Principal Product Manager (Dataplane)

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices. They are seeking a Principal Product Manager to lead the dataplane platform, responsible for driving the vision and roadmap, enhancing performance, and ensuring reliable connectivity for customers.

Responsibilities:

• Set the vision and roadmap for the Tailscale dataplane. This includes WireGuard behavior, DERP relay expansion and capacity, subnet routers, exit nodes, and client-side networking with the goal of making connectivity feel automatic and reliable
• Define performance and reliability as customer-facing product requirements
• Own connectivity product strategy end to end: regional expansion, capacity planning, relay health observability, enterprise and private DERP/Peer Relay offerings, and sovereign or regulated deployment requirements
• Drive the roadmap for the operational primitives customers use such as subnet routers, exit nodes, and Peer Relays including deployment topology, high-availability modes, route management UX, and production operational tooling
• Own the application-layer connectivity surface — App Connectors, Services, DNS, and network segmentation — that determines how traffic finds its destination and how AI agents, CI/CD, and Kubernetes workloads reach the SaaS and cloud resources they depend on
• Own the operator control surface: how network engineers and IT admins configure, segment, monitor, and troubleshoot their networks at scale, across both the admin console and the CLI
• Partner closely with the embedded Network Features design lead to turn abstract networking systems into legible, well-reasoned product surfaces
• Own connectivity behavior across the full matrix of NAT types, operating systems, mobile carriers, enterprise firewalls, and the "weird" networks customers actually run, improving both success rates and customer debuggability
• Partner with GTM, Customer Success, and Solutions Engineering on production traffic commitments, regulated deployments, and strategic enterprise deals, turning customer learnings into roadmap priorities
• Represent Tailscale's dataplane externally to enterprise customers, cloud partners, infrastructure vendors, and the networking community as a credible domain authority

Requirements:

• 10+ years in product management owning networking, transport, edge, or infrastructure products at scale: CDNs, edge platforms, SD-WAN, overlay networks, cloud networking, service mesh, API gateways, DNS/traffic management, or identity-aware proxies
• Deep networking fluency across the stack: comfortable below the L4 on routing, NAT traversal, MTU/MSS, congestion, latency, and packet loss, and equally fluent at the application layer on overlay routing, proxies and connectors, DNS, and network segmentation — able to engage engineers on both teams as a peer
• Demonstrated ability to define performance commitments and customer-facing SLOs, operate under real production expectations, and handle the moments when systems miss those commitments
• Familiarity with VPN/tunneling protocols (WireGuard, IPsec, OpenVPN) or low-level networking stacks (kernel, eBPF, userspace)
• Experience operating globally distributed infrastructure POPs, relays, and edge nodes including capacity planning, regional expansion, and the customer-visible performance tradeoffs that come with it
• Familiarity with subnet routing, BGP, MPLS, cloud VPC peering, or data residency constraints
• Experience with application-layer connectivity: service mesh, API gateways, DNS, proxies/connectors, or network segmentation and policy
• Track record building the operator control surface — admin console and CLI — that network engineers and IT admins use to configure and troubleshoot networks at scale
• Background in regulated industries (finance, healthcare, government)
• Public technical writing, conference talks, or open-source networking contributions
• Hands-on experience with Tailscale at work or home