237K–296K CAD / year
Product Manager, Workload Connectivity
ProductRemote — Canada, United States, United Kingdom, Singapore
Published on 2026-11-06
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About this role
Own the strategy and roadmap for Tailscale’s Workload Connectivity product area, helping applications, services, and infrastructure connect securely. Shape the developer experience and build workload connectivity into a distinct business, including its packaging, measurement, and monetization.
About the company
Tailscale builds a zero-config mesh VPN on WireGuard so teams can securely connect devices, servers, and cloud resources without traditional VPN complexity.
The team
Workload Connectivity
Stack
KubernetescontainersCI/CDcloud infrastructure
What you'll do
- Own the vision, strategy, and roadmap across Kubernetes, ephemeral workloads, agent connectivity, and cloud integrations.
- Define the end-to-end developer experience for workload authentication, deployment, monitoring, and troubleshooting.
- Drive the Kubernetes operator roadmap and develop reference architectures and integrations.
- Partner with cross-functional teams on pricing, packaging, adoption, and revenue growth.
- Set and track workload adoption, activation, retention, and revenue metrics.
- Gather customer insights from developers, platform engineers, and infrastructure teams.
- Collaborate on shared identity, access control, networking, and developer tooling foundations.
What we're looking for
- 7+ years of product management experience owning developer-facing infrastructure products.
- Strong technical fluency in cloud-native infrastructure, Kubernetes, containers, networking, infrastructure automation, and workload identity.
- Experience building products for developers and platform engineers, including APIs, documentation, and operational experience.
- Ability to own a product area from strategy through launch, adoption, and measurable business impact.
- Strong commercial judgment and experience turning technical capabilities into sustainable revenue.
- Ability to work with sophisticated technical customers and lead cross-functional teams through ambiguity.
Nice to have
- Experience with usage-based pricing for developer infrastructure products.
- Hands-on Tailscale experience, particularly with Kubernetes or machine-to-machine connectivity.
- Public technical writing, conference talks, or open-source contributions.
Benefits
- Equity incentive plan.
- Remote-first work, with a corporate coworking program and supported team travel.
- Employer retirement contributions matching up to 0.75% of eligible compensation.
- $1,500 USD annual professional development budget.
- Flexible paid time off.
- $500 USD home-office setup allowance and monthly internet reimbursement.
- Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents.
- Health, vision, and dental coverage with no waiting period.