Product Manager, Workload Connectivity

Tailscale

2h • $177,000 - $221,000 • Remote

About The Position

Tailscale is hiring a Product Manager to own its Workload Connectivity product area, making it easy for applications, services, and infrastructure to securely connect to the resources they depend on. The role covers machine-to-machine connectivity across CI/CD pipelines, Kubernetes workloads, AI agents, and cloud services, turning Tailscale’s connectivity building blocks into a cohesive product experience and a standalone line of business.

The Product Manager will own strategy across the Kubernetes operator, ephemeral workloads, agent connectivity, and cloud and infrastructure integrations. They will define how Workload Connectivity is packaged, measured, and monetized independently of traditional user-based VPN subscriptions, and partner with engineering, design, and go-to-market teams to make it a compelling option from first integration through production at scale.

Requirements

• 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.

Nice To Haves

• 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.

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.

Benefits

• Competitive total compensation package, including base salary, an equity incentive plan, and variable commission for quota-based roles.
• Comprehensive group benefits covering health, vision, dental, and more for employees and their families, with no waiting period.
• Employer-funded retirement contributions with dollar-for-dollar matching up to a maximum annual employer contribution equal to 0.75% of eligible compensation.
• Annual company retreat, team off-sites, and supported team travel for in-person connection.
• $1,500 USD annually for professional development, with mentorship, coaching, and internal promotion opportunities also available.
• Flexible paid time off.
• Company-owned laptop (Mac or PC), monthly home internet reimbursement, and $500 USD to customize a home workstation.
• Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed