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Tailscale Inc.
Solutions Engineer - Commercial (Expansion Sales) Remote (Canada)Tailscale Inc. • Winnipeg, Canada
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Solutions Engineer - Commercial (Expansion Sales) Remote (Canada)

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

Tailscale Inc. • Winnipeg, Canada
8 days ago
Salary
CA$201,000.00 yearly
Job type
  • Full-time
  • Remote
Job description
Solutions Engineer - Commercial (Expansion Sales) Remote (Canada)

About Tailscale Tailscale is building the new Internet 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.

Job Description 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 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

Benefits

An inclusive, flexible environment where you can be your authentic self.

A competitive total compensation package.

Comprehensive group benefits with no waiting period.

Remote first company – most teams work fully remotely.

Opportunity for in‑person connection through retreats, off‑sites, and team travel.

Support for personal and professional development.

Paid time off and a healthy work‑life integration.

A build‑your‑own home office setup.

Generous parental leave program from your first day.

Equal Employment Opportunity As set forth in Tailscale’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Location Requirement You must reside in Canada to be considered for this position. We are not currently able to provide relocation or immigration support.

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Solutions Engineer - Commercial (Expansion Sales) Remote (Canada) • Winnipeg, Canada

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