At a Glance
- Tasks: Partner with sales to drive new business and lead technical solutions.
- Company: Join Tailscale, a remote-first tech company focused on secure connectivity.
- Benefits: Competitive salary, equity, health benefits, and flexible work environment.
- Other info: Enjoy professional development support and a vibrant team culture.
- Why this job: Make an impact in a growing company while working with cutting-edge technology.
- Qualifications: 4+ years in customer-facing roles with networking or security software experience.
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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.
Compensation and 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. 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.
- A competitive total compensation package, including a base salary, an equity incentive plan and variable commission (for quota-based roles).
- Comprehensive group benefits with no waiting period, covering health, vision, dental, and more for you and your family.
- Remote first company — most of our teams work fully remotely.
- Employer-funded retirement contributions, matching your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
- Support for your personal and professional development with $1500 USD annually for professional development.
- Paid time off and a healthy work-life integration.
- A build-your-own home office setup with a company-owned laptop (Mac or PC), monthly home internet reimbursement, and $500 USD to customize your workstation.
- Paid parental leave program with top-ups for birthing and 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.
Please note, you must reside in Canada to be considered for this position. We are not currently providing relocation support for this role.
Solutions Engineer – Remote in Winnipeg employer: Tailscale
Tailscale is an exceptional employer that fosters a fully remote, inclusive work culture where employees can thrive both personally and professionally. With a competitive compensation package, comprehensive benefits, and a strong emphasis on employee growth through mentorship and professional development funding, Tailscale empowers its team to integrate work and life seamlessly while contributing to meaningful projects that enhance internet security for users worldwide.
