Sales Enablement Trainer

Title: Sales Enablement Trainer  
Salary: $70,000 - $80,000 + Benefits + Vacation 
Location: Thornhill, Ontario
Hybrid (in-office 3 days per week)
Length: Full-time, Permanent 

About Us: 

At WellnessLiving, we empower health and wellness business owners to turn their passion into thriving businesses. Our mission-critical software supports thousands of entrepreneurs and millions of clients worldwide on their wellness journeys. We’re a customer-first company that values excellence, accountability, and adaptability, and we’re looking for people who thrive in a fast-paced environment and want to make a meaningful impact in the wellness industry. 

Our culture is guided by four core values that shape how we work and grow together: 

Customer First – We approach every challenge with a deep commitment to our customers’ success and happiness. 

Excellence – We hold ourselves to a high standard and strive for exceptional execution in everything we do. 

Accountability – We take ownership of our decisions, actions, and results. 

Adaptability – We embrace change, stay flexible, and continuously evolve in a dynamic world. 

If these values resonate with you and you meet the qualifications for this role, we’d love to hear from you! 

About You:

As a Sales Enablement Trainer, you’ll play a key role in designing and delivering impactful training and coaching programs that elevate the performance of our high-velocity sales team. You’ll partner with both new hires and experienced sales professionals to motivate, educate, and inspire, whether through structured classroom sessions or informal one-on-one mentorship. Your work will be instrumental in championing the needs of the sales team, streamlining workflows, and driving strategic enablement initiatives that fuel sales excellence and results.

Responsibilities:

Sales Coaching & Performance Support

• Lead structured 1:1 coaching sessions using CRM insights and call analytics.
• Review and score calls based on talk ratio, CTA usage, discovery quality, objection handling, and other key sales metrics.
• Document coaching outcomes and track rep progress over time.

Training Delivery & Content Development

• Design and deliver engaging training programs (both live and virtual) for sales reps at all experience levels.
• Build instructional materials such as talk tracks, role-play scenarios, call guides, case studies, videos, and job aids.
• Support onboarding by equipping new hires with the skills, tools, and knowledge to succeed from day one.

Enablement Culture & Peer Learning

• Foster a culture of collaboration through peer coaching, top-call reviews, and best-practice sharing.
• Partner with sales leaders to run recurring enablement sessions during team functions and meetings.

Program Evaluation & Continuous Improvement

• Assess program comprehension through quizzes, participation tracking, and follow-up coaching.
• Gather feedback through post-training surveys to improve relevance, delivery, and engagement.
• Regularly audit and update enablement content to reflect current priorities and best practices.

Enablement Operations & Cross-Functional Collaboration

• Coordinate the rollout of new sales training and coaching initiatives.
• Support performance evaluations to identify skill gaps and opportunities for growth.
• Collaborate with sales, product, and marketing teams on training for new offerings and methodologies.
• Stay current with industry trends and pursue ongoing professional development.

Skills & Qualifications:

• 3+ years of experience in sales enablement, sales training, or a frontline SaaS sales role (BDR/AE) in a high-velocity environment
• Bachelor's degree or equivalent practical experience
• Proven track record of leading live sales coaching, onboarding, call reviews, and training delivery
• Hands-on experience with Salesforce, Gong, and enablement platforms
• Familiarity with working alongside SDR/BDR teams in fast-paced sales orgs
• Strong understanding of sales methodologies (e.g., SPIN, Challenger, BANT), certification an asset
• Excellent written, verbal, and presentation skills—able to communicate complex ideas clearly and persuasively
• Skilled in facilitating adult learning and delivering engaging, high-impact instruction
• Adaptable, resourceful, and confident in navigating change and ambiguity
• Highly collaborative with a team-first mindset and strong performance standards
• Strong analytical skills and attention to detail, especially in structured documentation, performance metrics, and feedback processes
• Proficiency in Microsoft Office Suite
• Experience applying AI-driven insights (e.g., predictive analytics, automation) to optimize sales strategies and conversion outcomes

Why Work With Us?:

• Work with a passionate, dynamic, and fast-growing team dedicated to making a meaningful impact in the wellness industry.
• Competitive salary, vacation, and benefits package.
• Hybrid work environment with opportunities for career growth and development.
• Work in a culture that values creativity, collaboration, and continuous learning.

We appreciate you taking the time and look forward to reviewing your application! 

Please note that those who meet the qualifications for the position will be contacted directly. 

WellnessLiving is an equal opportunity employer. Employment decisions are based on qualifications, experience, and business needs. We prohibit discrimination and harassment of any kind and consider all qualified applicants without regard to race, color, religion, creed, gender, gender identity or expression, sexual orientation, national origin, disability, age, genetic information, veteran status, marital or family status, or any other status protected by applicable law. 

We utilize AI to generate summaries of interview notes as part of our candidate evaluation process. This helps ensure a fair and consistent review while maintaining a human-centered hiring approach.