Virtual Leadership Peer Group Facilitator - newmarket

Company Description

The Sterling Executive Group Inc. facilitates private executive leadership groups comprised of 10-12 C-level executives from non-competing industries. These groups meet regularly to enhance each member's leadership skills, advance organizational leadership maturity, improve work-life balance, achieve better business outcomes, and build strong personal and professional networks. Drawing on the principle that the wisest leaders learn from others' successes and failures, the organization fosters a collaborative, growth-oriented environment for its members.

Role Description

This is a remote, contract role for a Virtual Leadership Peer Group Chair. The Chair will guide group discussions, foster a collaborative environment, and help executives identify and overcome business challenges. Additional responsibilities include planning sessions, managing group dynamics, providing leadership insights, and ensuring a structured and productive meeting flow.

Sterling Program Architecture (Leadership Maturity System)

• Cross-regional C-Level peer groups (virtual by design) to maximize perspective diversity and reduce geographic constraint
• 12–15 half-day facilitated sessions per year focused on experiential peer learning through real leadership decisions and challenges
• Portfolio access to ~12 expert-led half-day workshops on relevant leadership and executive governance topics
• Paid, professional Sterling Chair facilitation to enforce rigour, constructive challenge, and disciplined peer dialogue
• Monthly private 1:1 leadership coaching to translate peer insight into sustained CEO behaviour change and leadership team maturity

Member Impact: improved decision quality, more substantial alignment, earlier risk detection, higher accountability, reduced CEO bottlenecks, improved team leadership maturity, and increased institutional resilience, all enabling sustainable growth.

Qualifications

• Strong facilitation, communication, and interpersonal skills
• Proven ability to guide and manage group discussions constructively
• Experience in executive leadership, coaching, or business management
• Solid understanding of business strategies, leadership principles, and organizational dynamics
• Comfortable with remote work platforms and virtual collaboration tools
• Ability to handle confidential information with discretion and professionalism
• Experience in business development and value proposition presentations
• Previous experience in executive peer group facilitation or similar roles is a plus
• Business-grade bilingual skills (French/English) are a plus