Job Overview
Location
Remote (Canada)
Job Type
Full-time
Category
Sales
Date Posted
May 14, 2026
Full Job Description
đź“‹ Description
- • As a Solutions Engineer - Commercial (Expansion Sales) at Tailscale, you will partner with Account Executives to drive new business for Commercial customers, co-owning a book of business and acting as a trusted technical advisor in complex sales cycles.
- • Day to day, you will lead technical discovery, design solution architectures, deliver demos and proof-of-concepts, guide multi-stakeholder deals, and provide structured feedback to influence product roadmap and go-to-market strategy.
- • Tailscale is a fully distributed, remote-first company building the new Internet by making secure device and network interconnection simple and safe for users ranging from hobbyists to multinational corporations, backed by top-tier venture capital.
- • In this role, you will deepen your expertise in zero-trust networking, cloud infrastructure, and enterprise sales while building scalable enablement resources and shaping the future of Tailscale’s product and GTM motion through direct customer impact.
🎯 Requirements
- • 4/5+ years in a customer-facing SE/SA role within networking or security software
- • Proven experience co-owning pipeline and influencing quota outcomes with Sales
- • Strong networking fundamentals (TCP/IP, DNS, routing, firewalls) and troubleshooting skills
- • Deep understanding of zero-trust networking, secure connectivity, and IAM integrations (SSO, SAML, OIDC)
- • Experience with infrastructure as code tools such as Terraform, Pulumi, Ansible, or CloudFormation
- • Hands-on architecture experience with AWS, GCP, and/or Azure
- • Excellent communication skills, capable of translating technical features into business value
- • Experience thriving in high-growth or startup environments
🏖️ Benefits
- • An inclusive, flexible environment where you can be your authentic self
- • A competitive total compensation package including base salary, equity, and variable commission
- • Comprehensive group benefits with no waiting period (health, vision, dental, and more)
- • Remote-first work model with access to corporate co-working spaces (e.g., WeWork)
- • $1500 USD annually for professional development, plus mentorship and coaching opportunities
- • Paid time off and healthy work-life integration with flexible PTO
- • Build-your-own home office setup: company-owned laptop, monthly internet reimbursement, and $1000 USD for workstation customization
- • Generous parental leave program with top-ups for up to 26 weeks from day one
Skills & Technologies
About Tailscale Inc.
Tailscale Inc. provides a zero-config virtual private network built on the open-source WireGuard protocol. It creates secure, encrypted mesh networks that connect devices, servers and users without traditional VPN hardware or complex firewall rules. The software runs on Linux, macOS, Windows, iOS, Android and container platforms, integrating with identity providers like Google Workspace, Microsoft Entra ID and Okta. Organizations use Tailscale to enable remote access to internal applications, SSH, RDP, databases and development environments, while maintaining centralized access controls and audit logs. The company is privately held and headquartered in Toronto, Canada.
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