About the Role

We are looking for a gritty, thoughtful, and curious Sales Manager to lead an Expansion (existing customers) sales team focused on the Commercial segment (<750 employees). The Commercial team balances both a high velocity sales motion (7 to 13 opportunities per month) and occasional large opportunities ($50,000-$100,000 ACV contracts).

You will be the first sales leader to build out our recent Toronto sales hub. If you are looking for an opportunity to lead from the front and to build a repeatable sales machine from the ground up, this is it.

Key Responsibilities

- Become an expert in how Tailscale helps our customers
- Lead a team of account executives from the front - prospecting with the team, leading role plays, unblocking critical opportunities, and traveling to customers to build relationships
- Establish and refine best practices for pipeline generation, opportunity management, and customer relationship building
- Develop and coach the team using sales data, performance metrics, and sales enablement
- Work closely with marketing, product, sales engineering,



and partnership teams to create pipeline and accelerate opportunities

What We Are Looking For

- 1 years of sales management experience in a B2B SaaS/Software company
- Aptitude for delivering world-class customer experiences: operate with a sense of urgency, exercise curiosity about customers, and strive to add value in your interactions
- Excellent written and verbal communication skills
- Ability to manage many activities and tasks simultaneously
- Ability to travel to industry events once a quarter
- This role is based in Toronto and is hybrid required (3 days/week in-office).

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

📌 Manager, Commercial Expansion (Canada)
🏢 Tailscale
📍 Canada