Ai-First Sales Enablement Manager

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.

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