As Principal of Investments & Advisory, Montgomery brings institutional-grade analytical discipline to Oak Valley Capital's investment process and advisory practice, serving as the senior bridge between the firm’s analyst team and CIO-level decision making. In this role, he is responsible for underwriting quality assurance, value creation planning, and day-to-day oversight of the analyst team. Montgomery ensures that every financial model, deal structure, and investment committee deliverable meets the institutional standards required to compete and execute in the lower middle market.

Prior to joining Oak Valley Capital, Montgomery spent three years at Trinity Capital underwriting debt facilities to venture-backed, growth-stage technology companies — developing deep expertise in credit analysis, leverage feasibility, and institutional underwriting methodology across complex capital structures. Earlier in his career, he worked at Chronograph, where he partnered with large LPs and GPs to monitor and track their investment portfolios through Chronograph's platform, gaining exposure to how sophisticated institutional investors evaluate and manage diversified alternative asset portfolios.

Outside of work, Montgomery is passionate about strength training, experimenting with new recipes, and spending time outdoors with family and friends.