“If you always know where you are going, you’ll never know what you missed.”

— Kim Ross Jackson

Teaching, Coaching & Mentorship

As a Certified Skills & Strengths Discovery Coach (Cappfinity), I lead workshops and 1:1 coaching sessions that help students and professionals identify their realized and unrealized strengths and learned skills. That work is grounded in my M.S. in Organizational Leadership with a Coaching Concentration from Northeastern University. I’m also on faculty in the Entrepreneurship Division at Babson College, teaching Entrepreneurship in Fashion, Organizational Entrepreneurship, and Fashion and Influencer Brands to audiences from high school through executive education. My teaching has also included the Boston College Business & Leadership Institute, where I taught leadership, design thinking, and strengths-based development. I’ve been a guest lecturer at Boston College, Boston University, Bentley University, and Hult International Business School.

Speaking & Thought Leadership

For nearly 20 years, I’ve spoken at business and university conferences across the country, as both keynote speaker and panelist. Most recently, I delivered the keynote “Humans in the Loop” at eTail Connect West and moderated its panel on building the AI-ready organization. Past stages include eTail East, the Massachusetts Conference for Women, where I spoke on “Authentic is the New Perfect,” and conferences at George Washington University, Boston University, Harvard University, and Hult International Business School. My talks focus on people-first leadership, especially the human side of AI: how leaders prepare their teams for change, build on their strengths, and keep human judgment at the center of the work. I also speak on omnichannel strategy and retail innovation.

Executive Background

For over 35 years, I've led merchandising and eCommerce organizations across global and founder-led brands including The May Company, Harley-Davidson Motor Company, PUMA, ALEX AND ANI, J.Jill, and Talbots — consistently being the one tapped to launch new, intrapreneurial ventures inside those organizations.

Featured in

Building People-First Ecommerce Teams

An in-depth interview on servant leadership, strengths-based team building, and why human judgment still matters in an increasingly data-driven, AI-enabled world.

The Strength of Authenticity

A recent interview exploring how authenticity shapes the way I lead, connect, and build trust with teams.

Graduate Spotlight

A reflection on what earning my Master’s in Organizational Leadership and Coaching revealed about leading with purpose.

eTail East

Highlights from my recent conference session on the benefits of uniting physical and digital retail to build lasting, community-centered customer experiences.

Watch: Organizational Entrepreneurship — Babson College

A look inside the Organizational Entrepreneurship course at Babson, where I teach the next generation of leaders how to apply real-world entrepreneurial thinking inside organizations.

Have Questions?

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