Contractor Leadership Coach and Facilitator

Job summary

Deliver individual coaching focused on career transitions and leadership development for mid-senior level professionals. Facilitate interactive, inclusive workshops for corporate teams across Canada using modern adult learning principles.

Job details

Leadership & Transition Coach & Facilitator (Private Sector / Mid-Senior Level) Coaching & Facilitation — National / Remote (Bilingualism an Asset) Locations: Edmonton, Calgary, Halifax, Saskatoon, Regina, The Maritimes The Partnership: Impact Through Coaching & Facilitation Work fundamentally shapes the quality of our collective lives. As a growing leadership professional, you are likely looking for a partnership where your talent meets a real mission—a place where you can expand your practice, collaborate with incredible teams, and make a tangible difference in people's daily work lives. At CareerJoy, we provide a platform for dynamic coaches and facilitators to engage with managers, mid-level leaders, and professionals across Canada. We believe that when you support an individual through a critical career pivot or help a team build authentic leadership presence, you elevate the entire organization. This is a space for those who thrive on practical wisdom, human connection, and modern adult learning. Our Impact: We are an award-winning boutique HR services firm partnering with over 2,300+ of Canada's leading companies—including World Vision, Shopify, Toyota Manufacturing, and The United Way. Our work is defined by being Human, Modern, Canadian, and Results-Driven. The Role: Leadership & Transition Partner Unlocking Potential, Leadership Presence & Modern Adult Learning We are seeking an energetic, tech-savvy Leadership & Transition Coach & Facilitator who geeks out on modern adult learning, interactive workshops, and human-centred career development. In this role, you aren't just delivering content—you are creating transformational experiences. You will work directly with emerging managers, mid-level leaders, and cross-functional teams in the corporate and private sectors nationwide. Whether guiding someone through a career transition, helping a new manager establish their leadership presence, or facilitating an inclusive, high-energy workshop, your goal is simple: make work better. What You’ll Do Leadership & Career Transition Coaching Transition & Outplacement Support: Deliver engaging individual coaching focused on career pivots, transitions, and onboarding. Guide professionals through career shifts and outplacement with empathy, practical strategies, and constructive accountability. Leadership Coaching: Deliver 1:1 coaching across key leadership capabilities, including building leadership presence, strategic communication, emotional intelligence, managing team dynamics, handling difficult conversations, and navigating career transitions. Fit: Conduct warm, structured initial "meet and greet" sessions to build trust, uncover goals, and map out clear, actionable coaching journeys. Interactive Workshop & Group Facilitation Dynamic Facilitation: Lead highly engaging, inclusive, and practical workshops for corporate teams across Canada (both virtually on MS Teams/Zoom and occasionally on-site). Adult Learning Enthusiast: Bring dynamic adult learning principles to life—fostering open discussion, psychological safety, and real-world skill application. Delivery Collaboration: Partner closely with our People and Culture Team to ensure seamless workshop setup, tech integration, and post-session follow-through. Position Requirements The "Must Haves": Professional Background: 3–5+ years of experience in mid-to-senior management, L&D, talent development, or professional coaching/consulting within the private sector. Transition & Leadership Expertise: A proven passion and knack for helping people navigate career transitions and build authentic leadership presence. Facilitation Mastery: Demonstrated experience delivering interactive, inclusive, and engaging group workshops or team training sessions. Tech-Savvy & Adaptable: Comfortable and confident fluency with modern virtual tools (MS Teams, Zoom, digital whiteboards, CRM/M365 environments). Coaching Credentials or Experience: ICF Accreditation (ACC/PCC), active candidacy toward ICF certification, OR equivalent formal leadership/coaching experience. Key Assets (Nice to Haves): Bilingualism: Professional proficiency in both French and English (a strong asset for national corporate engagements). Assessment Tools: Certification or debriefing experience in tools such as EQi2.0, DiSC/Insights, or 360 feedback surveys. L&D Frameworks: Familiarity with modern learning models (e.g., 70/20/10) and interactive design. How We Work: The 4Cs of CareerJoy Commitment: We lead ourselves first, then others; we seek feedback and embrace progress over perfection. Character: We bring an energetic, resilient, and human presence to everything we do—doing what’s right over what’s easy. Competency: We blend strategic insight with intuitive coaching, listening deeply and leveraging tech to constantly improve. Culture: We thrive in a culture of mutual respect, humour, and trust—showing up with compassion, agility, and heart. Next Steps to Explore This Fit Along with your resume, please send us a quick 2-minute video sharing: What excites you most about supporting people through leadership transitions? How you keep participants engaged and included when facilitating modern virtual workshops.

What you’ll do

Deliver individual coaching focused on career transitions and leadership development for mid-senior level professionals. Facilitate interactive, inclusive workshops for corporate teams across Canada using modern adult learning principles.

Requirements

Requires 3-5+ years of experience in management, L&D, or professional coaching within the private sector. Proficiency in virtual collaboration tools and a strong background in leadership presence and facilitation are essential.

Listed skills

• Zoom · Preferred
• Facilitation · Preferred
• CRM · Preferred

Other relevant skills

Identified from the job description. Confirm important requirements above.

• Leadership Coaching
• Facilitation
• Adult Learning
• Career Transition
• Outplacement Support
• Strategic Communication
• Emotional Intelligence
• Team Dynamics
• Workshop Design
• Virtual Facilitation
• MS Teams
• Zoom
• CRM
• M365
• Talent Development
• 360-Degree Feedback
• Interactive Design
• Empathy
• Microsoft 365
• Energetic
• Building Trust
• Accountability
• Follow Through
• Zoom (Video Conferencing Tool)
• Resilience
• Bilingual (French/English)
• Compassion
• Microsoft Teams
• Adult Education
• Adult Learning Principles
• Customer Relationship Management
• Management
• Consulting
• DISC Assessments
• Leadership
• Psychology
• Video Hosting Services
• Operations
• Coaching
• Surveys
• Technical Acumen

Job areas

• Human Resources
• Management & Leadership
• Consulting
• Education
• Leadership Facilitator
• Career Counselor
• Personnel and Careers Professionals
• Educational, Guidance, and Career Counselors and Advisors

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