Product Manager, Tailscale
Kubernetes
$177-221k
+ Equity
A zero config VPN for building secure networks
Be an early applicant
A zero config VPN for building secure networks
101-200 employees
Be an early applicant
$177-221k
+ Equity
101-200 employees
Company mission
To remove overhead and complexity from the “long tail” of software and operational problems that people face every day.
Role
Who you are
- 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
- 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
Desirable
- 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
What the job involves
- 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
Our take
The internet is a global phenomenon, but often online activity is unprotected which leaves users vulnerable to hackers on public networks. Additionally certain sites are inaccessible or censored depending on the users location. Use of a VPN enables a secure connection through an encrypted virtual tunnel which also disguises IP addresses. Traditional VPN's tunnel all network traffic through a central gateway server which can affect reliability, and VPN's almost always slow connection speed.
Tailscale is a VPN service built on top of a secure network fabric, which is unlike a traditional VPN provider as it ensures encrypted point-to-point connections by using the open source WireGuard protocol. Tailscale is configured, on average, in a matter of minutes, while other solutions take weeks to fully implement and then require several hours a week of maintenance.
The product has been well received with reviewers agreeing that it is easy to set up and a great tool for developers. The company plan to develop its product further by tackling the complexity of software and confront operational problems that people face daily. The company continues its expansion by empowering small teams to build systems that scale, without scaling overhead.
Steph
Company Specialist at Welcome to the Jungle
Insights
81% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Apr 2025
$160m
SERIES C
May 2022
$100m
SERIES B
Total funding: $275m
Company benefits
- Flexible (and reasonable) working hours—work/life balance is exceptionally important to us
- Competitive compensation, stock options and 401(k) (for United States-based employees)
- Comprehensive medical/dental/vision benefits, and more
- 4 weeks of paid vacation (standard across the company) + 12 company holidays per year
- An allowance for equipment to help you personalize your workspace
Company HQ
King West Village, Toronto, ON
Leadership
Avery Pennarun
(Co-Founder & CEO)A range of experience in software engineering including Senior Staff Software Engineer at Google Fiber. They co-founded EQL Data in 2009.
David Crawshaw
(Co-Founder & CTO)Previous experience includes working as a Staff Software Engineer at Google before co-founding Tailscale.
David Carney
(Co-Founder)Co-founded Format in 2012, working as a Full Stack Developer, COO and CFO. Also co-founded Form & Method and The Navarra Group.
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