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. About the Role 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 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 What We Are Looking For 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 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 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 As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set. CAN Pay Range $263,980 — $329,640 CAD Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic! What We Offer An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life. A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles). Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family! Remote first company —most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description. Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation. Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration. Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities. Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own. Paid parental leave program . We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents). Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter. Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people. Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses.