DSG Global (Diversified Search Group) Appoints Co-Leaders of Chicago Office
April 24, 2025 – DSG Global (Diversified Search Group) has named Margaret Resce Milkint and Cheryl Stevens as co-leaders of the firm’s Chicago office. The announcement underscores DSG Global’s ongoing commitment to growth in the Chicago market and throughout the Midwest, serving clients locally, nationally, and worldwide. “We are thrilled that Margaret and Cheryl will be co-leading our Chicago office, bringing with them deep leadership, expertise, and having meaningful impact across all sectors,” said Aileen K. Alexander, CEO of DSG Global. “As we continue to expand our reach, their partnership will continue to fortify our presence in the Midwest and accelerate our ability to enable exceptional outcomes for our clients.”
Ms. Milkint, who joined DSG in 2021, serves as managing director and global insurance practice leader within the firm’s financial services practice. With over 35 years of experience in executive search, has serves the insurance and healthcare sectors. Her expertise spans C-suite and board searches, succession planning, and transformational leadership initiatives across the property and casualty, life, health, and reinsurance sectors.
Ms. Stevens is a managing director in DSG’s non-profit & social impact practice. Since joining the firm in 2018, she has earned a reputation for placing senior executives in a wide range of mission-driven organizations across the non-profit, philanthropic, and broader social enterprise sectors. Known for her relationship-centered and values-driven approach, Ms. Stevens leads CEO and senior leadership searches in Chicago and nationwide.
As co-leaders of the Chicago office, Ms. Milkint and Ms. Stevens will work collaboratively across practices and industry sectors to build on the firm’s foundation in the region, enhance client relationships, and identify opportunities for growth and innovation.
“Chicago is a hub of growth and intersection for DSG Global from our practices in non-profit & social impact to insurance & financial services, education, and healthcare,” said Ms. Milkint. “We are ready to build our synergies and accelerate DSG Global’s impact on the Windy City. I am excited to collaborate with my trusted partner, Cheryl Stevens, and our winning Chicago colleagues.”
“I joined Koya seven years ago, and it’s been incredible to see how we’ve grown-now as part of DSG Global-to expand our reach and deepen our impact,” said Ms. Stevens. “Chicago and the Midwest have been key markets throughout my time with the firm, and it’s an honor to step into this role alongside my colleague Margaret, building on such a strong foundation as we continue to grow and strengthen our capabilities.”
Related: Storbeck Search | DSG Global Names Practice Leader for Education Practice
DSG is a family of firms serving specialized sectors. The firm was founded almost five decades ago for the express purpose of placing diverse candidates in client organizations. Koya Partners is a part of DSG and is dedicated to mission-driven leadership. Koya works broadly at the senior-most levels of the mission-driven field in philanthropy, social services, arts and culture, and social justice, among others.
New CFO
DSG recently appointed Rob Alessandrini as its new chief financial officer. “We are thrilled to welcome Rob to our team,” said Ms. Alexander. “His depth of finance experience in growth environments, strategic insight, and commitment to driving results will be invaluable as we continue to scale our organization and support our clients. Rob’s leadership will help us continue our growth trajectory and remain strategically agile in achieving our mission to make a positive impact on the future of leadership.”
Leading and Scaling with Talent
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“Rob’s impressive career is defined by his ability to balance financial acumen with strategic vision,” said Steve Morreale, chief operating officer of Diversified Search Group. “His proven track record in driving results, combined with his collaborative approach, makes him the ideal partner to help lead DSG into its next chapter of growth.”
Mr. Alessandrini brings significant financial leadership experience to DSG, including a track record in corporate finance, strategic planning, and investment management. He joins DSG following a tenure as CFO at The Judge Group, a staffing, training, and business solutions company. During his time there, he played a pivotal role in driving growth and operational excellence. His earlier experience includes key roles as an international equity analyst at DuPont Capital Management and as a financial analyst at The Vanguard Group, where he gained experience in financial modeling and investment strategies.
Related: Diversified Search Group Appoints CEO
Contributed by Scott A. Scanlon, Editor-in-Chief; Dale M. Zupsansky, Executive Editor – Hunt Scanlon Media
