Jennifer Wilson
Founder and Lead Coach @ Oak Bay Coaching and Consulting
About
Are you a leader, part of a family business, or an organization seeking executive coaching to enhance team dynamics, resilience, and performance? I specialize in helping leaders and teams unlock their potential, turning challenges into growth opportunities. As a Leadership Coach, Writer, and Facilitator, I combine my expertise in leadership development, team building, and personal growth with a compassionate approach. My work is grounded in the belief that everyone has unique strengths waiting to be harnessed, and with the right guidance, we can achieve extraordinary results. My coaching is particularly focused on empowering new leaders, supporting family businesses, and guiding organizations through transformational change. I currently serve as the Chair of the Board for The Canada Homestay Network, a not-for-profit organization that manages homestay programs for over 35 school boards and 60 independent schools, language schools, colleges, and universities across Canada. My journey with the organization began in 2005 when I joined the family business, which was founded by my mother, Robin, in 1995. In 2010, I proudly stepped into the role of CEO, where I led the organization for 12 years, overseeing client satisfaction, business development, risk management, and quality assurance. Under my leadership, CHN flourished. Today, I continue to contribute as an expert in the field, regularly speaking at industry conferences on homestay standards and best practices. In addition to my coaching practice, I’m passionate about writing and sharing actionable insights. I publish the JRW Newsletter monthly, focusing on the art and intricacies of hosting successful homestays. Whether you’re looking to refine your leadership style, enhance your writing skills, or create meaningful homestay experiences, my newsletter offers practical advice with a warm, approachable tone. My professional journey has been diverse, from leading a national organization to practicing as a Registered Midwife. These roles have deepened my expertise in leadership, risk management, and wellness, particularly in high-stress environments. I’m also a certified Kolbe consultant and have specialized training in Crisis Intervention and Compassion Fatigue, which informs my approach to building resilience and well-being. Let’s connect! If you’re interested in executive coaching, leadership development, team dynamics, writing, or the homestay industry, I’d love to hear from you. And don’t forget to check out my newsletter for monthly insights on homestays, leadership, and more.
Canada
Victoria
Higher Education
Board Leadership, Compassion Fatigue, Human Resources (HR), Strategic Human Resources Leadership, Standard Operating Procedure (SOP), Payroll Management, Technical Support, Information Technology, Web Development, IT Infrastructure Management, Budgeting, Policy Development, organizational coaching, Public Speaking, Strategic Planning, Coaching, Team Building, Leadership, Change Management, Leadership Development
Experience

Chief Executive Officer
o Responsible for developing strategic plans, overseeing financial affairs, setting budgets, providing long-range forecasting, and directing community operations across Canada; o Responsible for management of 125 employees; o Delivered over 30 workshops and lectures to educators, agents, and homestay providers at international education conferences and trade fairs since 2010 o Designed and developed a professional development program and delivered bi-weekly training webinars; o Created and maintained operational policies, procedures, training manuals and orientations; o Involved in development of Family Business Council and new governance structures for the business; successfully developed and implemented succession plan in 2022.

Chief Technology Officer
o Managed corporate technical resources to expand reliability and available features; o Responsible for new associate installation of and training on CHN systems including corporate database, email, VoIP phone and instant messaging; o Provided ongoing technical support to all employees; o Managed and maintained website and client portals.

Senior Human Resources Manager
o Developed recruitment, screening, hiring, promotion and termination policies; o Created standardized job descriptions, related pay scales and a payroll system; o Created and managed standardized annual performance review process; o Researched, implemented and managed extended health benefits plan; o Designed and maintained client documents, including guides, evaluations and agreements.

Board of Directors
Family Business Association Vancouver Island
Victoria BC

Registered Midwife
Winnipeg Regional Health Authority, Salt Spring Midwives, Cook Street Community Midwives, etc.
Victoria, British Columbia, Canada
Practiced in two provinces and trained in the US and Belize, with experience in shared care and solo practices, in both urban and rural settings. Responsible for clinical and administrative aspects of practice. • President, Midwives Association of Manitoba (2001-2002) • Member, College of Midwives of Manitoba Standards Committee (2000-2002) • Student Representative, Midwives Association of BC Board of Directors (1997-99)
Jennifer Wilson's Contact Information
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