About

Hilary Jane Grosskopf is a systems thinker and author. She has written multiple books, most notably Awake Leadership and Awake Ethics.

Hilary has always been drawn to improving systems and processes in a holistic way. She earned her degrees in Systems Engineering from the University of Pennsylvania and then spent her early career at large companies including Urban Outfitters (URBN) and Restoration Hardware (RH). Hilary took on roles ranging from managing warehouse moves, to building analytics and operations teams, and implementing financial systems and reporting solutions.

Throughout this experience, one thing above all else became clear: collaboration and leadership are often the most challenging parts of working in any organization. Despite having good intentions and a great product, the “people stuff” can be a major obstacle to progressing toward goals and enjoying the process. Individual behavior and team dynamics can make or break teams, careers, and companies.

And so, she thought, Could there be opportunity in this challenge? What if there were leadership systems and solutions for the “people stuff” that could make work and collaboration both more enjoyable and more productive?

In parallel with her work experience, Hilary began practicing and studying yoga in 2010. She was drawn to yoga for the holistic health benefits, but also because she found that many timeless aspects of yoga philosophy could be applied to improve her own behavior, mindset, and leadership at work. Hilary earned her 500-hour teaching certification from Yoga Tree in San Francisco in 2017. While systems engineering provided critical thinking skills, yoga provided the human-centered philosophy needed for solving the “people stuff” at work.   

Hilary designed her own systems and exercises for leading teams. Seeing the results, peers came to Hilary for advice on how to build more productive, inspired teams and retain people. This organic, in-real-time coaching experience became the foundation for Hilary’s two books, Awake Leadership and Awake Ethics. Her award-winning books contain systems for leadership paired with exercises for putting her guidance into daily practice at work.

Hilary founded her company, Awake Solutions, in 2017. What began as a contracting company for project management and analytics soon became a leadership business based on her two books and her viral exercise, Role Mapping. Hilary has coached executive leaders and has presented workshops for dozens of companies and organizations including LinkedIn, Stanford University, Scripps College, Augsburg University, Nicobar (India), Glassdoor, Baldwin School, Biggerplate, Women in Transportation, and more. She has been featured in Fast Company, The Economist, and Chief Executive.

Today, Hilary provides workshop services for organizations investing in leadership development and building thriving teams. Contact Hilary to learn more about her current remote and in-person programs.

Shop Now