Architect AI-first sales readiness at SysAid in Toronto, using Claude, MCP-connected systems, and data to scale global seller performance.

As Sales Enablement Manager, you will define how sales and customer success teams learn, prepare, and win. You will build enablement strategy, launch readiness, coaching systems, and AI-powered workflows. The role partners with Sales, Customer Success, Marketing, Product, and Revenue Operations to turn go-to-market strategy into seller behavior and measurable revenue outcomes.

Key Responsibilities

Own global enablement strategy and roadmap tied to revenue goals

Design Claude-powered onboarding, coaching, call review, and deal preparation

Use Gong and Salesforce data to identify coaching signals

Govern AI prompts, agents, workflows, quality,



and brand control

Report enablement performance and investment priorities to executives

Requirements

Five-plus years in high-performance B2B technology sales organizations

Three-plus years as a direct-to-market quota-carrying individual contributor

Hands-on experience building AI and LLM business workflows

Proven sales enablement programs with measurable results

Toronto-based or willing to relocate; four office days weekly

Shape SysAid’s AI-first enablement engine through Claude, sales analytics, coaching, and measurable global revenue impact.

📌 AI-First Sales Enablement Manager (Winnipeg)
🏢 SysAid
📍 Winnipeg