Manager, Commercial Expansion - Tailscale

About Tailscale

Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices. From hobbyists to multinational corporations, teams of every size use Tailscale to protect their networks and share access to internal tools. Founded in 2019 and fully distributed, we are 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 sales team focused on the Commercial segment (<750 employees). You will be the first sales leader to build out our new Toronto sales hub, establishing a repeatable sales machine from the ground up.

Key Responsibilities

• Become an expert in how Tailscale helps our customers.
• Lead a team of account executives from the front: prospect with the team, lead role plays, unblock critical opportunities, and travel to customers.
• 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.
• Collaborate with marketing, product, sales engineering, and partnership teams to 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 with urgency and curiosity.
• Excellent written and verbal communication skills.
• Ability to manage multiple tasks simultaneously.
• Ability to travel to industry events once a quarter.
• Note: This role is based in Toronto and requires 3 days/week in-office.

What We Offer

• Competitive total compensation (base salary, equity, and variable commission).
• Comprehensive group benefits (health, vision, dental) with no waiting period.
• Employer-funded retirement contributions (up to 0.75% match).
• $1,500 USD annual professional development stipend.
• Flexible paid time off and parental leave top-ups.
• Home office setup: company laptop, monthly internet reimbursement, and $500 USD for workstation customization.
• Opportunities to connect with the team via company retreats and team off-sites.