Product Manager, Workload Connectivity

The posting, as Tailscale wrote it

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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 t

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• Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.
• Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
• Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
• A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.
• Paid parental leave program . We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness .