Product Manager, Workload Connectivity at Tailscale

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About Tailscale

Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

About the Role

We're hiring a Product Manager to own Tailscale's Workload Connectivity product area — making it effortless for applications, services, and infrastructure to securely connect to the resources they depend on.

Networks are increasingly made up of machines talking to machines. CI/CD pipelines, Kubernetes workloads, AI agents, and cloud services all need secure connectivity, often across environments and without human intervention. Tailscale provides the building blocks for these connections. Your job is to turn them into a cohesive product experience and a standalone line of business.

You'll own the product strategy across several key areas:

Kubernetes operator: Making Tailscale a natural part of Kubernetes infrastructure, enabling secure connectivity to and from clusters.
Ephemeral workloads: Enabling CI/CD runners, containers, and automated jobs to securely connect at scale.
Agent connectivity: Enabling AI agents to securely connect to the tools, services, and private infrastructure they need to operate.
Cloud and infrastructure integrations: Making Tailscale easy to deploy and operate within the cloud platforms and infrastructure tools developers already use.
Workload Connectivity as a business: Defining how machine-to-machine connectivity is packaged, measured, and monetized independently of traditional user-based VPN subscriptions.

You'll work closely with engineering, design, and go-to-market teams to make Tailscale the obvious choice for workload connectivity, from a developer's first integration to production deployments at scale.

Key Responsibilities

Own the vision, strategy, and roadmap for Workload Connectivity, including Kubernetes, ephemeral workloads, agent connectivity, and cloud integrations.
Define the end-to-end developer experience for connecting workloads, from authentication and deployment through monitoring and troubleshooting.
Drive the Kubernetes operator roadmap and establish reference architectures and integrations for common cloud-native connectivity patterns.
Partner with product, engineering, operations, and go-to-market teams to develop workload connectivity pricing and packaging, driving adoption and revenue growth.
Define and own success metrics for workload adoption, activation, retention, and revenue, using data to guide product investments.
Build deep customer insight by working directly with developers, platform engineers, and infrastructure teams.
Collaborate across product teams on shared foundations, including identity, access controls, networking, and developer tooling.

What We Are Looking For

7+ years in product management, with experience owning developer-facing infrastructure products such as cloud platforms, Kubernetes tooling, CI/CD systems, or developer platforms.
Strong technical fluency in cloud-native infrastructure, including Kubernetes, containers, networking, infrastructure automation, and workload identity.
Experience building products for developers and platform engineers, with a strong appreciation for APIs, documentation, and operational experience.
Demonstrated ability to own a product area end to end, from strategy and roadmap through launch, adoption, and measurable business impact.