Principal Product Manager – Dataplane

This is a fully remote position, open to applicants in Canada.

📋 Description

• Establish the vision and roadmap for the Tailscale dataplane, encompassing WireGuard functionality, DERP relay scalability and capacity, subnet routers, exit nodes, and client-side networking to ensure connectivity appears seamless and dependable.

• Articulate performance and reliability as product requirements from the customer's perspective.

• Oversee the connectivity product strategy comprehensively, including regional growth, capacity planning, relay health monitoring, enterprise and private DERP/Peer Relay solutions, and compliance with sovereign or regulated deployment standards.

• Steer the roadmap for operational components utilized by customers, such as subnet routers, exit nodes, and Peer Relays, focusing on deployment architecture, high-availability configurations, route management user experience, and production operational tools.

• Manage the application-layer connectivity interface—App Connectors, Services, DNS, and network segmentation—that influences how traffic reaches its destination and how AI agents, CI/CD, and Kubernetes workloads access necessary SaaS and cloud resources.

• Supervise the operator control interface, enabling network engineers and IT administrators to configure, segment, monitor, and troubleshoot networks at scale, utilizing both the admin console and the CLI.

• Collaborate closely with the embedded Network Features design lead to translate abstract networking systems into coherent, well-structured product interfaces.

• Control connectivity behavior across a comprehensive range of NAT types, operating systems, mobile carriers, enterprise firewalls, and unconventional customer networks, enhancing both success rates and customer troubleshooting experiences.

• Work in partnership with GTM, Customer Success, and Solutions Engineering on production traffic commitments, regulated deployments, and strategic enterprise agreements, converting customer insights into roadmap priorities.

• Act as a representative of Tailscale's dataplane to enterprise customers, cloud partners, infrastructure vendors, and the networking community, establishing credibility as a domain authority.

⛳️ Requirements

• Over 10 years of experience in product management overseeing networking, transport, edge, or infrastructure products at scale, including CDNs, edge platforms, SD-WAN, overlay networks, cloud networking, service mesh, API gateways, DNS/traffic management, or identity-aware proxies.

• Profound networking expertise across the entire stack: comfortable working below L4 on routing, NAT traversal, MTU/MSS, congestion, latency, and packet loss, as well as fluent at the application layer regarding overlay routing, proxies and connectors, DNS, and network segmentation—capable of engaging engineers from both teams as an equal.

• Proven track record in defining performance commitments and customer-facing SLOs, functioning under real production expectations, and effectively managing situations when systems do not meet those commitments.

🏝️ Benefits

• An inclusive, flexible environment where you can express your authentic self.

• A competitive total compensation package.

• Comprehensive group benefits without a waiting period.

• Remote-first company—most of our teams operate fully remotely.

• Employer-funded retirement contributions.

• Opportunities to connect with other Tailscalars in real life.

• Support for your personal and professional growth.

• Paid time off and a healthy work-life balance.

• A customizable home office setup.

• Paid parental leave program.