Head of Commercial Expansion

Tailscale; Toronto; Hybrid; CAD 268,000 - 335,000; Full time

Benefits offered by this job

Remote first environment

Equity incentive plan

Variable commission for quota-based ro

Comprehensive benefits

Employer retirement contributions

Job summary

Tailscale is seeking a Sales Manager to lead Commercial Expansion Account Executives in Toronto, building a repeatable expansion motion and coaching a growing team.

You will drive expansion revenue, maintain a healthy pipeline, and forecast accurately while partnering with Customer Success, Marketing, Product, and Partnerships to grow adoption. This is a hybrid role with travel approximately quarterly and in‑office work in Toronto three days a week.

Qualifications

• At least 1 year of people management experience in a B2B SaaS sales environment.
• Proven ability to coach, develop, and motivate Account Executives or other quota‑carrying sales professionals.
• Strong understanding of the sales process, including prospecting, discovery, qualification, pipeline management, and closing.
• Experience driving team performance through data‑driven decision‑making, structured coaching, and clear accountability.
• Ability to thrive in a fast‑paced, high‑velocity sales environment while managing multiple priorities.
• Excellent written and verbal communication skills, with the ability to engage both technical and nontechnical stakeholders.
• A curious, proactive mindset with a bias for action and a passion for continuous improvement.
• Willingness to travel approximately once per quarter.
• Ability to work from our Toronto office three days per week.

Responsibilities

• Establish and lead Tailscale’s new Toronto sales hub, hire and onboard Commercial Expansion AEs, and foster a culture of curiosity and accountability.
• Drive expansion revenue, maintain a healthy pipeline, and deliver accurate forecasts.
• Prospect with reps, join customer conversations, and navigate fast‑moving expansions to larger deals.
• Translate call reviews and coaching sessions into practical development for reps.
• Create and refine a repeatable expansion playbook using data and customer insights.
• Collaborate with Customer Success, Marketing, Product, Sales Engineering, and Partnerships to grow adoption.

Skills

People management

Coaching & development

Data-driven decision making

Sales process knowledge

Team leadership

Customer-facing collaboration

Travel willingness

In-person collaboration

Job description

Tailscale is seeking a Sales Manager to lead Commercial Expansion Account Executives in Toronto, building a repeatable expansion motion and coaching a growing team.

You will drive expansion revenue, maintain a healthy pipeline, and forecast accurately while partnering with Customer Success, Marketing, Product, and Partnerships to grow adoption. This is a hybrid role with travel approximately quarterly and in‑office work in Toronto three days a week.