Meet The Leaders Behind The Deeper Dive
Where mental wellness meets business excellence. Our leadership team is dedicated to redefining entrepreneurship—one balanced, resilient, and visionary leader at a time.
Our team
ENTREPRENEURSHIP DEVELOPMENT
Jess Gibson Brokenbaugh, Founder
Jessica Gibson Brokenbaugh is a holistic entrepreneurial development expert and founder of Jess B. Enterprises, with a proven legacy of empowering business growth and financial resilience. As the founding director of the Women’s Business Center at First State Community Loan Fund (now True Access Capital), she pioneered programs that reduced loan risk, strengthened borrower success, and secured federal approval for one of the nation’s leading Women’s Business Centers. Her work continues to champion entrepreneurship, equity, and sustainable business development.
GLOBAL ORGANIZATIONAL STRATEGY, SENIOR LEADERSHIP
Dr. Lenny Howard, Ed.D
Dr. Lenny Howard is a Senior Leadership Coach and Global Organizational Strategist with over two decades of experience driving transformative leadership and organizational excellence. As the force behind multi-million-dollar coaching contracts through Pathways 2 Careers, he empowers leaders and institutions to build trauma-informed, emotionally intelligent, and inclusive systems. A recognized expert in Diversity, Equity, Inclusion, Accessibility, and Belonging (DEIAB), Dr. Howard has led initiatives such as a $5.1M National Institute of Justice Grant focused on coping strategies and served as Chief of Staff overseeing a $50M Target Investment Zone Initiative. His work blends data-driven strategy with a human-centered approach to foster sustainable growth, wellness, and equity across organizations worldwide.
BRAND DEVELOPMENT, STRATEGY CONSULTANT
Michelle Washington
Michelle Washington is a seasoned Brand Development Expert and Strategic Consultant dedicated to transforming personal and business brands from concept to impact. With a focus on authenticity, clarity, and strategy, she helps entrepreneurs develop cohesive brand identities that connect deeply with their audiences. Through her comprehensive approach to brand strategy and development, Michelle empowers leaders to elevate their presence, refine their message, and position their brands for lasting success.
DIGITAL MARKETING, BRAND STRATEGY, AI- AUTOMATION
Armance’ Jones
Armance’ Jones is a digital marketing expert, brand strategist, and product developer with over 13 years of experience building and scaling fashion, beauty, lifestyle, and tech brands. As the founder of Armance’ Digital, she helps businesses grow with style, systems, and strategy—creating integrated campaigns, AI-powered marketing flows, and customer-focused growth plans. With a proven track record in product innovation, e-commerce, and brand development, Armance’ is known for turning bold ideas into high-performing brands that connect content, commerce, and community.