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 goalsDesign Claude-powered onboarding, coaching, call review, and deal preparationUse Gong and Salesforce data to identify coaching signalsGovern AI prompts, agents, workflows, quality,



and brand controlReport enablement performance and investment priorities to executivesRequirements:

Five-plus years in high-performance B2B technology sales organizationsThree-plus years as a direct-to-market quota-carrying individual contributorHands-on experience building AI and LLM business workflowsProven sales enablement programs with measurable resultsToronto-based or willing to relocate;

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

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