Josh Kaplan, a CFA Charterholder, leads sunset portfolio strategy, reporting and investment operations at Gary Community Ventures, while contributing to the organization’s impact investing initiatives.

He brings over a decade of experience in investment operations, research and compliance. Most recently, as Chief Compliance Officer & VP of Advisory Services at Landmark Wealth Management, Josh led portfolio strategy, investment research and risk analysis. He spearheaded compliance initiatives, guiding the firm through SEC audits, and drove operational efficiencies through strategic technology integration.

Beyond his technical expertise, Josh has worked extensively with high-net-worth individuals, investment committees, boards, nonprofits and government entities, developing a deep expertise and understanding of asset management across diverse audiences.

Driven by a passion for community impact, Josh made a deliberate career pivot — taking a sabbatical to explore U.S. national parks, the Pacific Northwest and Europe — before channeling his financial expertise into mission-driven work.

A dedicated Buffalo Bills fan, Josh enjoys hiking, skiing, trivia, and traveling to see his family members who are spread across the U.S. and Canada.