Role Overview The Senior Revenue Enablement Specialist, Digital will play a key role in designing, delivering, and optimizing strategic enablement programs that empower go-to-market teams, strengthen sales execution, and drive measurable business results.

What You Will Do The ideal candidate will lead the design, implementation, and continuous improvement of MEDDPICC qualification frameworks, partner with sales leaders to strengthen deal qualification, and leverage CRM data to identify performance gaps and develop targeted coaching initiatives.

Why It Might Be a Fit The ideal candidate combines strategic thinking with hands-on execution, thrives in a dynamic global environment, and brings a passion for developing people, improving processes, and driving measurable outcomes.

Requirements

8+ years of experience in revenue enablement or sales enablement within B2B software or SaaS environments

Proven experience designing, implementing, and managing enablement programs across multiple regions, business units, or solution portfolios

Solid expertise in MEDDICC/MEDDPICC methodologies, including implementation, coaching, qualification standards, and deal inspection across Mid-Market and Enterprise sales environments

Demonstrated success developing sales onboarding, certification, coaching, and performance improvement programs

Experience measuring the effectiveness of enablement initiatives through commercial outcomes such as win rates, pipeline conversion, quota attainment, ramp time, or recurring revenue

Strong facilitation and presentation skills, with experience delivering engaging training to sales professionals, customer success teams, and leadership





Experience developing practical, self-service sales enablement resources that drive adoption and support independent learning

Strong analytical skills, with the ability to interpret CRM data, conversation intelligence, and learning platform analytics

Experience using generative AI tools to enhance content development and operational efficiency

Excellent stakeholder management, communication, and relationship-building skills

Ability to manage multiple projects simultaneously, navigate competing priorities, and deliver high-quality results in a fast-paced environment

Strong change management capabilities, including driving adoption and reinforcing new processes and learning initiatives

Excellent written and verbal communication skills in English

Experience collaborating with global teams across North American and European time zones

Benefits

Flexible Work

Endless Learning

Inclusive Community

Comprehensive Rewards

Caring for Wellbeing

Read by ReLoop.me A hands-on expert who designs and runs the MEDDPICC qualification approach and uses CRM data to target coaching across global sales teams.

Level (indicative):

Expert.

Title vs scope:

aligned.

Requirement inflation:

low.

Shape of the role:

strongly individual contributor; leans build / define.

Core capabilities:

MEDDPICC framework design and implementation, deal qualification and deal inspection and CRM and conversation intelligence data analysis.

Not for you if

you want to manage a team directly, or you need a clearly bounded scope.

Indicative, AI-generated read, no salary range. Full read and sourcing ReLoop.me

📌 Senior Revenue Enablement Specialist, Digital (Markham)
🏢 RevOps Careers
📍 Markham