Vancouver Commercial Expansion Manager

WinsAbove; Vancouver; Hybrid; CAD 268,000 - 335,000; Full time

Benefits offered by this job

Inclusive, flexible environment

Base salary + equity + variable bonus

Comprehensive benefits

Remote‑first culture with occasional N

Job summary

Tailscale is building a Vancouver sales hub and seeks a thoughtful Sales Manager to lead Commercial Expansion AEs, growing existing customer relationships and navigating complex deals. You will coach reps, shape the expansion motion, and partner across Customer Success, Marketing, Product, and Sales Engineering.

As the first sales leader in Vancouver, you’ll hire, develop talent, and help scale a repeatable expansion strategy while contributing to a remote‑first culture with in‑office

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 Vancouver office three days per week

Responsibilities

• Help establish Tailscale’s new sales hub, hire and onboard Commercial Expansion AEs, and create a culture of curiosity, accountability, and shared success
• Drive expansion revenue, maintain a healthy pipeline, and deliver accurate forecasts
• Prospect alongside reps, join customer conversations, and help navigate pivotal deals - from fast‑moving expansions to larger, more complex opportunities
• Turn call reviews, role plays, and deal strategy sessions into practical coaching that sharpens skills and supports career growth
• Build and refine a repeatable expansion playbook, using sales data and customer insights to test approaches and scale what works
• Develop a deep understanding of Tailscale’s value and partner with Customer Success, Marketing, Product, Sales Engineering, and Partnerships to grow adoption

Skills

People management

Coaching

Sales leadership

B2B SaaS

Job description

Tailscale is building a Vancouver sales hub and seeks a thoughtful Sales Manager to lead Commercial Expansion AEs, growing existing customer relationships and navigating complex deals. You will coach reps, shape the expansion motion, and partner across Customer Success, Marketing, Product, and Sales Engineering.

As the first sales leader in Vancouver, you’ll hire, develop talent, and help scale a repeatable expansion strategy while contributing to a remote‑first culture with in‑office