Women’s Leadership and Race

“The Self-Aware Leader: Understanding How Race Affects Your Leadership”                                      for women of color and white women

Have you examined the relationship between being a woman in leadership and race? When was the last time you gathered with other women and femmes to discuss how an awareness of race and power impacts your leadership?

This 12-week intensive will ask for your vulnerability and humility as Jacki and Jessyca lead discussions that center on how these factors affect your assumptions about yourself and your power, and how to consciously engage in developing your potential and power.

The next cohort begins this fall.

Below is the curriculum for the group sessions. The cohort sessions for women of color and white women will be led individually by Jessyca and Jacki, respectively, and be responsive to each group members’ experiences and individual goals.


  • Session 1: Leadership assessment and articulation of each person’s goals 
  • Session 2: Affinity Group
  • Session 3: Engagement and authenticity 
  • Session 4: Affinity Group
  • Session 5: Contested authority 
  • Session 6: Affinity Group
  • Session 7: Understanding the role of race in our leadership story
  • Session 8: Affinity Group
  • Session 9: Leadership models and frameworks
  • Session 10: Affinity Group
  • Session 11: Leadership commitments
  • Session 12: Self-Reflection and Sharing

Program fee: $1,500.

If interested, please apply here.

For any questions, reach out to Jacki Davidoff (jacki@davidoffstrategy.com) or Jessyca Dudley (jessyca@alltogetherbold.com)



Jacki Davidoff

Principal, Davidoff Strategy, Executive Leadership Coach

Jacki is a management and human capital consultant who designs and leads consulting, training, and facilitation processes with management teams, Boards, staff, and individuals to identify the next level of their growth and development. This supports teams and individuals to break through silos and internal barriers that keep them static.

Davidoff’s clients include American College of Preventive Medicine, Christopher Family Foundation, deBeaumont Foundation, Duke University School of Family and Community Medicine, National Association of Chronic Disease Directors, News Literacy Project, Planned Parenthood Federation of America, and Public Narrative.

Jacki is also executive leadership coach to executives across the country, with particular focus on women leaders/women leaders of color. Jacki is founder and facilitator of three leadership development groups for diverse women: the Leadership Forum for nonprofit CEO’s and Executive Directors; the Leadership Forum, for women at all levels of leadership; and this new group co-facilitated with Jessyca Dudley: The Self Aware Leader: Understanding How Race Affects Your Leadership.

Additionally, Jacki’s background includes training congregations in the Unitarian Universalist Association to become anti-racist, multicultural congregations. Jacki serves as Board Co-Chair of Chicago Women in Philanthropy and is the former co-chair of the Racial Equity & Justice Committee. She is in the inaugural cohort of Chicago African Americans in Philanthropy’s Dismantling White Supremacy program. Jacki earned her BS in Advertising with the highest honors from the University of Illinois at Urbana-Champaign. Jacki completed her Masters in Transformational Leadership and Coaching at Wright Graduate University for the Realization of Human Potential in 2017.


Jessyca Dudley

Founder & CEO, Bold Ventures

 Jessyca brings an insightful, clear and strategic approach–supporting foundations and nonprofits committed to dismantling racism, sexism, and other forms of oppression. Jessyca is adept at developing strong and trusting relationships with clients through her excellent facilitation and stakeholder engagement skills, and works to develop strategies that enhance the impact of their efforts. Despite the challenges that accompany conversations about equity in philanthropy, Jessyca approaches those difficulties with patience, creativity, resolve, and the willingness to state a clear and well-grounded opinion and perspective.

Jessyca has more than two decades of experience working to transform and democratize philanthropy. Beginning as a volunteer at her church’s food bank, and later as the founder of the American Cancer Society’s youth board in Chicago, Jessyca officially began her career in philanthropy in 2013 as the Gun Violence Prevention program officer for the Joyce Foundation. In this role, she directed the program’s effort to address and reduce racial disparities by developing staff and grantee capacity to advance racial equity through the management of a $2 million portfolio of researchers and advocates.

Jessyca is currently the CEO of Bold Ventures and the director of Chicago African Americans in Philanthropy (CAAIP). In just 6 months as CAAIP’s executive director, Jessyca increased the organization’s membership by 30% and its fundraising revenues by 20%. 

Throughout her time in philanthropy, Jessyca has served as a Director at Arabella Advisors where she promoted dialogue, advocated for investment in BIPOC communities, and built infrastructure for equitable leadership roles in the social sector. She has held positions with the Lurie Children’s Hospital of Chicago, the University of Illinois at Chicago, and the University of Chicago. With these organizations, she has developed and implemented community-based prevention and outreach programs and conducted clinical and social science research to improve the health of communities in Chicago.