Manager, Commercial Expansion
Tailscale — Hybrid (Toronto, Ontario)
Posted 2026-08-11
About Tailscale Tailscale is making safe connection effortless 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's 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 (<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 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