Principal Product Manager (Dataplane) - Tailscale

About Tailscale

Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices. Founded in 2019 and fully distributed, we are 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—the critical layer that carries customer traffic and delivers our promise of "fast, secure, just works." You will drive open source and commercial technology spanning the Tailscale client, DERP, Subnet routers, WireGuard, Exit Nodes, Peer Relays, and App Connectors.

Key Responsibilities

• Vision & Roadmap: Set the strategy for the dataplane, including WireGuard behavior, DERP relay expansion, and client-side networking.
• Performance & Reliability: Define customer-facing product requirements, performance commitments, and SLOs.
• Connectivity Strategy: Own end-to-end strategy for regional expansion, capacity planning, relay health, and enterprise/private offerings.
• Operational Primitives: Drive the roadmap for subnet routers, exit nodes, and Peer Relays, including high-availability and operational tooling.
• Control Surface: Own the operator experience for network engineers and IT admins across the admin console and CLI.
• Cross-Functional Leadership: Partner with design, engineering, GTM, and Customer Success to turn technical systems into intuitive product surfaces and strategic enterprise deals.
• Domain Authority: Represent Tailscale’s dataplane externally to partners, customers, and the networking community.

What We Are Looking For

• 10+ years in product management owning networking, transport, edge, or infrastructure products (e.g., CDNs, SD-WAN, service mesh, API gateways).
• Deep networking fluency: Comfortable with L4 routing, NAT traversal, MTU/MSS, congestion, and packet loss, as well as application-layer concepts like proxies and DNS.
• Proven ability to define performance commitments and operate under real production expectations.

Nice to Have

• Familiarity with VPN/tunneling protocols (WireGuard, IPsec) or low-level networking stacks (eBPF, kernel).
• Experience operating globally distributed infrastructure POPs and relays.
• Background in regulated industries (finance, healthcare, government).
• Hands-on experience with Tailscale at work or home.

What We Offer

• Competitive total compensation (base salary + equity).
• Comprehensive group benefits with no waiting period.
• Remote-first culture with annual company retreats and team off-sites.
• $1,500 USD annual professional development budget.
• Monthly home internet reimbursement and $500 USD home office stipend.
• Paid parental leave program (20 weeks birthing / 16 weeks non-birthing).