Product Manager, Workload Connectivity at Tailscale (Canada)Product Manager, Workload Connectivity

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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.

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.

• 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.

• 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.

• 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.

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set. CAN Pay Range $237,180—$296,140 CAD

• An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
• A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
• Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
• 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 tailscale.com/scam-awareness.