T.R. Jennings

T.R. Jennings has spent her career in the space between strategy and execution. For more than fifteen years she has worked beside presidents, CEOs, and executive teams in healthcare technology, financial services, research, government, and the nonprofit sector, learning how leaders think, where organizations lose momentum, and what it takes to keep the two connected.

Her foundation was built in federal operations, where she led a large team through shifting policy priorities and wrote on the agency’s behalf to audiences around the world. That work taught her two things she still relies on: precision matters most when the stakes are high, and the people closest to the work usually know what’s broken before anyone at the top does.

Over the following decade, she partnered with C-suite leaders across the full executive agenda: preparing boards, shaping leadership communications, planning for business continuity, and turning intent into action across global teams.

Today, as a Chief of Staff, she is building the function, and much of an organization’s operating infrastructure, from the ground up. She designed the cadence that keeps its leadership aligned, guided succession planning through leadership transitions, rebuilt how the organization reviews and rewards its people, and strengthened the policies that protect it. Where there is no playbook, she writes one.

T.R. works as an embedded partner. She spends time with the people doing the work, brings leaders an honest picture of what is and isn’t moving, and builds structure light enough to keep pace with the organization.

T.R. holds an MBA with a concentration in human resources and a master’s in educational leadership, both reflecting a long interest in how organizations develop their people. She is carrying that interest into a PhD in leadership and organizational theory. She is also completing Harvard Business School’s Chief of Staff executive education program, holds a certificate in women in leadership from Cornell University, and is a member of the Chief of Staff Association, the Chief of Staff Network, and the Project Management Institute.

Outside her work, she is a marathoner, a writer, a world traveler, and a lifelong advocate for the natural world.

Research & Writing

Alongside her consulting work, T.R. writes on leadership and how organizations work. Essays and research will be published here.