Solutions Engineer - Commercial (Expansion Sales)

About Tailscale

Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. We're building a future for the Internet that's easy, sensible, and safe. 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.
• Familiarity with privileged access management (PAM) tools (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.

What We Offer

• Competitive Compensation: Base salary, equity incentive plan, and variable commission.
• Comprehensive Benefits: Health, vision, dental, and more with no waiting period.
• Remote-First Culture: Work from anywhere with a monthly internet reimbursement and a $500 home office stipend.
• Professional Development: $1,500 USD annually for growth, mentorship, and coaching.
• Work-Life Balance: Flexible paid time off and generous parental leave (20 weeks for birthing parents, 16 weeks for non-birthing).
• Retirement: Employer-funded retirement contributions (up to 0.75% match).
• Connection: Annual company retreats, team off-sites, and corporate co-working program access.