Remote Sales Enablement Specialist; Paradise

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

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.

We are 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 commit to exceptional execution and the pursuit of greatness in every task.
• Accountability – We take full ownership of our decisions, actions, and outcomes.
• Adaptability – We recognize that sustained success requires purposeful evolution in a dynamic world.

As a Sales Enablement Specialist, you’ll design and deliver impactful training and coaching programs that elevate our high‑velocity sales team. You’ll partner with new hires and experienced sales professionals to motivate, educate, and inspire through structured classroom sessions or informal mentorship. Your work will champion the needs of the sales team, streamline workflows, and drive strategic enablement initiatives to 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 (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 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 (SPIN, Challenger, BANT); certification is 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 to optimize sales strategies and conversion outcomes.

• Work with a passionate, energetic,…