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Salary: CAD 201,000 - 201,000 / annual
Tailscale is a secure networking platform built on WireGuard that makes safe connection effortless. The company helps teams of all sizes—from hobbyists to multinational corporations—securely interconnect people and devices, protect networks, and share access to internal tools. Founded in 2019 and fully distributed, Tailscale is backed by top-tier VCs including Accel, CRV, Insight, Heavybit, and Uncork Capital.
You will join the New Business Account Executive team as an ambitious seller responsible for owning the full sales cycle from prospect to purchase. This is not a "farmer" role—you will receive inbound leads via round robin but must also source and prospect a third of your own pipeline. You'll build customer trust at every step and work with a vibrant community of 100,000+ monthly active users, many of whom are engineering leaders at innovative companies.
Key responsibilities include:
- Winning new business by finding the right contacts at prospective customers, educating them about Tailscale's services, and supporting their success
- Experimenting and moving quickly by analyzing market landscapes and customer trends to inform sales campaigns
- Traveling to or organizing local events and attending large industry events to evangelize Tailscale
- Supporting customers across all time zones
- Managing activities, pipeline, and forecasts in Gong and Salesforce
This role is based in Toronto and requires hybrid work (3 days per week in-office). You will be part of a remote-first company with intentional in-person collaboration through team off-sites and an annual company retreat.
REQUIREMENTS:
- 2+ years of prospecting or closing experience in a door-to-door or in-person sales role
- Ambition to build (not just follow) a sales playbook
- Technical background or strong curiosity in technology
- Excellent communication and presentation skills
- Experience self-sourcing opportunities and guiding customers from discovery through closed-won deals with senior technical buyers (VP Engineering, CTO, Head of Platform, CISO)
- Proactive approach: the posting encourages candidates to go beyond applying on the website—find the hiring manager, prospect thoughtfully, and explain why you're the best fit
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
