Men To Watch 2025 honoree Dr. Jermaine Wilson

Dr. Jermaine Wilson is a nationally acclaimed leadership strategist, executive coach, and founder of Pivot Path Strategic Solutions—a consulting firm dedicated to helping executives, organizations, and teams navigate complexity with clarity and purpose. With over 20 years of experience in public education leadership, strategic facilitation, and executive coaching, Dr. Wilson is known for empowering leaders to make bold decisions, strengthen organizational alignment, and accelerate measurable results. His deep commitment to fostering inclusive environments and championing leadership has been a cornerstone of his work.

Dr. Wilson’s expertise in designing tailored development programs has enabled countless leaders to harness their potential and drive meaningful change within their organizations. His passion for lifelong learning is evident in his collaborative workshops and seminars, where he seamlessly integrates cutting-edge research with practical applications. Through his engaging and dynamic approach, Dr. Wilson inspires and equips leaders with the tools necessary to thrive in today’s ever-evolving landscape.

Specializing in strategic planning and organizational development, he has successfully guided senior leaders and executive teams through transformative initiatives across corporate, nonprofit, education, and government sectors. His approach blends results-driven coaching with practical, research-informed frameworks. Clients consistently report 25–40% improvements in strategic execution, leadership effectiveness, and cross-functional collaboration within the first year. He has helped executives exceed profit targets, align culture with strategy, and unlock new pathways for growth.

Jermaine is the creator of the Leadership in Times of Change series and the architect behind powerful tools such as the Resilient Leader Framework and the 4C Clarity Filter—resources widely used by leaders to navigate uncertainty, make values-aligned decisions, and cultivate high-performing, resilient cultures. Whether facilitating long-term strategy or supporting executive transitions, he brings a unique blend of systems thinking, emotional intelligence, and strategic clarity.

Jermaine is a healing-centered leader in the coaching realm and serves as an Assistant Superintendent in the public education sector. He is passionately dedicated to guiding organizations towards purposeful and high-performing leadership. His methodology is rooted in empathy, data-supported, and enriched by his Ph.D. in Leadership, Policy Studies, and Curriculum and Instruction. A regular speaker at national conferences, Jermaine is a recognized authority in equity-centered strategies, adaptive leadership, and navigating decision-making within complex environments.

At the core of his work is a powerful belief: every leader faces pivotal moments—turning points that demand clarity, courage, and decisive action. Through coaching, facilitation, and strategic thought partnership, Jermaine equips leaders to rise to those moments with confidence and conviction.