April 7, 2021 4:00 am Published by

Episode 102:

Jill Proud is a dynamic facilitator, an experienced entrepreneur and a coach to senior leaders across Canada. Her passion lies in helping people see a bigger future for themselves, and her expertise lies in giving them the skills and motivation to make it a reality.

Jill built The Proud Group on a philosophy of only working where she can make a difference. Her powerful one-on-one coaching sessions with senior leaders and their teams is underpinned by her ability to connect in a real and deep way that allows clients to achieve their goals more quickly and easily.

As the Vice President of Sales for an international training firm, Jill drove expansion into the financial services industry while managing relationships with several large banking clients. As the Director of Sales and Marketing for another training firm, she expanded a licensee network of associates by 100%, including leading a cross-border expansion into the U.S. market. Jill’s diverse background also includes a project with the Canadian International Development Agency in the Chilean city of Santiago and consulting work throughout North America. Jill launched her career working as a facilitator and leader in the not-for-profit sector building local, national and international partnerships between municipalities,
businesses and not-for-profit organizations to establish inter-sectoral collaboration.

Through all of her roles, Jill witnessed first-hand the power of coaching, and the discipline necessary to coach effectively while under pressure. Jill has successfully brought this experience to bear in workshops for thousands of managers across the world. Whether she is teaching financial services executives in Toronto, working with leaders at Queen’s Smith School of Business or coaching CEOs in the complex healthcare environment, Jill marries energy and enthusiasm with the practicality that comes from real, lived experience.

In January 2019, Jill launched the Women Presidents’ Organization South Georgian Bay Chapter. WPO is the premier peer advisory organization connecting women who own multi-million dollar companies. This peer group approach fosters members to accelerate business growth and acts as a vital support network.

Outside of the business world, Jill has supported the work of Performance Coaching Inc. in their work with Hockey Canada. For two Olympic Games, she has brought her experience as a certified TAIS coach to bear in 1-to-1 coaching sessions with members of the Women’s National Team. She is also a passionate rower, and works locally to support learn to row programs. Jill lives in Collingwood, Ontario between the shores of Georgian Bay where she rows in the summer and the Niagara Escarpment where she cross-country skis in the winter. She has held a number of Board positions including as a Director on the Collingwood General and Marine Hospital Board. Jill is a founding member and current past Chair of Women in Philanthropy for Providence that has raised more than 900K in the funding to support special projects at Providence Healthcare in Toronto.

What you’ll learn about in this episode:

  • What holding space means in the coaching community
  • The top 3 challenges that women face with mindset
  • How September 11th impacted Jill’s decision to leave her corporate job
  • How the current state of the world is impacting the landscape of the work environment
  • How will we emerge from the pandemic


Digging Deep

Jill Proud is an entrepreneur and coach to senior leaders throughout Canada. In 2019, she founded the Women Presidents’ Organization South Georgian Bay Chapter. Jill has dedicated herself to making an impact in women’s lives, helping them to get vulnerable and find their power. In this episode of the Intentional Greatness® podcast, Jill joins us to share her inspiring story, and how she guides women in answering the pivotal question “Why am I here?”

Pivotal Moments

After an impressive corporate career in sales and marketing, Jill’s climb on the corporate ladder came to a screeching halt. The September 11th tragedy caused her to ask herself tough questions. This pivotal moment led her to make the decision to quit her job and pursue a career in coaching. It’s important to do work that feeds your soul and makes an impact. Jill shares how the current pandemic has affected women in a similar way as her 9/11 moment.

Redefining The What-If’s

Jill explains how the current state of the world is impacting the way that people work, particularly the way that women work moving forward. The pandemic has opened up the possibility of what our work lives could look like. She shares how we now have the opportunity to redefine the what-if’s to create a new version of our lives. It all begins with the questions: “why am I here?” and “what do I truly want?” Her incredible story of reflection and self-awareness shows that we are only as deep as our impact.

Download Your FREE Chapter of Chasing perfection

Get the first chapter of Sue’s book, Chasing Perfection: Shatter The Illusion along with the companion toolkit, the Maximizing Success Journal!