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.

Job Description

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

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 Ranges

$237,180—$296,140 CAD

Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

What We Offer

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.
Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team/department off-sites, or use your individual travel budget to meet up with team members in Canada, the US, or the UK.
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 $1000 USD to customize your workstation to make it your own.
Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.

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 https://tailscale.com/scam-awareness.

Product Manager - Kubernetes

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