About the role

Principal Product Manager leading Tailscale's secure networking dataplane. Setting connectivity, reliability, and infrastructure roadmaps for customers, enterprises, and cloud 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 operational primitives such as subnet routers, exit nodes, and Peer Relays
Own application-layer connectivity across App Connectors, Services, DNS, and network segmentation
Own the operator control surface across the admin console and CLI
Partner with the 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
Nice-to-have familiarity with VPN/tunneling protocols such as WireGuard, IPsec, and OpenVPN
Nice-to-have familiarity with low-level networking stacks such as kernel, eBPF, and userspace
Nice-to-have experience operating globally distributed infrastructure POPs, relays, and edge nodes
Nice-to-have familiarity with subnet routing, BGP, MPLS, cloud VPC peering, or data residency constraints
Nice-to-have application-layer connectivity experience with service mesh, API gateways, DNS, proxies/connectors, or network segmentation and policy
Nice-to-have experience building admin console and CLI control surfaces
Nice-to-have background in regulated industries
Nice-to-have public technical writing, conference talks, or open-source networking contributions
Nice-to-have hands-on experience with Tailscale at work or home

An inclusive, flexible environment where you can be your authentic self
A competitive total compensation package including equity incentive plan and variable commission for quota-based roles
Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for you and your family
Remote-first work environment
Virtual and in-person social events
Corporate co-working program
Employer-funded retirement contributions matching employee contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of eligible compensation
Annual company retreat and team off-sites
$1,500 USD annually for professional development
Mentorship, coaching, and internal promotion opportunities
Flexible paid time off
Company-owned laptop choice of Mac or PC
Monthly home internet reimbursement
$500 USD home office setup allowance
Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents