Principal Product Manager (Dataplane)

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

About the Role

We are seeking a Principal Product Manager to lead Tailscale's dataplane platform, the critical layer that carries customer traffic and delivers the promise of "fast, secure, just works." This position will drive open source and commercial technology spanning the Tailscale client, DERP, Subnet routers, WireGuard, Exit Nodes, Peer Relays, and App Connectors. Tailscale's dataplane now carries traffic for over 7 million monthly active devices and powers critical engineering and AI infrastructure, including employee access to cloud environments, AI agents, CI/CD workflows, and Kubernetes workloads.

Responsibilities

• Set the vision and roadmap for the Tailscale dataplane, including WireGuard behavior, DERP relay expansion and capacity, subnet routers, exit nodes, and client-side networking to make 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 operational primitives 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 for AI agents, CI/CD, and Kubernetes workloads.
• 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 NAT types, operating systems, mobile carriers, enterprise firewalls, and customer networks, improving success rates and 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 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 as a peer.
• Demonstrated ability to define performance commitments and customer-facing SLOs, operate under production expectations, and handle incidents when systems miss commitments.

Nice to Have

• 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 customer-visible performance tradeoffs.
• 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 — for network engineers and IT admins 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.

Benefits

• An inclusive, flexible environment where you can be your authentic self, with recognition of diverse voices and backgrounds.
• A competitive total compensation package, including base salary, equity, and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period: health, vision, dental, and more for you and your family.
• Remote-first company with virtual and in-person social events, and a corporate co-working program (e.g., WeWork).
• Employer-funded retirement contributions: dollar-for-dollar match up to 0.75% of eligible compensation.
• Annual company retreat, team off-sites, and opportunities for in-person collaboration across Canada, the United States, the United Kingdom, and Singapore.
• $1500 USD annually for professional development, mentorship, coaching, and internal promotion opportunities.
• Flexible, paid time off for any situation, supporting work-life integration.
• Build-your-own home office setup: company-owned laptop (Mac or PC), monthly home internet reimbursement, and $500 USD to customize your workstation.
• Paid parental leave: 20 weeks for birthing parents, 16 weeks for non-birthing parents.

Pay

US Pay Range: $197,000—$246,000 USD