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Forward Deployed Engineer

Tailscale· Customer Success
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RemoteCA$201k - CA$335kfull-timePosted 2mo ago

About the role

Forward Deployed Engineer at Tailscale who partners with strategic customers to onboard, adopt, and optimize use of Tailscale products, blending technical delivery with customer success and advocacy.

Responsibilities

  • Design and build novel solutions to complex customer challenges that fall outside Tailscale’s standard deployment patterns (e.g., prototyping custom integrations, tooling, and network architecture; using structured experimentation and testing to validate solutions for bespoke client uses)
  • Turn one-off customer solutions into repeatable, reusable assets such as reference architectures, deployment frameworks, and tooling
  • Lead and manage the onboarding process for new strategic customers, providing training and resources for long-term success
  • Offer technical support for customers, diagnosing and resolving issues across Tailscale's platform
  • Conduct QBRs with customers to review usage, success metrics, and future goals
  • Build strong relationships with customers, acting as a trusted advisor and providing best practices and recommendations
  • Serve as the voice of the customer to product and engineering teams to drive improvements
  • Work with sales, product, engineering, and support teams to ensure smooth handoffs and escalations
  • Develop and maintain technical documentation, FAQs, and guides for customer self-serve and internal sharing

Qualifications

  • 6+ Years in a technical role with minimum 2 years of customer-facing experience (Solutions engineer/architect, Sr. Support Engineer, etc.)
  • Experience with enterprise customers in a consultative capacity
  • Strong understanding of networking, VPNs, and security principles; experience with cloud infrastructure (AWS, GCP, Azure) and tools like Docker, Kubernetes, and other DevOps technologies
  • Prior experience in a customer-facing technical role such as Technical Support Engineer, Solutions Engineer/architect, or Customer Success Engineer at a SaaS company
  • Ability to clearly explain complex technical concepts to diverse audiences; strong written and verbal communication skills
  • Analytical mindset and troubleshooting skills with methodical problem-solving ability
  • Passion for delivering excellent customer service and building long-term relationships
  • Ability to manage multiple accounts, prioritize tasks, and maintain project momentum
  • Collaborative mindset and ability to work cross-functionally with product, sales, and engineering teams

Skills

Required:Customer-facing communicationNetworkingCloud infrastructureContainers and orchestration

Benefits

  • An inclusive, flexible environment
  • Competitive total compensation package (base salary, equity, variable compensation)
  • Comprehensive group benefits (health, vision, dental, and more)
  • Remote first company with optional in-person collaboration depending on team needs
  • Employer-funded retirement contributions (matching up to 0.75% of eligible compensation)
  • Opportunity to connect with other employees in Canada, the US, UK, and Singapore
  • Professional development support (USD 1500 annually)
  • Paid time off and flexible PTO program
  • Build-your-own home office setup (company laptop choice, internet reimbursement, $500 USD to customize workstation)
  • Paid parental leave program (20 weeks birthing, 16 weeks non-birthing)
Last updated Oct 22, 2026. Interested? Apply on the company site.

About Tailscale

Secure Connectivity for AI, IoT & Multi-Cloud

The connectivity platform for devs, IT, and security teams. Zero Trust identity-based access that deploys in minutes and scales to every resource.

SecurityNetworkingZero TrustIdentity-based accessMulti-Cloud
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