Will Yi

CISSP | PMP | AWS Solution Architect | ScrumMaster

SEATTLE, WA

Endlessly curious.
Selectively rigorous.
Always securing.

18+
Years in Tech
11+
Years Leadership
Orchestrator
Leadership Style

Security & Software Engineering Leader · AI Platform Security

18 years in software, 11 of them at WatchGuard holding security validation and release sign-off for 10+ production security products across firewall, proxy, identity, endpoint, and Wi-Fi. My route into security ran through the release gate rather than the network operations center. I built the adversarial validation infrastructure that made security sign-off defensible: 3,000+ test scripts scaling automated coverage from 10% to 90% against injection, authentication bypass, and protocol-level fuzzing, with org-wide red-team methodology adopted as the standard across security product engineering. At Cisco I lead 9 engineers (7 FTEs and 2 contractors) building AI systems for 12M+ production devices. The current work is platform security for agentic AI: trust boundaries and least-privilege access for autonomous agents, model and output validation for AI-driven recommendations, and data integrity controls across distributed AI pipelines. One production rollout cut incident resolution time by 81%. The through-line is software lifecycle depth applied to security: knowing where vulnerabilities hide in the development cycle, and building controls developers can actually ship with. I am targeting Director of Platform Security and Head of Security Engineering roles where security architecture is the primary mission. I write about AI security at Outwire (outwire.ai), where I publish practical guidance for teams shipping AI applications and take on advisory work with those teams.

Beyond the Architecture

When I'm not securing infrastructure or optimizing workflows, you can find me logging miles on long-distance runs, playing guitar, or out on the golf course and badminton courts.

Platform Security AI Security Secure SDLC

Software Engineering Manager

Cisco Systems Inc.
2022 — PRESENT

Lead a team of 9 engineers (7 full-time employees and 2 contractors) delivering AI-driven wireless intelligence services for 12M+ production devices and 800K+ customers globally. Set technical direction, build the team, drive execution, and make sure security, reliability, and governance are designed in from the beginning rather than added after.

Beyond shipping secure code, I'm integrating AI security and threat modeling workflows into how the team develops software — making secure-by-design AI development a first-class part of the engineering process, not just an afterthought.

Platform Security AI Security Secure SDLC

QA Architect

WatchGuard Technologies Inc.
2011 — 2022

Trajectory: Staff QA Engineer -> Engineering Manager -> QA Architect. Held security validation and release sign-off for 10+ production security releases across firewall, proxy, identity, endpoint, and Wi-Fi. Built the adversarial validation infrastructure — 3,000+ test scripts scaling automated coverage from 10% to 90% against injection, authentication bypass, and protocol-level fuzzing — with org-wide red-team methodology adopted as the standard across security product engineering.

Scaled automated security linting and policy enforcement using Python, embedding compliance directly into distributed APIs, UIs, and CI/CD pipelines. Governed security architecture for 10+ major releases end-to-end, maintaining zero deployment delays while achieving a 7x growth in automated vulnerability and risk coverage.

AWS Security Cloud Architecture Python CI/CD MSSP Product Security

18 years in software and security engineering. QA Architect at WatchGuard (2011–2022). Software Engineering Manager at Cisco (2022–Present).

● Active AI · Productivity

Context Infrastructure

A personal AI workspace system — rules, memory, skills, and agent orchestration patterns that turn Claude into a persistent, context-rich second brain.

● Production ML · Networking

AI-RRM

AI-powered Radio Resource Management system for Cisco wireless networks. Applies reinforcement learning to optimize spectrum allocation and reduce interference at scale.

● This Site Astro · Design

wiyi.ai

This site. Built with Astro, Tailwind v4, and React. Designed as a living portfolio — the code and design are intentional artifacts, not an afterthought.

● Active AI · Engineering

AI Dev Workflows

A collection of agentic development workflows integrating Claude Code, parallel subagents, and structured memory into the software engineering process.

● In Progress Python · Imaging

Astrophoto Pipeline

Automated image stacking, calibration, and post-processing pipeline for deep-sky astrophotography. Built to handle raw sensor data from long-exposure sessions.

● Exploring Side Projects

Open to Build

Actively looking for interesting side projects and business opportunities — especially at the intersection of AI tooling, productivity, and knowledge management.

Half marathon finisher. Always training further.

Acoustic and electric. Finding rhythm in the noise.

Exploring the world with family — and documenting every moment along the way.

Open to great opportunities
and interesting conversations.

I'm currently exploring senior engineering leadership roles in Security Engineering and AI Security opportunities, and ambitious side projects. If you're building something that matters, or in the need to secure anything, let's talk. The inbox is open at hello@outwire.ai.

Threat Modeling Red-Team Engagements AI Security Architecture Executive Workshops & Training