Big Oaks Ventures was founded on the belief that the best growth strategies are shaped by experience, not theory.

Over the past two decades, Shane O’Donnell has worked at the center of recruiting, HR technology, and workplace innovation, helping companies navigate the challenges that come with scaling. From helping grow a staffing business to $90M and a successful exit, to contributing to the rise of Indeed ahead of its $1B+ acquisition, to scaling Recruitics more than 10x, his career has been defined by building through complexity, but handling it head-on.

Along the way, he saw a consistent pattern: as companies grow, decisions become harder, stakes increase, and alignment across leadership becomes more difficult and even more critical.

Big Oaks Ventures was created to bring that hard-earned perspective to founders, executives, and senior leaders facing those key moments by providing clarity, discipline, and trusted guidance when it matters most.

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