Manager, Commercial Expansion

The role

You will lead a team of Commercial Account Executives focused on growing existing customer relationships. You will coach reps, own team performance, and help establish a new sales hub in Vancouver.

What you will do

• Establish Tailscale's new sales hub and hire and onboard Commercial Expansion AEs
• Drive expansion revenue, maintain a healthy pipeline, and deliver accurate forecasts
• Prospect alongside reps and join customer conversations
• Navigate fast-moving expansions and larger, more complex deals
• Provide coaching through call reviews, role plays, and deal strategy sessions
• Build and refine a repeatable expansion playbook using sales data and customer insights
• Partner with Customer Success, Marketing, Product, Sales Engineering, and Partnerships

Required 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
• 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

Benefits

• Base salary, equity incentive plan and variable commission
• Comprehensive group benefits with no waiting period
• Employer-funded retirement contributions (up to 0.75% of eligible compensation)
• Annual company retreat and team off-sites
• Corporate co-working program
• $1500 USD annually for professional development
• Mentorship, coaching, and internal promotion opportunities
• Flexible, paid time off program
• Company-owned laptop (Mac or PC)
• Monthly home internet reimbursement
• $500 USD to customize workstation
• Paid parental leave program

Before you apply

• Hiring process uses AI-assisted tools to help screen and assess candidates

About the company

Tailscale delivers software that makes it easy to securely interconnect people and their devices. Founded in 2019, the company is fully distributed and backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.