My Story

Gary A. Bolles is a highly accomplished professional with extensive experience in various domains, particularly in the realm of future work, career transitions, and event design. With his expertise and visionary approach, he has made significant contributions to the field.

Currently, Gary serves as the Chair for the Future of Work at Singularity University, a position he has held since August 2017. In this role, he leads Singularity University’s initiatives related to the transition to a digital work economy. He actively assists individuals, organizations, and government agencies in navigating disruptive changes and offers valuable insights as a frequent lecturer on the future of work and learning.

Since December 2012, Gary has been a partner at Charrette LLC, located in the San Francisco Bay Area. At Charrette, he specializes in strategic event design and production, collaborating with prestigious clients such as Google, Singularity University, London Business School, and L’Oreal. His expertise in creating impactful experiences through events has established him as a sought-after professional in this field.

In January 2012, Gary co-founded eParachute, Inc., a premier online resource catering to job-seekers, career changers, and entrepreneurs going through significant life and work transitions. As a co-founder, he has played a crucial role in providing guidance and support to individuals seeking new career paths and entrepreneurial opportunities.

Prior to his work at Singularity University, Charrette LLC, and eParachute, Inc., Gary served as the CEO of Xigi Solutions from December 2007 to January 2012. Xigi Inc. focused on building communities of impact through the use of software and events. Gary and his team developed custom online social networks and consulted on events that influenced markets and addressed global and local challenges. Notable clients included Google, Nokia, Skoll Foundation, London Business School, Deloitte, Sony, and The Hub/Bay Area.

In September 2004, Gary co-founded Microcast Communications, further showcasing his entrepreneurial drive and leadership skills. He also owned and operated CollectiveIntelligence.net from July 2002 to March 2005, contributing to the field of collective intelligence.

Gary’s expertise and insights extended to various roles throughout his career. He served as a contributing editor at CIO Insight from September 2002 to February 2004, providing valuable perspectives on technology and business. He also held the position of Chief Operating Officer at Evolve Software from 1996 to 1997, playing a crucial role in the company’s operations. Moreover, as the Editorial Director of Interactive Week at Ziff-Davis Publishing from 1994 to 1996, Gary made significant contributions to the publication. Additionally, he served as the Director of Training at TeleVideo Systems, Inc. from 1984 to 1986.

Gary A. Bolles’ diverse experiences and unwavering dedication to shaping the future of work and career transitions have made him a respected figure in his field. His expertise in event design, community building, and his commitment to empowering individuals and organizations have had a lasting impact on the way we approach work in the digital age.

Separated they live in Bookmarksgrove right at the coast of the Semantics, a large language ocean. A small river named Duden flows by their place and supplies it with the necessary regelialia.

Where I’ve Worked