Raymond Gleason

CEO Mentor

Raymond Gleason brings more than 30 years of entrepreneurial success, leadership, and 10,000+ coaching hours to Building Champions and his clients.

Raymond’s background includes marketing, sales, engineering, equity investing, and technology. He founded and sold two companies, led a 3rd company to go out of business, created university curriculum, taught at several universities, and co-authored a business book. He predominantly works with executives and business owners, coaching and mentoring them utilizing a contrarian style of thinking.

His business career began in marketing and sales for a national engineering company, later becoming their director of marketing. At the age of 27, after realizing that he wanted to own, risk and direct, Raymond became a business owner. He found himself responsible for over 120 lives (employees) and very quickly understood his need for key mentors in both his work and life. This realization provided the basis for many years later to serve as mentor and coach.

Over the span of twenty years, Raymond co-founded and served as CEO of both an engineering company and technology services company, both achieving impressive revenue in less than five years. In 1986, his first company was awarded the SBA’s Administrator’s Award for Excellence.

Between the two companies, Raymond took a “hiatus” to combine two of his loves: living in the Pacific Northwest and teaching. He became a university professor, teaching coursework in both undergraduate and graduate business schools, as well as serving on the curriculum team to design the MBA program. In 1997, Raymond was the recipient of George Fox University’s Outstanding Professor award, citing his unique style of having students ad hoc stand-up and debate ideas with him in the classroom. Later, he served as Executive-in-Residence before going back into the business world.

In 1994, he co-authored the book “Confessions of Empowering Organizations” (AQP: 1994), which documented the most innovative workplace practices in over 90 Pacific Northwest companies.

He has served and continues to serve on a variety of boards in the following industries: oil & gas, financial services, data centers, software, supply chain, retail, hospitality, petroleum, and telecommunications. From 1980 through 2018 Raymond was an owner/principal investor in a privately held firm focusing on both equity and angel investing (where he and his partners focused exclusively on formative stage investing).

In 2018 Raymond became a Principal Advisor to a Single Family Office (SFO).

Raymond joined the Building Champions team in 2002. His executive mentoring practice focuses upon three types of clients: Business Owners, C-Suite, and “NextGen” leaders. The range of companies he serves covers numerous industries and size, ranging from a privately held $2.5M to publicly traded, $390B market cap. He also works with his executive and owner clients to understand, appreciate, and create meaningful and effective boards (both advisory and director).

Grounded in his belief, he coaches clients to develop their inherent ability and motivation to master contrarian thinking. Raymond’s coaching mantra and goal for a client to achieve is: “The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function” (F. Scott Fitzgerald).

With an eclectic range of interests and pursuits, Raymond is a voracious reader. With “age” has come the taking of more time and enjoyment of deepening relationships, small group getaways to discuss areas of human behavior, economics, great works of fiction, and Christian mystics (e.g., Julian of Norwich, Bernard of Clairvaux, Simone Weil). And while not a mystic, he enjoys the writings and movies of Bill Murray, too.

“My executive coach has stretched my thinking continuously for the last six years. He often challenges my comfort zones, therefore allowing me to really grow as a leader in life and work. Not only has he made a memorable and measurable difference in my life; he’s done the same for multiple members of our team.”
Ryan Wall, CEO, FHI

  • Executive Leadership
  • Mergers & Acquisitions
  • Strategic Thinking & Planning
  • Family Business & Succession Planning
  • Board Creation & Consulting
  • CEO Mentor
  • Executive Retreats