About Tailscale Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that is easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.
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 ( You will be the first sales leader to build out our new 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 advantages. 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.
For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.
CAN Pay Range (OTE) $268,000-$335,000 CAD
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📌 Manager, Commercial Expansion (Ontario)
🏢 Tailscale
📍 Ontario