Principal Product Manager
Leads the vision, roadmap, and customer-facing reliability strategy for Tailscale’s dataplane networking platform. Requires 10+ years of product management experience in networking or infrastructure and deep fluency across transport, overlay, and application-layer connectivity.
About the job
Responsibilities
- Set the vision and roadmap for the Tailscale 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 deployment requirements.
- Drive the roadmap for operational primitives such as subnet routers, exit nodes, and Peer Relays, including deployment topology, high-availability modes, route management UX, and production tooling.
- Own the application-layer connectivity surface, including App Connectors, Services, DNS, and network segmentation.
- Own the operator control surface used by network engineers and IT administrators to configure, segment, monitor, and troubleshoot networks at scale across the admin console and CLI.
- Partner with design to turn networking systems into clear, well-reasoned product surfaces.
- Own connectivity behavior across NAT types, operating systems, mobile carriers, enterprise firewalls, and challenging networks, improving success rates and customer debuggability.
- Partner with GTM, Customer Success, and Solutions Engineering on production traffic commitments, regulated deployments, and strategic enterprise deals.
- Represent the dataplane externally to enterprise customers, cloud partners, infrastructure vendors, and the networking community.
Requirements
- 10+ years of product management experience owning networking, transport, edge, or infrastructure products at scale.
- Experience with products such as CDNs, edge platforms, SD-WAN, overlay networks, cloud networking, service mesh, API gateways, DNS/traffic management, or identity-aware proxies.
- Deep networking fluency across routing, NAT traversal, MTU/MSS, congestion, latency, packet loss, overlay routing, proxies, connectors, DNS, and network segmentation.
- Ability to define performance commitments and customer-facing SLOs and operate under real production expectations.
Nice to Have
- Familiarity with VPN and tunneling protocols such as WireGuard, IPsec, or OpenVPN.
- Experience with kernel, eBPF, or userspace networking stacks.
- Experience operating globally distributed infrastructure POPs, relays, or edge nodes, including capacity planning and regional expansion.
- Familiarity with subnet routing, BGP, MPLS, cloud VPC peering, or data residency constraints.
- Experience with service mesh, API gateways, DNS, proxies/connectors, or network segmentation and policy.
- Experience building admin consoles and CLIs for configuring and troubleshooting networks at scale.
- Background in regulated industries such as finance, healthcare, or government.
- Public technical writing, conference talks, or open-source networking contributions.
- Hands-on experience with Tailscale.
Compensation and Benefits
- Base salary range: $263,980–$329,640 CAD.
- Equity incentive plan and variable commission for quota-based roles.
- Comprehensive health, vision, and dental benefits with no waiting period.
- Remote-first, flexible work environment with virtual and in-person social events and a corporate co-working program.
- Employer-funded retirement contributions matching employee contributions dollar-for-dollar, up to 0.75% of eligible compensation annually.
- Annual company retreat, team off-sites, and supported team travel.
- $1,500 USD annually for professional development.
Skills
Wireguard, Derp, Nat Traversal, Subnet Routing, DNS, Network Segmentation, BGP, Mpls, Ebpf, Ipsec, Openvpn, Kubernetes, Cli, Cloud Vpc Peering
Similar jobs
Product Management jobs
Headway
United States
Own the strategy and execution of Headway’s ML-powered patient-provider search, retrieval, and ranking systems. The role requires 10+ years of product management experience, shipped ranking or relevance systems, strong technical fluency in ML evaluation, and executive leadership.
Chime
San Francisco, CA
Leads the end-to-end acquisition and conversion strategy for Chime’s lending portfolio, spanning loans, credit cards, and lines of credit. Requires 11+ years of consumer product leadership and proven top-of-funnel lending experience with measurable growth, conversion, and CAC results.
Crusoe
San Francisco, CAOwn the multi-year vision, architecture, vendor strategy, and economics of Crusoe’s hyperscale storage foundation supporting AI workloads. The role requires 8+ years of technical product or infrastructure experience, deep storage expertise, and the ability to partner with senior engineering leadership.
Crusoe
Sunnyvale, CALeads the multi-year product vision, architecture, vendor strategy, and economics for Crusoe’s AI networking foundation. Requires 8+ years of technical product management or infrastructure engineering experience, deep networking expertise, and hands-on experience with RDMA and GPU cluster networking.
Headway
San Francisco, CAOwn the foundational data products that segment patients, measure cost of care, and translate outcomes into auditable payer-facing products. The role requires deep technical fluency, complex data infrastructure product ownership, and cross-functional leadership across engineering, clinical, and commercial teams.