Leading in Stilettos

Nathalie Gregg head shot
Nathalie Gregg
Leading in Stilettos

Location: Columbia, South Carolina

Founded: 2013


FastTrac® GrowthVenture™  - Graduated 2008

Affiliate: Midlands Technical College

Build the concept. Leading in Stilettos is dedicated to empowering and inspiring women with concrete strategies and tactics that help them maintain their femininity while achieving their goals, particularly in largely male-dominated arenas. Spurred on by Gregg’s “battle cry” for all women ‑ #LeadLoudly — the company develops products, programs and seminars that help entrepreneurs and professionals get clients, build businesses, and accelerate their personal and professional growth. 

Plan the strategy. Even as a small child, when her father invited her to visit a business boardroom, Gregg noticed she was the only female there. Virtually ever since, she has dedicated herself to helping women crack the glass ceiling in boardrooms and other business environments that, even today, remain largely dominated by men. Gregg consults, trains, coaches and mentors women across the country who desire to advance into leadership roles and sharpen their personal leadership capabilities. 

Grow the revenue. Based on her experience as a leadership consultant — and on her studies and research as a student at Columbia College, at the Kenan-Flagler Business School of the University of North Carolina Chapel Hill’s Executive Management Program and with FastTrac — Gregg codified her approach to female empowerment by writing and marketing a book, which also is titled “Leading in Stilettos.” She uses the book, workshops, seminars and speaking engagements to promote the Leading in Stilettos philosophy and services, and also completed a 10-city social media tour to get women talking and taking action about leadership and its challenges. She has continued to use social media to share “Monday Motivation” and a “Tuesday Tech Tip,” which lift up female role models who lead and dream big. Leading in Stilettos got an additional boost when Gregg was recognized with the Columbia College President’s Award and the prestigious ATHENA Award (link:, and was featured on the cover of Columbia Business Monthly as “A Woman Who Leads.”

Expand the market. Gregg says expanding her network, her strategic business partnerships and her reputation as a leader will, in turn, expand the Leading in Stilettos philosophy and reach. That’s why she serves on several executive boards, including the Greater Columbia Chamber of Commerce, Leadership Columbia and the South Carolina Association of Community Development Corporations. To reach the next generation of leaders, she also has become involved with Junior Achievement and serves as the host of Junior Achievement’s nationally televised show.

Insight/Hindsight. “FastTrac helped me learn how I can build Leading in Stilettos through strategic partnerships, by restructuring my business model and by sharpening my brand message. The opportunity to stay in touch with other Charleston-area FastTrac graduates and connect with FastTrac alumni nationally will support my continued success.