268K–335K CAD / year
Manager, Commercial Expansion
SalesHybrid — Toronto, Canada
Published on 2026-11-06
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About this role
Lead and grow a team of Commercial Account Executives focused on expanding existing customer relationships. As Tailscale’s first sales leader in Toronto, establish the local sales hub, hire and coach the team, 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 Toronto sales hub and hire and onboard Commercial Expansion Account Executives
- Drive expansion revenue, maintain pipeline health, and deliver accurate forecasts
- Join reps in prospecting and customer conversations to support expansion and complex deals
- Coach reps through call reviews, role plays, and deal strategy sessions
- Build and refine an 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 1 year of people management experience in B2B SaaS sales
- Track record coaching, developing, and motivating quota-carrying sales professionals
- Strong grasp of prospecting, discovery, qualification, pipeline management, and closing
- Experience improving team performance through data-driven decisions, structured coaching, and accountability
- Able to thrive in a fast-paced, high-velocity sales environment
- Excellent written and verbal communication with technical and nontechnical stakeholders
- Curious, proactive, and committed to continuous improvement
- Willing to travel approximately once per quarter
Benefits
- Equity incentive plan and variable commission for quota-based roles
- Health, vision, and dental coverage with no waiting period
- Employer retirement contributions matched dollar-for-dollar 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 funding of $1,500 USD
- Company laptop, monthly home internet reimbursement, and $500 USD for home-office setup
- Annual company retreat and team off-sites