About the Position

WatchGuard is looking for a Director of AI Product Management to own the strategy and execution for Rai, our agentic, AI-powered action layer built on WatchGuard Cloud, WatchGuard’s MSP focused security platform. This is a high-impact role at the intersection of agentic AI, cybersecurity, and the managed services market.

Rai handles the MSP workforce jobs that are structured, repeatable, and grounded in data that already lives in WatchGuard Cloud. It doesn’t just surface information; it closes loops. This PM owns what those loops look like, how reliable they are, and how MSPs learn to trust and extend them.

Reporting to the Chief Product Officer, this individual will be responsible for driving the Rai product roadmap, working cross-functionally with engineering, design, channel, and go-to-market teams, and ensuring that WatchGuard’s AI platform delivers measurable value to MSP partners.

A Day in the Life

As a Director of AI on the Platform team, you will work at the center of one of WatchGuard’s most strategically important investments. You will spend your time in direct conversation with MSP partners, understanding how they staff their SOCs and NOCs, where their technicians lose time, and what it would mean to their business to have those hours back. You will translate that understanding into agentic workflows that Rai can own autonomously, and work with engineering to define how those workflows behave when data is incomplete, confidence is low, or actions cannot be undone. AI tools are a native part of how you work; you use them to synthesize customer research, accelerate discovery, apply Spec Driven Design principles to structure requirements before engineering picks them up, and validate prototypes faster than traditional methods allow. You evaluate AI feature quality not just by adoption but by accuracy, reliability, and the degree to which MSPs choose to expand Rai’s scope over time. You drive roadmap alignment across a cross-functional team using working prototypes and real partner feedback, and you partner with PMM and the channel to ensure that what gets built also gets understood and sold.

If this role sounds like the work you’ve been building toward, we’d like to hear from you. Submit your resume and a brief note on what drew you to this problem space. Cover letters are optional — tell us what matters to you, not what you think we want to hear.