Solutions Engineer - Commercial (Expansion Sales)Remote (Canada) We encourage you to help us break that statistic! 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. 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. About the RoleTailscale 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 robust sales acumen to win competitive deals, scale enablement, and influence product direction. 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. 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.Hands-on architecture experience with AWS, GCP, and/or Azure Excellent communication skills, capable of translating technical features into business value Tailscale's compensation package includes base salary, equity,



and comprehensive benefits. For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets. 201,000 - $268,000 CAD An inclusive, flexible environment where you can be your authentic self. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).

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).

Some roles require in-office collaboration depending on team needs, which will be clearly noted in the . Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.

Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United Kingdom, Singapore, and the United States. We support intentional in-person connectivity through team travel and distributed collaboration. Support for your personal and professional development.

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. Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter. Our hiring process uses AI-assisted tools to help screen and assess candidates. We are not currently providing relocation support for this role.

We are not currently able to provide immigration support for this role.

📌 Solutions Engineer - Commercial (Expansion Sales) Remote (Canada)
🏢 Tailscale
📍 Winnipeg