Shape workload connectivity at Tailscale with Kubernetes and cloud-native infrastructure expertise in a fully distributed, remote-first company.

As Product Manager, you will own Workload Connectivity strategy, roadmap, and business development. You will serve developers and platform engineers through Kubernetes tooling, CI/CD systems, containers, networking, and workload identity. The work spans product experience, integrations, pricing, packaging, and measurable adoption.

Key Responsibilities

Own vision, strategy, and roadmap for Workload Connectivity

Define developer experiences from authentication through troubleshooting

Drive Kubernetes operator roadmaps and cloud-native integrations

Develop pricing and packaging with cross-functional teams





Define adoption, activation, retention, and revenue metrics

Requirements

Seven-plus years in product management

Experience owning developer-facing infrastructure products

Fluency in Kubernetes, containers, networking, and automation

Experience building products for developers and platform engineers

Ability to lead products from strategy through measurable impact

Bring technical product leadership, commercial judgment, and customer insight to Tailscale’s workload connectivity strategy and growth.

📌 Workload Connectivity Product Manager (Winnipeg)
🏢 Tailscale
📍 Winnipeg