OUR LEADERSHIP TEAM
Stephanie Terry
Executive Director and Co-Founder
Rinnie Orr
Associate Director and Co-Founder
Joseph Holmes
Communications Liaison Americorp VISTA
- Stephanie Terry | (Executive Director & Co-Founder)
Stephanie is a visionary leader driving WEBB Squared’s mission to empower Black entrepreneurs. With a background in community organizing and corporate strategy, she fosters individual success while strengthening communities.
- Rinnie Orr | (Associate Director & Co-Founder)
Rinnie leads WEBB’s mindset and coaching initiatives, ensuring smooth program operations. As a trained coach, she inspires transformation and supports entrepreneurs in reaching their full potential.
- Joseph Holmes | (Communications Liaison, AmeriCorps VISTA)
Joseph strengthens collaboration across WEBB, supporting entrepreneurs and BIPOC business partners. With expertise in community outreach and coaching, he plays a key role in the Chatham County Innovation Lab.
OUR BOARD OF DIRECTORS
Maxine Burgess
Board Chair
Carol Hewitt
Board Co-Chair
Evan Springfield-Cobb
Board Treasurer
Judy Batista
Board Secretary
Bobby Duke
Board Member
WEBB Squared is led by a diverse board of community leaders dedicated to advancing equity through small business economic development.
- Maxine Burgess (Chair) – CEO of Binsured Advisors LLC, author, and insurance producer focused on empowering individuals with healthcare and financial solutions. She also serves in leadership roles with the Sanford Professional Women and Greater Greensboro Black Chamber of Commerce.
- Carol Hewitt (Co-chair) – Founder of Slow Money NC, providing affordable loans to sustainable farmers and food entrepreneurs. She is also the author of Financing Our Foodshed.
- Evan Springfield-Cobb (Treasurer) – Financial Advisor at Edward Jones and founding member of WEBB Squared, passionate about financial education and entrepreneurship.
- Judy Batista (Secretary) – Speech-language pathologist, founder of Laughing Monitos, and advocate for racial equity and small business growth.
- Bobby Duke – Community builder, engagement consultant, and leader in inclusive coworking spaces, committed to supporting local businesses and equitable communities.
OUR CONSULTANTS
James Monte & Wonza Montague
Commercial Development Consultant
Dr. Carolyn Jefferson-
Program Consultant
Lynn
Development Consultant
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James “Monte” & Wonza Montague (Commercial Development Consultants) – Founders of F7 International Development, a community development corporation focused on affordable housing and commercial investments in underserved areas of Raleigh. Their projects include Elder’s Peak, Falcon’s Point, Montague Square, and F7 Blackstone Ranch.
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Dr. Carolyn Jefferson-Jenkins (Program Consultant) – Internationally respected educator, author, and speaker with a 50-year career in civil rights, voting rights, African-American history, and racial equity. She has also served as an adjunct assistant professor at UNC.
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Lynn (Development Consultant) – A fundraising and grant-writing expert with over 20 years of experience in program management, resource development, and administration across government, university, and nonprofit sectors.
Annual Reports and Strategic Plan
At WEBB Squared, we are committed to transparency, growth, and impact. Our annual reports highlight key milestones, achievements, and the progress we’ve made in empowering Black entrepreneurs. Explore our strategic plan to see how we are shaping the future of wealth creation and economic equity.
