Who are you?
You are a passionate coach and builder—someone who gets fired up about helping others reach their full potential. You’re energized by the idea of leveling up a sales team through targeted onboarding, skill-building, and continuous improvement. You understand that great enablement is about more than training—it’s about building confidence, consistency, and excellence across the entire sales process.
You thrive in collaborative, high-growth environments where you can have a tangible impact. You’re equal parts strategist and executor, turning moving parts into streamlined structures. You strive to make the sales team better, faster, and more effective every day to ensure individual and team revenue targets are met. With your natural communication skills and your deep understanding of the sales cycle, you create programs and playbooks that are insightful and practical, and drive results.
You’re curious, proactive, and never satisfied with “good enough.” You seek feedback, analyze performance, and iterate quickly to keep content relevant and outcomes measurable. Above all, you care about people—and you believe that when sales teams feel prepared and supported, they perform at their best.
Sound like your kind of challenge? Keep reading.
What you’ll do…
- Build and continuously improve a structured, high-impact onboarding experience for new sales hires that reduces ramp time and boosts early success
- Own and evolve the Xello sales playbook, ensuring clear, up-to-date guidance on messaging, processes, buyer personas, objection handling, and other key areas of knowledge
- Deliver engaging skill-building sessions across key stages of the sales cycle, including discovery, demos, storytelling, negotiation, and closing
- Coach and upskill sales reps on delivering high-impact product demonstrations that resonate with different buyer personas
- Create engaging, bite-sized learning resources, certifications, and workshops to reinforce key concepts and best practices
- Collaborate with sales leaders to identify performance gaps and proactively implement targeted enablement strategies to address them
- Gather feedback from the sales team to continuously improve enablement materials, and stay responsive to their evolving needs
- Partner with marketing and product teams to support new feature rollouts and clarify messaging and competitive positioning so reps understand it, adopt it, and apply it in real-world conversations
- Track and report on enablement effectiveness using metrics like ramp time, content usage, win rates, quota attainment, and sales performance improvements
- Champion a culture of trust, learning, excellence, and continuous improvement across the sales team
What we’re looking for…
- 5+ years experience in sales enablement, sales training, sales coaching, or revenue enablement in a B2B SaaS environment
- Strong understanding of the B2B sales cycle, from prospecting and discovery through to demo, objection handling, and closing
- Proven track record of building and delivering onboarding and upskilling programs that drive measurable outcomes
- Experience developing and maintaining sales playbooks, talk tracks, demo scripts, and training content
- Confident facilitator and coach with excellent communication and presentation skills
- Strong project management skills and a bias for action—ability to juggle multiple priorities with focus and precision
- Empathetic and approachable nature, with the ability to build trust quickly with reps at all levels
Nice to have...
- Familiarity with tools like Salesforce, Chorus/Gong, Highspot, and other similar enablement platforms
- Experience working in or with K–12 education or EdTech sales teams
The compensation for this role offers an OTE ranging from $95,000 CAD to $115,000 CAD including base salary and incentive. The final offer will be determined based on the candidate's experience and expertise, as assessed during the interview process.
