Remote Sales Enablement Trainer; Richmond

Job Overview

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

At Wellness Living, 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.

Our team is driven by four core values that shape everything we do:

• 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.

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.

• 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.
• 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.
• 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.
• 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.
• 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.

• 3+ years of experience in sales enablement, sales training, or a frontline SaaS sales role (BDR/AE) in a high‑velocity setting.
• 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…