# Principal Product Manager

**Company:** [Tailscale](https://hotfix.jobs/companies/tailscale)
**Location:** Remote
**Role:** Product Management
**Salary:** CA$264k – CA$330k/yr
**Experience:** 10+ years
**Skills:** Wireguard, Derp, Nat Traversal, Subnet Routing, DNS, Network Segmentation, BGP, Mpls, Ebpf, Ipsec, Openvpn, Kubernetes, Cli, Cloud Vpc Peering
**Posted:** 2026-08-05

> 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.

## Job Description

## 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.

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