Principal Product Manager

About the role

Tailscale is seeking a Principal Product Manager to guide the evolution of its core data transport layer. This role is central to ensuring Tailscale's promise of fast, secure, and reliable connectivity for millions of users and critical infrastructure. You will shape the future of how devices and services connect across the internet.

Key facts

What you'll do

• Define the strategic direction and product roadmap for Tailscale's data plane, encompassing WireGuard integration, relay network expansion, subnet routing, exit nodes, and client-side networking.
• Establish clear performance benchmarks and reliability standards as customer-facing product requirements.
• Oversee the complete product strategy for connectivity, including global network capacity, relay health, private relay solutions, and compliance with regulatory deployment needs.
• Drive the development of operational tools for customers, such as subnet routers and exit nodes, focusing on high availability, route management, and production readiness.
• Own the product aspects of application-layer connectivity, including how AI agents, CI/CD pipelines, and Kubernetes workloads access essential cloud resources.
• Develop the user interface and command-line tools that network administrators use for configuration, segmentation, monitoring, and troubleshooting at scale.
• Collaborate with design leads to translate complex networking systems into intuitive and effective product features.
• Improve connectivity success rates and debuggability across diverse network environments, including various NAT types, operating systems, and enterprise firewalls.
• Partner with Go-to-Market, Customer Success, and Solutions Engineering teams to incorporate customer feedback and production learnings into the product roadmap.
• Act as a subject matter expert on Tailscale's data plane, engaging with enterprise clients, cloud partners, and the broader networking community.

Requirements

• Minimum of 10 years of product management experience focused on large-scale networking, transport, edge, or infrastructure products. This includes experience with CDNs, edge platforms, SD-WAN, overlay networks, cloud networking, service mesh, API gateways, DNS/traffic management, or identity-aware proxies.
• Strong understanding of the networking stack, from lower layers (routing, NAT traversal, MTU, congestion) to application layers (overlay routing, proxies, DNS, network segmentation).
• Proven ability to define performance targets and customer-facing service level objectives, and to manage products under real-world production constraints.

Nice to have

• Familiarity with VPN and tunneling protocols like WireGuard, IPsec, or OpenVPN, or with low-level networking stacks such as kernel or eBPF.
• Experience managing globally distributed infrastructure, including capacity planning and regional expansion.
• Knowledge of routing protocols like BGP, MPLS, cloud VPC peering, or data residency requirements.
• Experience with application-layer connectivity solutions like service mesh, API gateways, DNS, proxies, or network segmentation.
• A track record of building administrative consoles and CLIs for network engineers and IT administrators.
• Background in regulated industries such as finance, healthcare, or government.
• Public contributions to technical writing, conference presentations, or open-source networking projects.
• Hands-on experience using Tailscale in a professional or personal capacity.

Skills & tools

• Networking protocols and architecture
• Product strategy and roadmap development
• Performance and reliability engineering
• Cross-functional collaboration
• Technical communication

Practical notes

• Compensation range: $197,000 - $246,000 USD base salary.
• Benefits include comprehensive health, vision, and dental coverage with no waiting period, employer-funded retirement contributions (0.75% match), and a $1500 annual professional development budget.
• Remote-first company with support for home office setup, including a company-provided laptop and monthly internet reimbursement.
• Paid time off and a paid parental leave program (20 weeks for birthing parents, 16 weeks for non-birthing parents).
• AI-assisted tools are used in the hiring process, with all final decisions made by humans.
• Official communications will come from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses.