AJ Montgomery

As a Managing Partner, AJ Montgomery is focused on building relationships with financial advisors and investment professionals and supporting the distribution of investment solutions designed to address the evolving needs of their clients. His approach emphasizes understanding each advisor’s practice, identifying appropriate investment opportunities, and developing long-term partnerships grounded in responsiveness, transparency, and disciplined execution.

AJ brings more than 15 years of experience in the investment management and financial services industry, with a background spanning asset management distribution, custom portfolio solutions, and relationship management within the Registered Investment Advisor marketplace. Prior to joining a-Squared Investment Partners, AJ spent several years with an institutional asset manager, where he served the Midwest RIA market and worked closely with financial advisors to provide custom asset management solutions. His experience included helping advisors evaluate portfolio strategies, develop customized investment allocations, and implement solutions designed around the specific objectives of their clients.

Throughout his career, AJ has worked closely with financial advisors, portfolio management teams, and investment professionals to translate sophisticated investment strategies into practical solutions for advisors and their clients. His experience across both investment management and distribution has provided him with a broad understanding of the challenges advisors face when constructing portfolios, differentiating their practices, and delivering customized investment solutions.

Known for his relationship-driven approach, AJ places an emphasis on understanding the individual needs of the advisors he works with rather than taking a one-size-fits-all approach to investment solutions. His philosophy is centered on long-term partnership, clear communication, and helping financial professionals identify investment strategies that align with the objectives of their clients in an increasingly complex market environment.