Chris Jackson

I’m an entrepreneur, Air Force veteran, and retired Deloitte Consulting Managing Director with 30+ years of leadership, strategy, and emerging-technology experience serving private and public companies.

Over the past four decades, I’ve built and run businesses in construction, real estate, automotive, and technology, including a dot-com-era start-up that was later taken public. Coming from a family of entrepreneurs, I understand the real-world pressures, risks, and rewards of growing a business from the ground up.

I helped build Deloitte’s US Private Company business from $300 million to $4.5 billion, launched Converge, Deloitte’s cross-industry AI and hybrid-software venture, and created the Mid-Market Technology Survey to track innovation and investment trends in private, PE-backed, and family-owned firms. Creator of The SHIFT Method™ an AI disruption diagnostic for mid-market and minority-owned businesses. These experiences allow me to bring both strategic foresight and hands-on practicality to every client conversation.

Today I focus on helping growth-oriented companies in the 10–250 employee range gain clarity, accountability, and traction through the proven EOS® framework. For some, that means scaling confidently; for others, preparing for new capital, acquisition, or succession. My goal is simple, I want to help leaders build healthier teams, stronger companies, and lasting impact for their families, investors, and communities.

I work with growth-minded companies in construction, technology, clean energy, healthcare, manufacturing, automotive, and professional services across St. Louis, Chicago, and Northern California while collaborating nationally with select clients through strategic partnerships and referrals. With decades of strategy, technology, and leadership experience, I help business owners simplify complexity, strengthen execution, and scale with confidence using EOS®.