Remote opportunity at
TailscaleManager, Commercial Expansion
Tailscale is seeking a Manager for Commercial Expansion to oversee a team of Commercial Account Executives focused on growing established customer relationships. Founded in 2019, the…
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About This Role
Tailscale is seeking a Manager for Commercial Expansion to oversee a team of Commercial Account Executives focused on growing established customer relationships. Founded in 2019, the organization builds secure networking and connection software designed for individuals and multinational corporations alike. In this position, you will act as the inaugural sales leader in Toronto, helping establish a new sales hub, mentoring team members, and building a repeatable expansion strategy. The role…
Job Description
Tailscale is seeking a Manager for Commercial Expansion to oversee a team of Commercial Account Executives focused on growing established customer relationships. Founded in 2019, the organization builds secure networking and connection software designed for individuals and multinational corporations alike. In this position, you will act as the inaugural sales leader in Toronto, helping establish a new sales hub, mentoring team members, and building a repeatable expansion strategy. The role requires working from the Toronto office three days per week and traveling approximately once per quarter.
This opportunity is suited for a professional who thrives in a fast-paced environment and possesses a background in B2B SaaS sales management. Responsibilities include driving revenue, maintaining pipeline health, delivering forecasts, and collaborating across departments such as Marketing, Product, and Customer Success. The total compensation package features a base salary ranging from CAD 268,000 to 335,000 per year, alongside equity and comprehensive group benefits with no waiting period.
Responsibilities
- Help establish the Toronto sales hub and hire Commercial Expansion Account Executives
- Drive expansion revenue, maintain a healthy pipeline, and deliver accurate forecasts
- Prospect alongside team members and participate in customer conversations to navigate key deals
- Conduct call reviews, role plays, and deal strategy sessions to provide practical coaching
- Build and refine a repeatable expansion playbook using sales data and customer insights
- Partner with Customer Success, Marketing, Product, Sales Engineering, and Partnerships to increase adoption
Requirements
- At least 1 year of people management experience in a B2B SaaS sales environment
- Demonstrated ability to coach, develop, and motivate quota-carrying sales professionals
- Solid understanding of the sales process including prospecting, discovery, qualification, pipeline management, and closing
- Ability to drive team performance through data-driven decisions and structured coaching
- Capacity to work from the Toronto office three days per week
- Willingness to travel approximately once per quarter
Core Skills
Benefits
- Base salary between CAD 268,000 and 335,000 per year
- Equity incentive plan and variable commission
- Comprehensive group benefits for health, vision, dental, and more with no waiting period
- Employer-matched retirement contributions up to 0.75 percent of eligible compensation
- Annual professional development budget of 1500 USD
- Flexible paid time off program
- Build-your-own home office setup including a company laptop, monthly internet reimbursement, and 500 USD for workstation customization
- Paid parental leave program offering 20 weeks for birthing parents and 16 weeks for non-birthing parents
- Opportunities to attend annual company retreats and team off-sites
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
What is the salary range for this role?
The target base salary for a new hire ranges from CAD 268,000 to 335,000 per year, with individual offers varying based on experience and skill set. The total compensation also includes equity and variable commission.
Where is this position located?
This role requires working from the company office in Toronto three days per week. Travel is also required approximately once per quarter.
What experience is required to apply?
Candidates must have a minimum of 1 year of people management experience within a B2B SaaS sales environment, along with a strong understanding of the full sales process and team performance management.
What benefits are provided?
Benefits include comprehensive health, dental, and vision coverage with no waiting period, dollar-for-dollar retirement matching up to 0.75 percent of eligible compensation, an annual professional development allowance, and paid parental leave.
Sample Interview Questions
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