Jordan Denning

Checkout Platform Migration (Orders)

• Contributed to Square’s largest checkout architecture migration from the legacy Bills API to the Orders platform, scaling adoption 28% → 96% of POS checkouts (~8.8B transactions).
• Improved checkout reliability by reducing fallback mode usage 97% (11.5M → 352K monthly).
• Contributed to improvements in offline payment reliability, part of a resilience program protecting ~4M Square sellers.

MarketUI Checkout Modernization (Technical Lead)

• Led iOS development of the MarketUI checkout redesign, managing 2–4 engineers and migrating tender types including Cash, Cash App Pay, Bitcoin, QR payments, and house accounts; also implemented key checkout experiences including signature capture, tipping, and receipt selection and delivery flows.
• Designed modular payment architecture and dependency injection infrastructure enabling scalable tender integrations.
• Delivered an A/B experiment across 8.5M checkouts, resulting in +3.7% tipping rates and –1.7% cancellation rate.

Neighborhoods (Technical Lead)

• Led iOS implementation of Neighborhoods, integrating Cash App local commerce features into Square POS checkout.
• Built merchant brand card UI, QR-based customer check-in, and push notification workflows connecting Square POS and Cash App.
• Coordinated development across iOS, Android, backend, product, design, and data science teams.

AI Development Workflow

• Designed AI-assisted development workflows by writing Linear tickets with structured architectural context to guide AI agents toward relevant files and system patterns; also built AI skills that generated screen and tender scaffolding (state, events, UI, workflow tests, snapshot tests), enabling parallel development across engineers and accelerating large-scale migrations.

• Rebuilt and launched a consumer mobile application that reached #1 in its App Store category.
• Developed features across iPhone, iPad, tvOS, and watchOS, collaborating closely with design and QA.