Job Specifications
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
Reports to: Sales Enablement Manager
About Us:
At WellnessLiving, we empower thousands of health and wellness business owners to turn their entrepreneurial dreams into reality. Our mission-critical software fuels their vision, supporting millions of clients around the world in their wellness journeys. With a deep commitment to putting our customers first, we foster a culture that values high performance, adaptability, and accountability. If you are a skilled professional who thrives in a fast-paced, customer-focused environment and are passionate about making a meaningful impact on the health and wellness industry, we would love to connect with you.
At WellnessLiving, our team is driven by four core values that shape everything we do. If you share these values and meet the qualifications outlined for this role, we encourage you to apply - we’d love to learn more about you!
Customer First – We approach every challenge with a customer-focused lens, driven by an obsession with our customers’ happiness and success.
Excellence – We approach every task, whether big or small, with a steadfast commitment to exceptional execution and the pursuit of greatness.
Accountability – We take full ownership of our decisions, actions, and outcomes – both successes and failures.
Adaptability – We recognize that sustained success demands that we be malleable and purposefully evolve, acknowledging that the world is dynamic and constantly changing.
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 Gong 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 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., predictiv
About the Company
Our powerful business management software is trusted by thousands of spas, salons, fitness and yoga studios across North America. Our cloud based software features real-time appointment and class scheduling, point of sale, email and SMS marketing, customer review management, rewards program and a client mobile app experience that is second to none. Our mission is to provide the wellness industry with the most comprehensive tool set available to better manage their existing clients while helping them grow their business.
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