SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Salary: CAD 201,000 - 201,000 / annual
Tailscale is a secure networking platform built on WireGuard that helps teams and organizations securely interconnect people and devices. The company was founded in 2019 and is backed by top-tier VCs including Accel, CRV, and Insight. With 100,000+ monthly active users and a vibrant community, Tailscale is rapidly growing in the enterprise security space.
This Senior Account Executive role is part of the New Business team and focuses on hunting and closing new customer accounts. Unlike a pure farming role, you'll receive inbound leads via round robin but are expected to source approximately one-third of your own pipeline through prospecting. You'll own the complete sales cycle from initial prospect contact through purchase, building customer trust at every stage.
Key responsibilities include:
- Identifying and reaching the right stakeholders at prospective customers
- Educating prospects about Tailscale's services and driving adoption
- Analyzing market landscapes and customer trends to inform sales campaigns
- Attending and organizing local and industry events to evangelize the product
- Supporting customers across multiple time zones
- Managing pipeline, activities, and forecasts in Gong and Salesforce
You should have 2+ years of prospecting or closing experience in door-to-door or in-person sales environments. A technical background or genuine curiosity about technology is essential, as you'll be selling to senior technical buyers (VP Engineering, CTO, Head of Platform, CISO). Strong communication and presentation skills are required. The role values proactive candidates who can self-source opportunities and guide customers from discovery through closed deals. The posting encourages candidates to go beyond standard application processes and directly prospect the hiring manager.
This is a hybrid role based in Vancouver requiring 3 days per week in-office. Tailscale offers competitive compensation including base salary, equity, and comprehensive benefits with no waiting period.
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
