Senior New Biz Account Executive - Hybrid Toronto

Tailscale; Toronto; Hybrid; CAD 181,000 - 221,000; Full time

Benefits offered by this job

Remote-first environment

Equity and variable commission

Comprehensive benefits

Retirement contributions matching

Professional development funds

Job summary

Tailscale is seeking an ambitious New Business Account Executive to own the full sales cycle from prospecting to purchase. You will handle inbound leads, source a third of your own pipeline, and aim to earn customer trust at every step. The role is based in Toronto with hybrid work (3 days in-office).

You will engage with engineering leaders at innovative companies, travel to events when needed, and contribute to building a scalable sales playbook in a fast-growing startup environment.

Qualifications

• 2+ years of prospecting or closing experience in a door-to-door or in-person sales role.
• Ambition to build (and not just follow) a sales playbook.
• Technical background or curiosity in technology.
• Excellent communication and presentation skills.
• Proactive from lead to close and able to justify why you’re the best candidate.

Responsibilities

• Win new business by educating prospects about our services and helping them succeed with Tailscale.
• Experiment and move quickly by analyzing market landscapes and customer trends to inform campaigns.
• Travel to or organize local events and participate in industry events to evangelize Tailscale.
• Support customers across all time zones and manage activities, pipeline, and forecast in Gong and Salesforce.

Skills

Prospecting

Closing

Technical curiosity

Communication

Self-sourcing

Tools

Gong

Salesforce

Job description

Tailscale is seeking an ambitious New Business Account Executive to own the full sales cycle from prospecting to purchase. You will handle inbound leads, source a third of your own pipeline, and aim to earn customer trust at every step. The role is based in Toronto with hybrid work (3 days in-office).

You will engage with engineering leaders at innovative companies, travel to events when needed, and contribute to building a scalable sales playbook in a fast-growing startup environment.