Product Manager – Workload Connectivity

Tailscale

. Own Tailscale's Workload Connectivity product area and make it effortless for applications, services, and infrastructure to securely connect to required resources .

Posted 11/6/2026full-timeRemote • Canada, United StatesSeniorLead💰 CA$237,180 - CA$296,140 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in product management for developer-facing infrastructure, with a strong focus on Kubernetes, cloud-native technologies, and workload connectivity. Proven ability to define product strategy, drive adoption, and achieve measurable business impact through collaboration with cross-functional teams.

Highest-signal resume keywords

Product ManagementKubernetes ExpertiseCloud-Native InfrastructureDeveloper-Facing ProductsCommercial Judgment

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Product StrategyWorkload ConnectivityInfrastructure AutomationAPI DevelopmentMonitoring and TroubleshootingCloud PlatformsCI/CD SystemsWorkload IdentityNetworkingTechnical Writing

Soft Skills

CollaborationLeadershipCustomer InsightCross-Functional TeamworkProblem-Solving

Tools & Technologies

KubernetesTailscaleContainersDeveloper ToolingCloud Integrations

Industry Keywords

Workload AdoptionRevenue GrowthUsage-Based PricingDeveloper PlatformsOperational Experience

Tech Stack

Tools & technologies

CloudKubernetes

About the role

Key responsibilities & impact

Own Tailscale's Workload Connectivity product area and make it effortless for applications, services, and infrastructure to securely connect to required resources
Define product strategy across Kubernetes operators, ephemeral workloads, AI agent connectivity, cloud and infrastructure integrations, and Workload Connectivity monetization
Own the vision, strategy, and roadmap for Workload Connectivity
Define the end-to-end developer experience for workload authentication, deployment, monitoring, and troubleshooting
Drive the Kubernetes operator roadmap and establish reference architectures and integrations for cloud-native connectivity patterns
Partner with product, engineering, operations, and go-to-market teams on pricing, packaging, adoption, and revenue growth
Define and own success metrics for workload adoption, activation, retention, and revenue
Build customer insight by working directly with developers, platform engineers, and infrastructure teams
Collaborate across product teams on identity, access controls, networking, and developer tooling
Work with engineering, design, and go-to-market teams to make Tailscale the obvious choice for workload connectivity from first integration through production scale

Requirements

What you’ll need

7+ years in product management
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
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 and 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 have: experience with usage-based pricing for developer infrastructure products
Nice to have: hands-on Tailscale experience, particularly with Kubernetes or machine-to-machine connectivity
Nice to have: public technical writing, conference talks, or open-source contributions

Benefits

Comp & perks

An inclusive, flexible environment where you can be your authentic self
Competitive total compensation package including base salary, equity incentive plan, and variable commission for quota-based roles
Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for you and your family
Remote-first work environment with flexible work location and schedule
Virtual and in-person social events
Corporate co-working program through WeWork or similar spaces
Employer-funded retirement contributions matching employee contributions dollar-for-dollar, up to 0.75% of eligible compensation annually
Annual company retreat and team off-sites
$1500 USD annually for professional development
Mentorship, coaching, and internal promotion opportunities
Flexible paid time off program
Company-owned laptop choice of Mac or PC
Monthly home internet reimbursement
$500 USD home workstation customization allowance
Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents