[Hiring] Product Manager @Tailscale

Role Description

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.

• 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.

Qualifications

• 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.
• Strong commercial judgment, with the ability to turn technical capabilities into differentiated products and sustainable revenue.
• Ability to work directly with sophisticated technical customers and lead cross-functional teams through ambiguity.

Requirements

• 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

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package, including base salary, equity incentive plan, and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period, covering health, vision, dental, and more for you and your family.
• Remote first company — most of our teams work fully remotely.
• Employer-funded retirement contributions, matching dollar-for-dollar up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• Connect with other Tailscalars IRL through annual company retreats and team off-sites.
• Support for your personal and professional development with $1500 USD annually for professional development.
• Flexible, paid time off program supporting any situation life throws your way.
• A build-your-own home office setup with a company-owned laptop, monthly home internet reimbursement, and $500 USD for workstation customization.
• Paid parental leave program with top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).