CareerPlan

Head of Sales

TorontoFull-timeCA$145k–CA$190k2026-10-27 → 2026-11-10
On-site

Core

Lead the sales organization for an AI agent platform serving mid-market and enterprise B2B clients, carrying your own book of business while hiring and coaching Account Executives.

Role type

Head of Sales (Player-Coach)

Builds

Sales team, playbooks, and processes for an AI agent platform

Domain

B2B SaaS / AI

Required skills

B2B SaaS sales leadership, closing mid-market and enterprise deals, hiring and coaching sales teams, building sales playbooks, forecasting and pricing strategy

Preferred skills

Experience selling to support, CX, IT, or digital leaders

Technologies

AI agents, Chatbase platform

Responsibilities

Close your own mid-market and enterprise deals, hire and lead the Account Executive team, set standards for discovery and forecasting, provide feedback to product on customer needs

Seniority

Senior, hands-on IC with leadership responsibilities