Jay Hennessy

Jay Hennessy brings over 25 years of experience growing and leading businesses to his role as Business Growth Advisor at Stringfellow Technology Group. As a former entrepreneur and executive, Jay understands firsthand the challenges leaders face when technology becomes a barrier instead of a driver for growth .

Before joining Stringfellow, Jay founded and scaled a legal technology firm that achieved double-digit annual growth and expanded to five regional offices before acquisition. He later served as Vice President of Business Development for Juris, where he built strategic partnerships and drove nationwide sales expansion. His career has also included founding a fitness and wellness business, giving him a unique perspective on how technology supports both operational excellence and customer experience .

At Stringfellow, Jay partners with CEOs, CFOs, and operations leaders to align IT strategy with business objectives. He helps companies outgrow legacy systems, strengthen performance, and gain the confidence that comes from predictable, well-managed technology.

Business leaders value Jay’s depth of experience, straight-forward communication, and results-driven mindset. His focus is simple: help organizations achieve their next stage of growth through smart, reliable IT.