Manager, Commercial Expansion

About this role

Lead and develop a team of Commercial Account Executives focused on expanding existing customer relationships. As Tailscale’s first sales leader in Vancouver, establish the local sales hub and build a repeatable expansion sales motion.

About the company

Tailscale builds a zero-config mesh VPN on WireGuard so teams can securely connect devices, servers, and cloud resources without traditional VPN complexity.

What you'll do

• Establish the Vancouver sales hub and hire and onboard Commercial Expansion AEs
• Drive expansion revenue, maintain pipeline health, and deliver accurate forecasts
• Coach reps through customer conversations and complex deals
• Build and refine a repeatable expansion playbook using sales data and customer insights
• Partner with Customer Success, Marketing, Product, Sales Engineering, and Partnerships to grow adoption

What we're looking for

• At least one year of people management experience in B2B SaaS sales
• Experience coaching and developing quota-carrying sales professionals
• Strong understanding of prospecting, discovery, qualification, pipeline management, and closing
• Experience using data, structured coaching, and accountability to drive team performance
• Ability to thrive in a fast-paced sales environment and manage multiple priorities
• Excellent written and verbal communication with technical and nontechnical stakeholders
• Curious, proactive mindset and willingness to travel approximately once per quarter
• Able to work from the Vancouver office three days per week

Benefits

• Equity incentive plan and variable commission
• Health, vision, and dental coverage with no waiting period
• Employer retirement contributions matched up to 0.75% of eligible compensation
• Flexible paid time off
• Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents
• Annual professional development allowance of $1,500 USD
• $500 USD home-office setup allowance and monthly internet reimbursement