Own and support the sales planning and performance lifecycle, including target setting support, achievement‑to‑plan management, and inputs into forecasting and capacity planning
Evaluate and manage pipeline health, velocity, and quality, including coverage ratios, stage progression, conversion rates, deal hygiene, and risk identification
Translate sales strategy into clear activity and execution models that align day‑to‑day sales activity with pipeline generation, deal progression, and revenue outcomes
Design, maintain, and continuously improve sales performance and pipeline dashboards/heat maps, delivering actionable insights on progress, gaps, risks, and opportunities
Partner with sales leaders to identify coaching and performance improvement opportunities based on pipeline behavior, deal execution, and performance trends
Lead sales onboarding, training, and ongoing capability development, including playbooks, frameworks, and best practices focused on execution excellence and pipeline discipline
Own the sales technology roadmap, acting as the business owner for CRM, sales enablement tools, pipeline management, reporting platforms, and workflow optimization
Serve as the central representative and voice of Sales for innovation initiatives, workshops, pilots, and cross‑functional programs, consolidating feedback and ensuring sales priorities are clearly represented
Requirements Post‑secondary degree/diploma in Business, Commerce, Finance, or a related field (required)
5-7 years of experience in sales enablement, sales operations, revenue operations, or sales performance roles (required)
Proven experience supporting sales planning, target setting, achievement‑to‑plan analysis, and performance management (required)
Strong experience evaluating pipeline health, velocity, and quality, including conversion rates,



deal progression, and forecast confidence (required)
Hands‑on experience designing and delivering sales onboarding, training programs, and coaching frameworks (required)
Experience acting as a business owner for CRM and sales technology platforms (e.g., Salesforce), including roadmap ownership and adoption (required)
Strong analytical skills with the ability to translate data into transparent insights and actions (required)
Excellent written and verbal communication skills, including executive‑level storytelling (required)
Fluent communication skills in English are required and bilingual skills in French are an asset
Highly organized, proactive, and comfortable operating in ambiguity (required)
Experience in wealth management, online brokerage, or financial services (preferred)
Core Competencies Demonstrates expertise in sales planning, performance management, and pipeline evaluation, with a strong focus on data analysis and actionable insights. Proficient in designing training programs and managing CRM technologies to enhance sales effectiveness and operational efficiency.
Highest-signal resume keywords Sales Planning
Pipeline Management
CRM Ownership
Data Analysis
Sales Training
ATS Optimization Keywords Hard Skills Sales Enablement
Performance Management
Target Setting
Pipeline Health Evaluation
Deal Progression Analysis
Forecast Confidence
Sales Onboarding
Coaching Frameworks
Analytical Skills
Sales Strategy Execution
Soft Skills Excellent Communication
Organizational Skills
Proactive Approach
Comfortable in Ambiguity
Executive-Level Storytelling
Industry Keywords Wealth Management
Online Brokerage
Financial Services
Tools & Technologies CRM Platforms
Salesforce
Sales Enablement Tools
Reporting Platforms
Pipeline Management Tools

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📌 Sales Enablement Lead (Ontario)
🏢 Jobtailor
📍 Ontario