Tailscale
Tailscale
51 – 200 Employees
SaaSSecurityTelecommunications
Tailscale builds secure networking software that connects people, services, and devices across locations and cloud environments. Its modern VPN is based on WireGuard and is designed to replace the complexity of traditional VPN infrastructure with fast deployment, encrypted connections, access controls, and zero-trust networking capabilities. The company operates across SaaS, security, and telecommunications, supporting use cases such as remote access, site-to-site connectivity, and multi-cloud networking for both organizations and individual users.

Infrastructure Engineer, Tailscale (Remote, United States)

Build and operate scalable, observable cloud infrastructure for Tailscale’s secure networking software. Support internal teams with CI/CD, Kubernetes, infrastructure as code, and incident response.

Description

  • Provide shared engineering services to internal business units.
  • Create tools and processes that help internal teams work effectively.
  • Build stakeholder relationships and lead projects from start to finish.
  • Partner with customer-facing teams to improve their daily operations.
  • Work with product engineering to gather data for business decisions.
  • Strengthen observability through metrics, alerting, logging, and telemetry.
  • Identify and implement improvements to continuous deployment.
  • Manage cloud infrastructure using infrastructure as code.
  • Partner with engineering teams on infrastructure improvements across functions.
  • Automate upgrades for managed services and virtual machines.
  • Design, build, test, and document core software components.
  • Operate services through monitoring, incident response, and customer support escalations.
  • Analyze and improve system efficiency, scalability, and stability.

Requirements

  • Hands-on experience with CI/CD, secrets management, infrastructure as code, and observability.
  • Experience with distributed systems.
  • Experience operating managed services in a cloud environment; AWS experience is preferred.
  • Production Kubernetes experience is a strong plus.
  • Familiarity with networking concepts, including IP addressing and routing.
  • Go experience is a plus.
  • Ability to give and receive constructive feedback and work independently.
  • Flexibility to adapt to the changing needs of a startup.
  • Strong written and verbal communication skills.

Benefits

  • An inclusive, flexible workplace where employees can be themselves.
  • Competitive total compensation, including base salary, equity incentives, and variable commission for quota-based roles.
  • Comprehensive group health, vision, dental, and other benefits for employees and their families, with no waiting period.
  • Remote-first work with flexibility in work location and schedule.
  • Virtual and in-person social events.
  • Corporate co-working program.
  • Employer retirement contributions match employee contributions dollar-for-dollar, up to an annual employer contribution of 0.75% of eligible compensation.
  • Annual company retreat and team off-sites.
  • $1,500 USD per year for professional development.
  • Mentorship, coaching, and opportunities for internal promotion.
  • Flexible paid time off.
  • Company-provided laptop, Mac or PC.
  • Monthly home internet reimbursement.
  • $500 USD allowance for home office or workstation customization.
  • Paid parental leave top-ups of 20 weeks for birthing parents and 16 weeks for non-birthing parents.
  • Accessible, inclusive hiring process with accommodations available.

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