Chief Strategist
Jess B Enterprises LLC

Jessica Gibson-Brokenbaugh is a visionary community development leader with over 25 years of experience driving transformative change across Delaware through strategic program development, grant writing, and multi-sector partnership building. A TEDx speaker (“The Diamond Polisher Revealed”) and sought-after thought leader, she brings powerful insights on entrepreneurial development, business growth, and ecosystem building to audiences nationwide. From the Bronx to the boardroom, she has led multi-million-dollar initiatives, pioneered first-of-their-kind programs, and earned a day named in her honor in New Castle County, Delaware.

A strategic development and capacity-building consultancy where Jessica provides technical assistance, nonprofit capacity building, and programmatic solutions that drive community growth and economic impact. From facilitating millions in capital access for women business owners to designing strategic plans that strengthen organizations from the inside out, she delivers results across entrepreneurial ecosystems, nonprofit leadership, and community engagement. A dynamic speaker and facilitator, Jessica brings the same transformational energy to the stage — equipping audiences with actionable strategies for intentional growth, resilient leadership, and sustainable change.

Deep Dive Inc. | Founder

A comprehensive entrepreneurial wellness program, addressing the critical gap where 87.7% of entrepreneurs struggle with behavioral health burn out challenges impacting business performance. The goal is simple, guide entrepreneurs to get time back to focus on building profit. This year-round initiative integrates behavioral health, AI-powered business development training, emotional intelligence coaching, and sustainable peer support networks through five annual events.