MailMates
AI-powered Gmail assistant focused on improving email productivity
Owned the full technical stack and solved the key reliability challenges: cross-context authentication and stable UI injection in Gmail's unpredictable DOM
Key Contributions
- Created Chrome extension with seamless Gmail integration
- Implemented AI-powered email assistance features
- Built real-time synchronization with Firebase
- Designed and developed the Chrome extension
- Built AI-powered features for email assistance
Architecting a Resilient AI Assistant for Gmail
Principal Engineer
Challenge
The objective was to build MailMates, a Chrome extension bringing AI utilities (summaries, smart replies) directly into Gmail. The core engineering challenge was reliability within a hostile environment: Gmail's DOM is obfuscated, dynamic, and frequently updated by Google. The solution required a seamless UX that felt native to Gmail while managing shared state across a distributed architecture spanning extension background scripts, content scripts, and web applications.
- Gmail's obfuscated DOM uses dynamic alphanumeric class names that change unpredictably with updates
- Extension-to-web-app authentication required secure token synchronization across isolated contexts
- AI request loads needed to be handled without creating bottlenecks in billing verification logic
Solution
I architected a multi-layered system designed for resilience and maintainability. Rather than fighting Gmail's obfuscation directly, I integrated InboxSDK to decouple feature logic from Gmail's rendering engine. This strategic abstraction drastically reduced maintenance burden and allowed the team to focus on feature velocity instead of patching broken selectors. The backend infrastructure was built on .NET Core for its raw execution speed, mature dependency injection ecosystem, and robust concurrency management.
- InboxSDK integration for stable Gmail UI injection, eliminating brittle DOM parsing
- High-performance .NET Core backend for usage tracking and billing with excellent concurrency handling
- Next.js frontend with hybrid static/server-side rendering for optimal UX and SEO
Results
Zero maintenance overhead from Gmail DOM changes due to InboxSDK abstraction
Seamless single sign-on experience across extension and web application
Immediate premium feature access after web authentication without re-login
High-performance billing verification with no bottlenecks under heavy AI request loads
Native-feeling Gmail integration with no perceptible latency on UI injection
Engineering Approach
The most complex technical challenge was cross-context state management. Synchronizing authentication between a browser extension and a web application is non-trivial due to CORS policies and sandbox security boundaries. I implemented a secure token handoff mechanism enabling users to log in via the website and instantly access premium features in the extension. While InboxSDK handled 90% of UI injection, specific features required custom implementation. I engineered a robust observer pattern to detect Gmail's obfuscated class changes, allowing safe injection of custom buttons without triggering race conditions or memory leaks.