Sales Enablement Lead

Jobtailor; Toronto; On-site; CAD 85,000 - 120,000; Full time

Job summary

Jobtailor in Toronto is seeking a Sales Enablement and Operations leader to own planning, forecasting, and pipeline discipline, aligning activities with revenue outcomes.

You will design dashboards, coach teams, manage CRM roadmap (Salesforce), and partner with sales leaders on onboarding and performance. English fluency required, French a plus.

Qualifications

• Post-secondary degree in Business/Finance required.
• 5–7 years in sales enablement/operations roles.
• Experience supporting planning, target setting, and performance management.
• Experience evaluating pipeline health, velocity, and conversion rates.
• Experience designing onboarding and coaching frameworks.
• CRM ownership including roadmap (e.g., Salesforce).
• Strong analytical skills and executive storytelling ability.
• English fluency; French a plus.

Responsibilities

• Own and support the sales planning and performance lifecycle, including target setting, achievement-to-plan analysis, and forecasting inputs.
• Evaluate and manage pipeline health, velocity, quality, coverage ratios, stage progression, and risk identification.
• Translate sales strategy into clear activity and execution models aligning daily work with pipeline and revenue outcomes.
• Design, maintain, and improve sales dashboards/heat maps, delivering actionable insights on progress, gaps, risks, and opportunities.
• Partner with sales leaders to identify coaching and performance improvement opportunities from pipeline behavior and trends.

Skills

Sales Enablement

Sales Operations

Revenue Operations

Pipeline Management

CRM Ownership

Data Analysis

Executive-Level Communication

Target Setting

Forecasting

Coaching Frameworks

Education

Post-secondary degree/diploma in Business, Commerce, Finance, or related field

Tools

CRM Platforms

Salesforce

Sales Enablement Tools

Reporting Platforms

Pipeline Management Tools

Job description

• 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 clear 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