Product Manager – Workload Connectivity

🔥 1 hour ago

🌐 Canada, United States – Remote

🇨🇦 Canada – Remote 🇺🇸 United States – Remote

💵 $237.2k - $296.1k / year

⏰ Full Time

🟠 Senior

🔴 Lead

✅ Product Manager

👻 Ghost score 20%

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Tailscale

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2020

☁️ SaaS

🔐 Security

📡 Telecommunications

💰 $100M Series B on 2022-05

SaaS • Security • Telecommunications

Tailscale is a company that provides a modern VPN solution founded on WireGuard technology, simplifying networking by creating secure, software-defined networks that connect users, services, and devices with ease. By eliminating the complexities of legacy VPNs, Tailscale offers secure remote access, site-to-site networking, and multi-cloud networking, all while ensuring user-friendly, quick deployment without complex configurations. Recognized for enabling zero-trust environments and seamless workflows, Tailscale supports robust security features such as automated user onboarding, encryption, and access control lists (ACLs). This tool is particularly popular for both enterprise and personal use, praised for its integration capabilities and ease of use, making secure networking accessible anywhere, regardless of infrastructure.

📋 Description

• 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

• 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

• 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

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