Square
Empowering millions of sellers through safer, faster, and smarter point-of-sale experiences.
🏦 Squaring Up Engineering Excellence at Square
At Square, I’ve driven critical efforts across infrastructure, developer experience, and AI enablement, shaping how engineers write code, how sellers complete transactions, and how core systems evolve behind the scenes.
🧠 Fortifying a Core Path for Every Transaction
Early on, I identified an unstable Core Data pattern that powered every transaction across Square’s suite of point-of-sale apps. The code path was fragile, lacked guardrails, and introduced subtle but severe bugs across teams. I initiated and led a multi-phase effort to install compile-time safety nets around these Core Data fetching operations.
To solve this, I architected and shipped a declarative, type-safe predicate system, drastically improving safety and readability. The system:
- Reduced Core Data development and code review time by 40%
- Prevented dozens of potential bugs from ever reaching production
- Was open-sourced to benefit the broader Swift and iOS community
It’s now a foundational pattern adopted across Square’s iOS codebases, protecting seller transactions at the source.
🤖 Building AI Tooling in the Early Days of the Gold Rush
At the dawn of the generative AI boom, I founded Square’s internal Copilot for Xcode working group, identifying a tooling gap for iOS engineers before most were even experimenting with LLM-assisted coding. I navigated the end-to-end process:
- Initiated a rigorous security review
- Partnered with legal and compliance to secure organizational approval
- Configured and distributed the toolset across all iOS engineers at Block
This initiative not only unlocked generative coding assistance — it helped shape Square’s early developer experience around AI.
Since then, I’ve continued championing AI-powered developer tooling and accelerating technical workflows wherever I see opportunity. From internal advocacy to executive alignment, I’ve consistently pushed these conversations forward, even writing directly to our CEO to highlight wins and unblock higher-leverage investment. My belief is simple: if every engineer shared one small win, the compounding effect would be enormous.
These efforts reflect a broader pattern in my work: not just solving hard problems, but making better engineering contagious.
🧰 Championing Developer Ergonomics
I’m obsessed with eliminating friction and ceremony in the engineering process. At Square, I’ve:
- Introduced the first Swift macro in production, leveraging Swift 5.9 to generate boilerplate and enforce compile-time constraints
- Advocated for macro adoption across teams, helping engineers streamline verbose patterns with safe, expressive code
🗂️ Leading Through Stewardship and Systems Thinking
Some of my most impactful work hasn’t been flashy. It’s been in spotting and fixing slow-burn problems others overlooked:
- Rescued a core localization API that had lost ownership after a reorg, facilitating documentation, knowledge transfer, and team alignment to reestablish long-term stewardship
- Consolidated scattered internal documentation into a single searchable repo, reducing documentation discovery time from minutes to seconds and significantly lowering onboarding friction
- Led a multi-stage, cross-org rollout of a jointly owned checkout experience, coordinating across multiple technical and product teams to ensure alignment and stability for every Square seller
Whether I’m building safety nets in critical code paths, rolling out AI tools across an org, or quietly removing friction from the engineering process, my focus is the same: make great engineering inevitable. At Square, I’ve had the opportunity to lead with vision, build with precision, and raise the bar for what excellence looks like, both in the code and in the culture.
