Tailscale

Product Manager - Kubernetes

Canada

Not SpecifiedCompensation
Expert & Leadership (9+ years)Experience Level
Full TimeJob Type
UnknownVisa
Internet Software & ServicesIndustries

Staff Product Manager, Machine-to-Machine & Kubernetes

About Tailscale

Tailscale is building the new Internet 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.


Position Overview

We’re seeking an experienced Staff Product Manager to lead our strategic machine-to-machine (M2M) initiatives, with a specific emphasis on Kubernetes integration. Reporting directly to the Head of Product, you'll play a critical role in shaping our M2M product strategy and roadmap during a pivotal growth phase.

You’ll own the vision, strategy, and execution for Tailscale’s Kubernetes-native solutions and broader machine-to-machine capabilities. Collaborating closely with engineering leadership, design, security teams, and senior stakeholders, you'll build innovative solutions to simplify secure connectivity and automation for enterprise customers. You'll also identify new market opportunities and craft winning strategies to expand Tailscale’s presence and success in machine-to-machine and Kubernetes ecosystems.

A deep curiosity and passion for creating exceptional developer experiences is essential, ensuring that Tailscale remains intuitive, powerful, and delightful for technical users.


Key Responsibilities

  • Define and drive strategic initiatives around machine-to-machine communication, Kubernetes integrations, workload identity, and automation capabilities.
  • Identify emerging market opportunities and develop strategic approaches to effectively capture them.
  • Collaborate with engineering, design, and cross-functional teams to develop Kubernetes-native features and services.
  • Engage regularly with enterprise customers, translating their M2M and Kubernetes requirements into clear product strategies and actionable roadmaps.
  • Provide thought leadership internally and externally around Kubernetes ecosystems and best practices.
  • Mentor and elevate the broader product management team, fostering a culture of technical excellence and collaborative product development.

What We Are Looking For

  • 7+ years of product management experience, ideally focused on Kubernetes, automation, or infrastructure products.
  • Deep expertise in Kubernetes ecosystems, CNCF projects, and developer tools.
  • Familiarity and experience with service mesh technologies, such as Istio, Linkerd, or similar tools.
  • Proven ability to lead strategic, complex technical initiatives at enterprise scale.
  • Exceptional strategic thinking, market analysis, and ability to identify new opportunities and create winning strategies.
  • Deep curiosity and passion for building exceptional developer experiences.
  • Excellent communication and problem-solving abilities, comfortable navigating technical complexity and ambiguity.
  • Demonstrated ability to effectively collaborate with executives, engineering leaders, and cross-functional stakeholders.

Nice to Have

  • Hands-on experience with Tailscale at work or home.
  • Experience with secure networking, identity management, Zero Trust architectures, or related enterprise security products.
  • Familiarity with infrastructure-as-code (IaC) and GitOps practices.
  • Direct experience with regulated industries such as finance, healthcare, or government.

Compensation and Benefits

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.

Salary Range: $237,180 - $296,140 CAD


Employment Type:

Location Type:

Skills

Kubernetes
Machine-to-Machine Communication
Workload Identity
Automation
Product Strategy
Developer Experience
Security
Cross-functional Collaboration

Tailscale

Secure VPN for remote resource access

About Tailscale

Tailscale offers a secure networking solution that allows users to access remote resources like virtual machines and databases from anywhere using a WireGuard-based Virtual Private Network (VPN). Its service is designed for businesses and individuals needing to manage private resources remotely, with a focus on simplicity and minimal setup. Tailscale's freemium model attracts a wide user base, allowing users to start for free and upgrade for additional features. The company aims to enhance data security while providing an easy-to-use remote access solution.

None, CanadaHeadquarters
2019Year Founded
$111.9MTotal Funding
SERIES_BCompany Stage
Enterprise Software, CybersecurityIndustries
51-200Employees

Benefits

Health Insurance
Dental Insurance
Vision Insurance
Flexible Work Hours
Remote Work Options
Unlimited Paid Time Off
Parental Leave
Professional Development Budget
Home Office Stipend
Phone/Internet Stipend
Company Equity

Risks

A critical vulnerability in Windows client poses remote code execution risk.
Cooling venture funding may impact Tailscale's future investment opportunities.
Scalability challenges may arise with rapid enterprise adoption of zero-trust solutions.

Differentiation

Tailscale uses WireGuard's Noise protocol for trusted encryption standards.
It integrates with existing identity providers like GSuite and Office365 for easy setup.
Tailscale offers over 100 integrations, fitting into almost any tech stack.

Upsides

Tailscale's zero-trust solution meets growing demand for enterprise security.
The $100 million Series B funding boosts product expansion and market reach.
Integration with Mullvad enhances privacy with a global VPN server network.

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