Note: The job is a remote job and is open to candidates in USA. Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices. They are seeking a Principal Product Manager to lead the dataplane platform, responsible for driving the vision and roadmap, enhancing performance, and ensuring reliable connectivity for customers.
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
Skills
- 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, 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
Benefits
- An inclusive, flexible environment where you can be your authentic self.
- 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).
Company Overview
Company H1B Sponsorship