Drive sales readiness and improve sales outcomes by shortening sales cycles and increasing wins

Build onboarding, certification, and content programs for sales, customer success, and sales development representatives

Design and deliver structured 30-60-90 day onboarding programs

Build role-based certification paths tied to product knowledge, MEDDPICC, and objection handling

Maintain onboarding scorecards and optimize programs using ramp-performance data

Operationalize sales plays for recent logo acquisition, expansion, and competitive displacement

Create talk tracks, discovery frameworks, demo flows, and repeatable selling frameworks

Partner with Product Marketing to translate positioning into field-ready enablement assets

Train teams on MEDDPICC and other qualification frameworks

Build deal-review templates and QBR-readiness checklists

Enable managers to improve pipeline reviews and forecast calls

Build and own Texada’s sales enablement knowledge base

Stand up and tune an AI assistant for mid-deal seller questions

Govern, refresh, and retire content as the product evolves

Measure knowledge-base and AI-assistant adoption, answer quality, and failure points

Track and report onboarding, certification, pipeline-quality, and conversion metrics

Iterate programs using win/loss analysis, deal-inspection findings, and frontline feedback

Requirements

4–6 years in sales enablement, sales operations, customer success, or quota-carrying sales at a B2B SaaS company

Account Executive or Sales Development experience is a strong plus





Hands-on experience using a sales methodology such as MEDDPICC or Challenger

Experience with onboarding or certification programs that reps actually use

Experience translating product marketing positioning into sales assets and messaging

Hands-on experience structuring content for AI retrieval

Experience building or tuning an AI assistant or knowledge tool in a GTM setting

Practical prompt design experience

Candidates must be authorized to work in Canada without restriction or sponsorship

Core Competencies Demonstrates expertise in sales enablement and operations, with a strong focus on developing onboarding and certification programs that enhance sales performance. Proficient in utilizing sales methodologies like MEDDPICC and building AI-driven tools to support sales teams.

Highest-signal resume keywords

Sales Enablement

Onboarding Program Development

MEDDPICC Methodology

AI Assistant Development

B2B SaaS Experience

ATS Optimization Keywords Hard Skills

Sales Methodology

Onboarding Programs

Certification Programs

Content Structuring

Prompt Design

Sales Metrics Tracking

Deal-Review Templates

QBR-Readiness Checklists

Sales Play Operationalization

Win/Loss Analysis

Soft Skills

Training

Collaboration

Communication

Feedback Iteration

Performance Optimization

Industry Keywords

B2B SaaS

Sales Operations

Customer Success

Quota-Carrying Sales

Product Marketing

Tools & Technologies

AI Assistant

Knowledge Base

Sales Enablement Tools

Sales Metrics Dashboards

Content Management Systems

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📌 Sales Enablement Specialist (Winnipeg)
🏢 Jobtailor
📍 Winnipeg