Build secure customer solutions as Tailscale’s Forward Deployed Engineer, applying networking, security, and troubleshooting expertise in a fully distributed company.

This customer-facing role bridges Tailscale’s technical capabilities with strategic customer needs. You will guide onboarding, drive adoption, provide technical support, and translate complex requirements into practical solutions. The role reports to the Team Lead, Customer Success Engineers, serving customers throughout their journey.

Key Responsibilities

Design custom integrations, tooling, and network architectures

Convert one-off solutions into reusable deployment frameworks

Lead strategic customer onboarding and provide training

Diagnose configuration, integration,



and platform issues

Conduct QBRs and identify deeper engagement opportunities

Requirements

Six-plus years in technical roles

At least two years of customer-facing experience

Enterprise consultative experience with customers

Understanding of networking, VPNs, security, and cloud infrastructure

Robust communication, troubleshooting, organizational, and collaborative skills

Apply customer success engineering, network architecture, and technical guidance to help strategic customers adopt Tailscale effectively.

📌 Forward Deployed Customer Success Engineer (Winnipeg)
🏢 Fdetimes
📍 Winnipeg