Job Overview
Location
Remote (United States)
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 by co-owning a book of business, leading technical discovery, and acting as a trusted advisor to customers.
- • Day to day, you will partner with AEs to identify, qualify, and close new Commercial customer opportunities; lead technical discovery, solution architecture, demos, and POCs to accelerate decision-making; guide complex multi-stakeholder deals by aligning technical and business objectives; provide structured feedback to shape product roadmap and GTM strategy; and build scalable enablement resources, demo environments, and solution blueprints for the SE team.
- • Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. Founded in 2019 and fully distributed, the company is backed by Accel, CRV, Insight, Heavybit, and Uncork Capital, serving hobbyists to multinational corporations who use Tailscale daily to protect networks and share access to internal tools.
- • In this role, you can learn to influence product direction and GTM strategy through structured feedback, deepen your expertise in zero-trust networking and cloud architectures, and grow your impact in a high-growth startup environment while developing scalable enablement resources that elevate the entire SE team’s effectiveness.
🎯 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 incentive plan, and variable commission
- • Comprehensive group benefits with no waiting period (health, vision, dental, and more)
- • Remote first company culture with access to corporate co-working program (WeWork or similar)
- • $1500 USD annually for professional development, plus mentorship, coaching, and internal promotion opportunities
- • Paid time off and healthy work-life integration with flexible PTO
- • Build-your-own home office setup: company-owned laptop (Mac or PC), monthly home internet reimbursement, and $1000 USD to customize workstation
- • Generous parental leave program from day one with top-ups for up to 26 weeks
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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