Solutions Engineer - Commercial (Expansion Sales)

Tailscale

7d • CA$201,000 - CA$268,000 • Remote

About The Position

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.

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)
• 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

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.

Benefits

• Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
• Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you).
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
• Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
• Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
• A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own.
• Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed