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.