Cindy Jacobs
Client Services Associate
As a Client Service Associate, Cindy Jacobs is an integral part of VestGen. Cindy grew up in the Dundee area and currently lives in St. Charles. After graduating from college, her first job was with a financial firm where she received her first introduction into the finance world as a sales assistant and also as a wire operator sending trades to the floor. After taking years off to raise her two sons, John Connor and Carson, she returned to the workforce and joined Keith and Joe’s team in November of 2010. Cindy manages the move money requests, prepares the reports for upcoming client reviews, and oversees the case notes after the reviews. She is also the first point of contact for new clients onboarding.
In her spare time, Cindy enjoys the outdoors by walking, hiking, biking, canoeing, and staying active. She also likes to travel, try local cuisines, and listen to live music. Cindy graduated with an Associate of Arts in Business Administration and Management from Robert Morris College.
Josh Gerry
Chief Executive Officer
Josh Gerry is redefining succession planning for wealth advisors.
Widely recognized as one of the industry’s leading voices on advisor succession, Josh Gerry is CEO of VestGen Wealth Partners and a 2025 Luminaries Finalist in the M&A Leader of the Year category. He spearheaded the unprecedented merger of 10 advisory practices in December 2024 to launch VestGen, creating a fully integrated wealth management firm that empowers advisors to transition with confidence and aims to ensure clients’ continuity of care across generations. His leadership was recently profiled in a full-page InvestmentNews feature, “Seeking Success from Succession.”
With more than three decades in wealth management, Josh brings deep experience in succession, M&A, and growth strategy. Prior to VestGen, he co-founded Professional Wealth Advisors, LLC, where he scaled the firm to over $10 billion in assets while guiding advisors through successful practice transitions. He later served as CEO of Impetus Wealth Strategies, securing capital commitments to fuel advisor succession and expansion. His earlier leadership roles at AXA and MetLife gave him a deep understanding of large-scale advisor transitions across enterprise firms.
At VestGen, Josh leads the firm’s mission to solve one of the industry’s most pressing challenges: the $13 trillion in assets expected to transition as nearly 40% of advisors retire in the next decade. Josh brings both credibility and conviction to building the next generation of advisor leadership. He is a frequent speaker at industry conferences and contributes thought leadership on the future of succession planning and advisor M&A.
Josh holds a B.S. in Business Economics from UCLA.