Tailscale

Tailscale

Principal Product Manager (Dataplane)

Remote (Canada) · Principal

Sponsorship not specified$264k-$330kDetected 5 days ago
Cloud PlatformsKubernetesCI/CDAgentic AIStatisticsProduct ManagementProduct StrategyCustomer SuccessDNSFirewallVPNBGP/OSPFSD-WANCollaborationMentoringWriting

About the role

  • From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more.
  • See How Tailscale Works and How NAT Traversal Works to learn more.
  • Tailscale's growth has significantly expanded the scope and importance of the dataplane.

Responsibilities

  • Own the application-layer connectivity surface - App Connectors, Services, DNS, and network segmentation - that determines how traffic finds its destination and how AI agents, CI/CD, and Kubernetes workloads reach the SaaS and cloud resources they depend on
  • Own the operator control surface: how network engineers and IT admins configure, segment, monitor, and troubleshoot their networks at scale, across both the admin console and the CLI
  • Partner closely with the embedded Network Features design lead to turn abstract networking systems into legible, well-reasoned product surfaces
  • Partner with GTM, Customer Success, and Solutions Engineering on production traffic commitments, regulated deployments, and strategic enterprise deals, turning customer learnings into roadmap priorities
  • We support intentional in-person connection through team travel and distributed collaboration.
  • Support for your personal and professional development.

Requirements

  • Demonstrated ability to define performance commitments and customer-facing SLOs, operate under real production expectations, and handle the moments when systems miss those commitments

Nice to have

  • Familiarity with VPN/tunneling protocols (WireGuard, IPsec, OpenVPN) or low-level networking stacks (kernel, eBPF, userspace)
  • Experience operating globally distributed infrastructure POPs, relays, and edge nodes including capacity planning, regional expansion, and the customer-visible performance tradeoffs that come with it
  • Familiarity with subnet routing, BGP, MPLS, cloud VPC peering, or data residency constraints
  • Experience with application-layer connectivity: service mesh, API gateways, DNS, proxies/connectors, or network segmentation and policy
  • Public technical writing, conference talks, or open-source networking contributions
  • Hands-on experience with Tailscale at work or home
  • Individual offers may vary based on experience and skill set.
  • $263,980 - $329,640 CAD

Skills

  • About Tailscale

Compensation

  • Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore.
  • Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.

Benefits

  • An inclusive, flexible environment where you can be your authentic self.
  • This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
  • Comprehensive group benefits with no waiting period.
  • Take advantage of coverage for health, vision, dental, and more for you and your family!
  • Employer-funded retirement contributions.
  • Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
  • Paid time off and a healthy work-life integration.
  • Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
  • A build-your-own home office setup.
  • You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.
  • Paid parental leave program.
  • We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Company info

  • Drive the roadmap for the operational primitives customers use such as subnet routers, exit nodes, and Peer Relays including deployment topology, high-availability modes, route management UX, and production operational tooling
  • Own connectivity behavior across the full matrix of NAT types, operating systems, mobile carriers, enterprise firewalls, and the "weird" networks customers actually run, improving both success rates and customer debuggability
  • Represent Tailscale's dataplane externally to enterprise customers, cloud partners, infrastructure vendors, and the networking community as a credible domain authority
  • What We Are Looking For

Equal opportunity

  • If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.
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This listing is sourced directly from Tailscale's careers page and normalized into a canonical job model.