Meet our Founder and CEO — Jessyca Dudley

We’re excited to re-introduce our Founder and CEO, Jessyca. With extensive experience as a social sector leader and strategic advisor, Jessyca has guided individuals and organizations to implement strategies that advance racial equity. Her leadership spans impactful roles, including advocating for BIPOC communities and building equity-centered initiatives. At Bold Ventures, Jessyca fosters trusting relationships with clients and leads efforts that create meaningful, community-centered change.

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Jessyca Dudley (she/her) is an experienced social sector leader and strategic advisor who has supported individuals and organizations to shape their strategy, implementation, and learning to advance racial equity.

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As the founder and CEO of Bold Ventures, she leads a dynamic team and develops strong and trusting relationships with clients through facilitation and stakeholder engagement that enhances the impact of their efforts.

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Jessyca’s prior leadership roles include serving as the Executive Director of Chicago African Americans in Philanthropy, as a Director at Arabella Advisors where she developed new strategy approaches and advocated for investment in BIPOC communities, and as the Gun Violence Prevention program officer for the Joyce Foundation.

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We asked Jessyca a few questions to get to know her better.

Why are you passionate about advancing community–aligned and impactful giving?

Born and raised in Chicago, I have seen first hand how philanthropy has often excluded communities and their perspectives. I have been on both sides of the system — seeking funding and making grants — and have seen how the opaque practices of philanthropy are used to regulate access to funding for BIPOC communities. It’s critical that more people understand and engage with philanthropy if we are going to shift this system towards equity. It will take bold action and bold leadership from each of us to change the system.

By moving resources to communities of color, what kind of world do you hope to see?

I envision a just world where BIPOC people and communities have the power of self-determination, the resources, and autonomy to dream into life new ways of being that bring an end to extractive practices and create a society of belonging and inclusion for all.

How are you living the value of mutual respect?

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By valuing all people for who they are and what they bring to the table. Through this practice we are able to recognize and understand differences, and ensure that these perspectives contribute to our work.

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What is your passion project or hobby outside of work?

Taking part in new experiences with friends and family — many of which involve food.

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Articles published by Bold Ventures:

Announcing All Together Bold

Planning Your Year-End Giving: Reconnecting with Your Values and Prioritizing Equity in 2025

Reflecting on Four Years

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We’re excited about the expertise and support Jessyca brings to our team, and we look forward to the opportunity to assist you further.