Ryan Ly | Software Engineer

About

Background & Focus

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Engineering • Architecture • UX

About Me

Staff Software Engineer with nearly a decade of full-time industry experience crafting resilient web platforms and intelligent systems.

Hi, I'm Ryan. I graduated from the University of Waterloo with a Bachelor of Computer Science (BCS) in 2017 and have been working full-time in the software engineering industry ever since.

Currently, I am a Staff Software Engineer at Felicity (askfelicity.ai), where we build enterprise AI software that transforms complex operations in regulated industries into reliable, autonomous systems.

Previously, I spent 8 years (2017–2025) at Square (Block) as a Tech Lead and Senior Engineer. During my time there, I led cash flow and money movement systems on Square Banking, served on the founding team for the Bill Pay 0 → 1 initiative, and engineered core features for Invoices. Earlier in my career, I completed software engineering internships at well-known technology companies across the Bay Area. After spending key formative years building in San Francisco, I am now based in Toronto.

Frontend Engineering

Deep expertise in TypeScript, React, Next.js, and Ember.js—crafting polished, mobile-responsive interfaces with sub-second performance and intuitive, accessible user experiences.

Full-Stack Architecture

Designing resilient backends, high-throughput APIs, and cloud infrastructure across AWS and GCP, backed by robust monitoring systems and comprehensive testing.

AI & Agentic Systems

Architecting autonomous AI agent workflows, model orchestration, tool calling, and high-reliability systems for regulated enterprise domains.

Experience

Career & Milestones

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Career Journey

Experience

A continuous track record of technical leadership, enterprise scale, and AI innovation.

SEPT 2025 – PRESENT

Staff Software Engineer

Felicity (askfelicity.ai) • Toronto, ON

Architecting enterprise AI software for regulated industries (healthcare and complex enterprise operations). Building autonomous AI workflows, agent self-healing systems, and high-reliability full-stack infrastructure.

2017 – 2025 (8 YEARS)

Staff / Senior Software Engineer & Tech Lead

Square (Block) • San Francisco, CA & Toronto, ON

Spent 8 years building critical products across Square's financial ecosystem:

Square Banking (Tech Lead): Led technical architecture for cash flow products, engineering critical money movement flows (inbound & outbound transfers for Square Checking and Savings) and high-reliability financial interfaces.
Bill Pay (Founding Team • 0 → 1): Part of the founding team that built and shipped Square Bill Pay from the ground up, taking it from inception to production.
Invoices Team: Contributed to key engineering initiatives early on, including recurring invoices, estimates, payment workflows, and the core orders model migration.

Co-op Experience

Software Engineering Intern

Apple • Sunnyvale, CA

Worked on improvements to an internal tool for Apple Maps that allowed operators to manage and update transit data worldwide.

2012 – 2017

Bachelor of Computer Science (BCS)

University of Waterloo • Honours Co-op

Comprehensive study in algorithms, distributed systems, human-computer interaction, and networks with six industry software engineering co-op terms.

View Complete Profile on LinkedIn

Tech Stack

Tools & Capabilities

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Staff Engineer Toolbox

Tech Stack

Core technologies, AI frameworks, cloud services, and architectures I leverage daily.

Frontend & Web Architecture

TypeScript React Next.js Ember.js Design Systems Modern CSS (Grid / Flexbox / Subgrid) Web Performance (CWV) State Management Vite & Tooling Accessibility (WCAG)

AI & Agentic Engineering

Vercel AI SDK AI Agent Frameworks & SDKs Tool Calling & Function Execution Structured Outputs Model Orchestration Autonomous Workflows

Backend & Languages

Ruby on Rails Node.js Python PostgreSQL Redis REST & GraphQL APIs Distributed Microservices

Cloud, Edge & Infrastructure

AWS (EC2, S3, CloudFront, Lambda) Cloudflare Fastly Vercel Supabase Docker Sentry Observability (Datadog, OpenTelemetry) CI/CD Automation

Projects

Products & Creations

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Featured Work

Projects

Selected consumer platforms, full-stack applications, and self-hosted smart home infrastructure.

PianoShelf

Co-Founder & Engineer

Visit PianoShelf

Co-founded a digital sheet music platform revolutionizing how musicians discover, share, and collaborate on piano sheet music worldwide. Built a high-performance REST API backend with client-side interactive viewer and community features.

Python Django TypeScript REST API Community

Chores Weekly

Creator

Visit Chores Weekly

A modern weekly chore planner and gamification app for households. Automates task distribution, tracks recurring duties, rewards XP for completion, and promotes household harmony with real-time sync.

React TypeScript Supabase PWA Vite

Smart Home & Networking

IoT Architecture & Homelab

Self-Hosted

Engineered a private, self-hosted smart home automation system and secure homelab network. Built with Home Assistant, custom Google Home integrations, smart switches, and sensors. Features secure remote mesh routing via Tailscale, network-wide DNS ad-blocking and privacy via AdGuard Home, and dedicated IoT subnet isolation.

Home Assistant Tailscale Mesh VPN AdGuard Home Google Home API Smart Switches VLAN & Networking

Contact

Let's Connect

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Get in Touch

Contact Me

Based in Toronto, ON (EST). Whether you'd like to discuss engineering challenges, AI workflows, or explore new opportunities, I'd love to chat.

Direct Email [email protected] Send Email →

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Open Source GitHub View Repositories →