Manager, Commercial Expansion

Tailscale

1d • CA$268,000 - CA$335,000 • Hybrid

About The Position

Tailscale is seeking a gritty, thoughtful, and curious Sales Manager to lead an Expansion sales team focused on the Commercial segment (<750 employees). This role involves managing a high-velocity sales motion with 7 to 13 opportunities per month, as well as occasional larger opportunities with contracts valued at $50,000-$100,000+. The successful candidate will be the first sales leader to build out Tailscale's new Toronto sales hub, with the opportunity to lead from the front and construct a repeatable sales machine from the ground up.

Requirements

• 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).

Responsibilities

• Become an expert in how Tailscale helps its customers.
• Lead a team of account executives from the front, including prospecting, 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.

Benefits

• Competitive total compensation package including base salary, equity incentive plan, and variable commission.
• Comprehensive group benefits with no waiting period for health, vision, and dental coverage for you and your family.
• Remote-first company with flexibility in how and when you work.
• Employer-funded retirement contributions with a dollar-for-dollar match up to 0.75% of eligible compensation.
• Opportunities to connect with colleagues through annual company retreats, team off-sites, and in-person collaboration.
• Support for personal and professional development with $1500 USD annually for professional development, mentorship, coaching, and internal promotion opportunities.
• Flexible, paid time off program for work-life integration.
• Home office setup including a company-owned laptop (Mac or PC), monthly home internet reimbursement, and $500 USD for workstation customization.
• Paid parental leave program (20 weeks for birthing parents, 16 weeks for non-birthing parents).

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed