Remote Sales Enablement Specialist

Title: Sales Enablement Specialist
Salary: Based on Experience + 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 Specialist, 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., 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. At WellnessLiving, we are proud to embrace and celebrate differences. Employment at WellnessLiving is based purely on a candidate’s qualifications and experiences as they directly relate to professional competencies. WellnessLiving does not discriminate against any employee or potential employee because of race, creed, color, religion, gender, sexual orientation, gender identity/expression, national origin, disability, age, genetic information, veteran status, marital status, family or parental status, or any other status protected by the laws and regulations in the locations where we operate. Furthermore, we will not tolerate bias or discrimination of any kind from our employees or customers. At WellnessLiving, we bring everyone together to create something incredible! We are a unique and diverse blend of leaders and action-takers, and that mindset encompasses our passion and commitment to our product and our employees.

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.