Reagan Middlebrook
Senior Software Engineer | Founder, CEO, & CTO @ Cupbearer.app | Open to Staff/Senior Software Engineer Roles
- Role
- Founder at Cupbearer, Llc
- Location
- Seattle, WA, US
- LinkedIn followers
- 500 followers
About Reagan Middlebrook
Software Engineer with 10 years of experience across backend, full-stack, and mobile. Good at finding systemic problems others have missed — a PHI logging vulnerability across 55 production repos, a monitoring blind spot leaving 38 of 73 data queues silently unalerted, a company-wide PagerDuty integration that no one had previously solved — and drive the architectural remediation end to end.At Indeed I led a 0-downtime redesign across 5 microservices that increased DAU 30% and message volume 20%. Before that I spent two years at Snapchat shipping features to a global audience, including leading the localization of Context Cards that drove a 509% increase in context menu DAU.I also founded Cupbearer, a cross-platform iOS/Android app I\'ve built solo, which pushed me deep into privacy compliance — GDPR/CCPA flows, Global Privacy Control, third-party library auditing — and the product tradeoffs of building without institutional support.
Experience
Founder
Jun 2025 — Present
Education
Seattle Central College
Computer Science
2012 — 2013
University of Washington Tacoma
Bachelor of Science (B.S.), Computer Science and Systems
2014 — 2016
Skills
- Leadership
- Html
- Java
- Dart
- Css
- Time Management
- Flutter
- Python
- Javascript
- Team Leadership
- Linux
- C
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