CareerPlan

Sales Manager, Mid-Market

CA - ON - Toronto - RemoteFull-timeCA$172k–CA$257k2026-10-23 → 2026-11-10

Core

Lead a team of Senior Account Executives on a fully outbound sales team to drive growth for Square's mid-market sellers through strategic pipeline development and talent coaching.

Role type

Senior Sales Manager (Outbound Team Lead)

Builds

High-performance sales organization and predictable revenue outcomes for mid-market sellers

Domain

Fintech / Payments / SMB Commerce

Required skills

Outbound sales strategy, team leadership, pipeline management, forecasting, data-driven coaching, hiring, cross-functional partnership

Preferred skills

Experience leading high-performing teams in fast-paced environments, ability to balance short-term execution with long-term organizational health

Technologies

CRM, Sales Intelligence Tools, BI Platforms

Responsibilities

Hire and develop Senior Account Executives, coach reps on pipeline health and forecasting, establish operating rhythms for revenue predictability, partner with leadership and product to improve the customer journey

Seniority

Senior, hands-on IC with team leadership