Principal Product Manager (Dataplane)

Tailscale develops software that securely interconnects people and devices across networks. The Principal Product Manager will lead the dataplane platform, setting its vision and roadmap while driving performance, reliability, connectivity strategy, operational tooling, and customer-facing networking capabilities.

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)
• 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