructuring design unlocked long-term scalability.

Growth doesn’t scale without operational clarity. Design, when embedded at the system level, becomes an economic lever — not a surface layer.

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Evolving discovery into an economic engine.
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Designing the first in-venue app.