Principal Product Manager (Dataplane)

About Tailscale

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.

Job Description

We are seeking a Principal Product Manager to lead Tailscale’s dataplane platform which is the critical layer that carries customer traffic and delivers the promise of “fast, secure, just works.“  This position will be responsible for driving forward open source & commercial technology spanning the Tailscale client, DERP, Subnet routers, WireGuard, Exit Nodes, Peer Relays, and App Connectors. See How Tailscale Works and How NAT Traversal Works to learn more.

Tailscale’s growth has significantly expanded the scope and importance of the dataplane. It now carries traffic for over 7 million monthly active devices (and growing rapidly!). Tailscale has quickly moved beyond just a VPN to providing critical engineering and AI infrastructure. Organizations depend not just on Tailscale to provide employee access to cloud environments - they also use Tailscale in the critical network path within and across their datacenters powering Humans, AI Agents, CI/CD workflows, and Kubernetes workloads.

When a user says “Tailscale just works,” they’re describing the dataplane choosing direct versus relay paths correctly, recovering cleanly from network changes, and staying invisible when everything is working. When an enterprise commits production traffic to Tailscale, they trust the dataplane to hold performance SLOs, reliability guarantees, and connectivity across difficult NAT topologies.

This role reports directly to Tailscale’s VP Product, Ross Kukulinski.

Key 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 custo…