Director, AI Product Management

WatchGuard Technologies • Miami, FL

14h

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.

Requirements

• Deep familiarity with how managed service providers operate, including how they structure their teams, price and deliver services, manage margin pressures, and where technician time goes. You understand that for MSPs, simplicity and automation are not features; they are the business case. You know the difference between a tool an MSP will actually adopt and one that adds process to an already stretched team.
• Demonstrated depth in product management, with meaningful hands-on experience shipping agentic AI or LLM-powered automation in a B2B context — typically 8+ years overall and at least 2 years working directly on autonomous or semi-autonomous AI workflows where the system takes action on behalf of the user. Candidates who have shipped real agentic products recently will be weighted over those with tenure alone.
• Hands-on familiarity with how LLMs work in production: context limits, latency tradeoffs, hallucination risks, and when RAG, fine-tuning, or deterministic fallbacks are the right answer.
• Experience defining evaluation criteria and quality standards for AI actions, including how to validate that an automated workflow is safe to run unsupervised.
• AI tools are part of your core workflow. You use them for customer research synthesis, Spec Driven Design, and prototype validation, getting to a well-structured spec faster and with more rigor than traditional methods allow. You think in terms of what AI can own end-to-end, not just where it can assist.
• Strong instincts for what makes an agentic feature genuinely useful versus impressive in a demo, especially in an MSP context where trust, reliability, and low-friction adoption determine whether a product survives the first 90 days.
• Comfort working across engineering, design, and go-to-market in a fast-moving environment.
• Clear, direct communicator who can move between technical depth and business narrative depending on the audience.

Nice To Haves

• Experience with MSP operational tooling including ConnectWise, Autotask, NinjaOne, or HaloPSA.
• Background in cybersecurity products, managed services, or multi-tenant SaaS platforms.
• Experience building or evaluating functional prototypes as a discovery and alignment tool.
• Understanding of responsible AI in production environments, including explainability, auditability, rollback behavior, and least-privilege action design.

Responsibilities

• Ensure the agents are monetizable and a commercial success. You will drive the ideation, design, and development of AI-powered agents and solutions, with a focus on creating monetizable agentic capabilities aligned to MSP market needs.
• Own the Rai product roadmap from discovery through delivery, balancing near-term partner value with the longer-term platform convergence vision.
• Define and prioritize agentic workflows that move MSPs from visibility to decision to action, replacing or extending MSP workforce jobs rather than just adding a chat interface.
• Establish evaluation frameworks for AI features, including how WatchGuard defines quality bars, measures accuracy and reliability, and decides when an automated action is ready for production.
• Work directly with MSP partners to understand workflows and pain points, and validate product direction through direct customer engagement.
• Drive alignment across engineering, channel, PMM, and leadership using working prototypes and real partner feedback. Clearly conveying the outcomes to each stakeholder.
• Own AI safety and reliability as a product responsibility, including how Rai behaves when confidence is low, when actions are irreversible, and when the MSP’s trust is on the line.
• Partner with PMM, channel, and sales to translate product capability into GTM strategy, partner messaging, and enablement.
• Define and track success metrics for Rai features: automation rate, ticket deflection, time-to-action, accuracy, and downstream business outcomes for MSPs.
• Monitor the AI and MSP platform competitive landscape to identify differentiation opportunities.

Benefits

• We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed