# Manager, Commercial Expansion

**Company:** [Tailscale](https://hotfix.jobs/companies/tailscale)
**Location:** Toronto, Canada
**Role:** Account Management
**Salary:** CA$268k – CA$335k/yr
**Experience:** 5+ years
**Skills:** B2B SaaS, Sales Management, Pipeline Generation, Opportunity Management, Sales Enablement, Performance Metrics, Customer Relationship Management, Written Communication, Verbal Communication
**Posted:** 2026-08-12

> Leads a commercial expansion sales team focused on growing existing B2B SaaS customers, coaching account executives and building repeatable pipeline and opportunity-management practices. The role requires sales management experience, strong communication, customer focus, and hybrid work in Toronto.

## Job Description

## Responsibilities

- Become an expert in how Tailscale helps customers.
- Lead a team of account executives from the front through prospecting, role plays, opportunity support, and customer relationship building.
- 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 create pipeline and accelerate opportunities.
- Travel to industry events once a quarter.

## Requirements

- 1+ years of sales management experience in a B2B SaaS or software company.
- Aptitude for delivering excellent customer experiences, with urgency, curiosity, and a value-oriented approach.
- Excellent written and verbal communication skills.
- Ability to manage multiple activities and tasks simultaneously.
- Based in Toronto and able to work hybrid, three days per week in the office.

## Compensation and Benefits

- Target OTE compensation of **268000–335000 CAD**, inclusive of base salary and variable compensation tied to quarterly sales targets.
- Base salary, equity incentive plan, and variable commission for quota-based roles.
- Comprehensive group health, vision, and dental benefits.
- Employer-funded retirement contributions matching employee contributions up to a maximum annual employer contribution of 0.75% of eligible compensation.
- $1500 USD annually for professional development.
- Paid time off and paid parental leave.
- Company-owned laptop, monthly home internet reimbursement, and $500 USD for workstation customization.

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