Solutions Engineer - Commercial (Expansion Sales) Remote (Canada)

Tailscale; Canada; Remote; CAD 201,000 - 268,000; Full time

Benefits offered by this job

Inclusive environment

Equity plan

Group benefits

Remote-first

Retirement match

Team off-sites

Dev budget

PTO

Home office setup

Parental leave

Job summary

Tailscale is seeking a Commercial Solutions Engineer to partner with Sales in Canada, co-owning a book of business, leading technical discovery, and architecting secure solutions for Commercial customers.

You will drive demos, POCs, and multi-stakeholder deals, translating complex networking and IAM concepts into business value while shaping product direction. Remote-first with strong compensation and benefits across Canada.

Qualifications

• 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.
• 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.

Skills

Customer-facing SE

Sales quota influence

Networking fundamentals

Zero-trust networking

IAM integrations

AI gateway governance

PAM familiarity

Infrastructure as code

AWS/GCP/Azure

Clear communication

Tools

Terraform

Pulumi

Ansible

CloudFormation

AWS

GCP

Azure

Job description

Solutions Engineer - Commercial (Expansion Sales)

Remote (Canada)

Thank you for considering Tailscale. If this job description resonates with you, Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

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. 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

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. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

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.

CAN Pay Range (OTE)

$201,000 - $268,000 CAD

What We Offer

• An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
• A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
• 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). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
• 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.
• 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 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. 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 $500 USD to customize your workstation to make it your own.
• 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).

Tailscale is committed to providing an accessible and inclusive hiring process. 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. 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 .

Please note, you must reside in Canada to be considered for this position. We are not currently providing relocation support for this role. If you intended to apply for employment in another country where we are hiring, please return to our careers page and apply to the correct country’s job post for this role.

Please note, you must legally be able to work in Canada to be considered for this position. We are not currently able to provide immigration support for this role. If you intended to apply for employment in another country where we are hiring, please return to our careers page and apply to the correct country’s job post for this role.