Commercial Solutions Engineer - Networking & Security

About Tailscale

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. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

About the Role

Tailscale is seeking an experienced Commercial Solutions Engineer to partner with Sales in driving new business for Commercial customers. You will co-own a book of business with Account Executives, lead technical discovery and architecture design, and act as a trusted advisor to customers. This role blends deep networking and security expertise with strong sales acumen to win competitive deals, scale enablement, and influence product direction.

Key Responsibilities

• 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, aligning technical and business objectives.
• Provide structured feedback to shape product roadmap and GTM strategy.
• Build scalable enablement resources, demo environments, and solution blueprints for the SE team.

What We Are Looking For

• 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)
• Understanding of AI gateway and governance platforms for centralized LLM access, usage visibility, and audit
• Familiarity with privileged access management (PAM) including session recording, just-in-time access, and protocol-aware controls (e.g., Border0, CyberArk, Teleport)
• 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

Compensation & Benefits

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits.

CAN Pay Range (OTE): $201,000 - $268,000 CAD

What We Offer:

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package (base salary, equity, variable commission).
• Comprehensive group benefits with no waiting period (health, vision, dental, etc.).
• Remote-first company with flexibility for virtual and in-person events.
• Opportunities for in-person connection through company retreats and team off-sites.
• Support for personal and professional development ($1500 USD annually).
• Generous paid time off and a healthy work-life integration.
• A build-your-own home office setup (laptop, internet reimbursement, workstation stipend).
• Generous parental leave program (up to 26 weeks).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation, please contact your recruiter.
Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.
Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.