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 ConnectivityDefine developer experiences from authentication through troubleshootingDrive Kubernetes operator roadmaps and cloud-native integrationsDevelop pricing and packaging with cross-functional teamsDefine adoption, activation, retention, and revenue metricsRequirements:

Seven-plus years in product managementExperience owning developer-facing infrastructure productsFluency in Kubernetes, containers, networking, and automationExperience building products for developers and platform engineersAbility to lead products from strategy through measurable impactBring technical product leadership, commercial judgment, and customer insight to Tailscale’s workload connectivity strategy and growth.

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