Principal Product Manager

Role 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.

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!). 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, including WireGuard behavior, DERP relay expansion and capacity, subnet routers, exit nodes, and client-side networking.
• 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 customers use such as subnet routers, exit nodes, and Peer Relays.
• Own the application-layer connectivity surface — App Connectors, Services, DNS, and network segmentation.
• Own the operator control surface: how network engineers and IT admins configure, segment, monitor, and troubleshoot their networks at scale.
• 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 "weird" networks.
• Partner with GTM, Customer Success, and Solutions Engineering on production traffic commitments, regulated deployments, and strategic enterprise deals.
• Represent Tailscale's dataplane externally to enterprise customers, cloud partners, infrastructure vendors, and the networking community.

Qualifications

• 10+ years in product management owning networking, transport, edge, or infrastructure products at scale.
• Deep networking fluency across the stack: comfortable below the L4 on routing, NAT traversal, MTU/MSS, congestion, latency, and packet loss.
• Demonstrated ability to define performance commitments and customer-facing SLOs.

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.
• 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.
• 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.
• A competitive total compensation package including base salary, equity, and comprehensive benefits.
• Comprehensive group benefits with no waiting period for health, vision, dental, and more.
• Remote first company with flexibility in work location.
• Employer-funded retirement contributions with matching.
• Opportunities for personal and professional development with $1500 USD annually for professional development.
• Flexible paid time off program.
• A build-your-own home office setup with company-owned laptop and reimbursement for home internet.
• Paid parental leave program with top-ups for new parents.