Key Responsibilities

• Own the vision, strategy, and roadmap for Tailscale's networking features: App Connectors, DNS, Funnel, and Tailscale Services
• Own the operator experience across these surfaces: how network engineers and IT admins configure, segment, monitor, and troubleshoot them at scale, in both the admin console and the CLI
• Partner with GTM, Customer Success, and Solutions Engineering on production commitments and strategic deals, and champion the migration path from reverse proxies, bastion hosts, cloud ingress, and service meshes to Tailscale
• Build systematic customer insight across the full spread of Tailscale users, from a homelab operator exposing a media server through Funnel to a large enterprise replacing its service registry

What We Are Looking For

• 7+ years in product management, including direct ownership of an application-layer connectivity product: reverse proxies, ingress controllers or gateways, API gateways, service mesh or service registry, DNS and traffic management, secure tunneling and exposure products, or identity-aware proxy connectors
• A track record of turning a complex networking system into a legible product surface: you can point to an object model, a set of defaults, or a configuration experience you designed and explain why it was right
• End-to-end ownership of a product area: strategy, requirements, launch (docs, enablement, rollout), and the iteration after launch
• Evidence of data-informed decisions — metrics you defined, instrumentation you pushed for, and at least one time the data changed your mind

Nice To Have

• Experience with Product Led Growth and how to balance that with enterprise buying motions
• Kubernetes networking: ingress, Gateway API, operators, or service exposure patterns
• Hands-on experience with secure tunneling and exposure products (ngrok, Cloudflare Tunnel, Cloudflare Access, Teleport, Zscaler Private Access) as a builder or a heavy user
• Abuse prevention, rate limiting, or trust and safety work on a publicly exposed service
• Familiarity with VPN and tunneling protocols (WireGuard, IPsec), BGP, cloud VPC peering, or PrivateLink-style private connectivity
• Public technical writing, conference talks, or open-source contributions in networking
• Hands-on experience with Tailscale at work or at home

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.

US Pay Range

$177,000

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$221,000 USD

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.
• Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.
  
• 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 $500 USD to customize your workstation to make it your own.
• Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

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.