Leadership - UpSurge Baltimore

Jamie McDonald

CEO

Jamie McDonald is CEO of UpSurge. Jamie is an experienced entrepreneur, movement builder, and speaker. Prior to joining UpSurge, she was an advisor to global entrepreneurs, social innovators, and impact-focused executives. She’s been deeply involved in work on behalf of Baltimore throughout her career.

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Kory Bailey

Chief Ecosystem & Relationship Officer

A native of Durham, North Carolina, Kory Bailey is a natural community builder, adept at cultivating and leveraging relationships for collective benefit. Experienced in tech sales and leadership for both large companies and startups, Kory brings a win-win perspective to his work. Kory leads UpSurge’s efforts with entrepreneurs and investors, connecting dots, identifying opportunities and breaking down barriers to help facilitate growth.

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Madeleine “Maddy” Stokes

Chief Operating Officer

Maddy oversees the UpSurge team and organization, including finance and growth, legal, people operations, program strategy and evaluation. Maddy started her career in international development, working in Beirut, Lebanon supporting civil society organizations and activists. She later spent four years helping Johns Hopkins Technology Ventures build a dynamic entrepreneurship community. Serving on the boards of the Baltimore Museum of Industry and B-360 Baltimore, Maddy brings her community development lens, good trouble attitude, and love of people into everything she does.

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Naomi Winston

Marketing and Communications Analyst

Naomi graduated from Xavier University of Louisiana with a degree in History in May of 2021. After displaying a deep passion for entrepreneurship, she applied for Venture for America where she was accepted as a member of the 2022 class. Through her company Revolutionary Hearts Ind. she dove head first into learning about marketing, web design, and graphic design. This led to her role as the Marketing and Communications Analyst for UpSurge Baltimore. Naomi is hoping to take the opportunity in Baltimore to experience the deep culture, community, and history that lie within the streets of Charm City.

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Chris Bunner

Data Analyst

As Data Analyst, Chris focuses on UpSurge’s reports and internal data systems. Chris, a suburban Atlanta native, graduated from Boston College in 2022 with a BS in Management, a major in Economics, and a minor in Social Impact. As a Venture for America ‘22 fellow, Chris is excited to learn from and support Baltimore’s growing entrepreneurial ecosystem.

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Dazia Wallerson

Administrative and Database Coordinator

Dazia Wallerson is a compassionate and experienced human service professional leveraging operational, managerial, and nonprofit experience to enhance the development of individuals, organizations, and thriving communities. Driven by her background in systems-thinking, she takes pride in providing the most efficient and effective strategies to help ecosystems grow. Dazia champions diversity, empathy, and connection to energize culture and inform creativity and innovation. She leads administrative and database functions for UpSurge.

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UpSurge Contractors

UpSurge is grateful to work with a set of mission-aligned, Baltimore-based contractors providing expertise across finance, accounting, operations, marketing, and communications.