About the role

Principal Product Manager leading Tailscale's secure networking dataplane. Setting strategy for connectivity infrastructure serving millions of devices and critical enterprise workloads.

Responsibilities

Set the vision and roadmap for Tailscale's 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, including regional expansion, capacity planning, relay health observability, enterprise and private DERP/Peer Relay offerings, and sovereign or regulated deployments
Drive the roadmap for subnet routers, exit nodes, and Peer Relays, including deployment topology, high-availability modes, route management UX, and operational tooling
Own the application-layer connectivity surface covering App Connectors, Services, DNS, and network segmentation
Own the operator control surface across the admin console and CLI for configuring, segmenting, monitoring, and troubleshooting networks at scale
Partner with the embedded Network Features design lead on networking product surfaces
Own connectivity behavior across NAT types, operating systems, mobile carriers, enterprise firewalls, and unusual customer networks
Partner with GTM, Customer Success, and Solutions Engineering on production traffic commitments, regulated deployments, and strategic enterprise deals
Represent Tailscale's dataplane to enterprise customers, cloud partners, infrastructure vendors, and the networking community
Report directly to Tailscale's VP Product

10+ years in product management owning networking, transport, edge, or infrastructure products at scale
Deep networking fluency across routing, NAT traversal, MTU/MSS, congestion, latency, packet loss, overlay routing, proxies, connectors, DNS, and network segmentation
Ability to engage engineers across networking teams as a peer
Demonstrated ability to define performance commitments and customer-facing SLOs
Experience operating under real production expectations and handling missed commitments
Familiarity with VPN/tunneling protocols such as WireGuard, IPsec, or OpenVPN is nice to have
Familiarity with low-level networking stacks such as kernel, eBPF, or userspace is nice to have
Experience operating globally distributed infrastructure POPs, relays, and edge nodes is nice to have
Familiarity with subnet routing, BGP, MPLS, cloud VPC peering, or data residency constraints is nice to have
Experience with service mesh, API gateways, DNS, proxies/connectors, or network segmentation and policy is nice to have
Track record building admin console and CLI operator control surfaces is nice to have
Background in regulated industries is nice to have
Public technical writing, conference talks, or open-source networking contributions are nice to have
Hands-on experience with Tailscale at work or home is nice to have

Equity incentive plan
Variable commission for quota-based roles
Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for employees and families
Flexible remote-first work environment
Virtual and in-person social events
Corporate co-working program
Employer-funded retirement contributions matching contributions dollar-for-dollar, up to 0.75% of eligible compensation annually
Annual company retreat and team off-sites
Team travel and distributed collaboration
$1500 USD annually for professional development
Mentorship, coaching, and internal promotion opportunities
Flexible paid time off program
Company-owned laptop, with choice of Mac or PC
Monthly home internet reimbursement
$500 USD home office workstation customization allowance
Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents
Accessible and inclusive hiring process with accommodations available