Chris Jackson

Supply chains, pricing models, workforce structures, competitive moats; AI is stressing all of it simultaneously. Most mid-market founders are navigating this with the same intuitive style and leadership approach that built their companies. That works until growth, disruption, and change arrive faster than instinct can handle. What you need then isn’t more hustle. It’s structure, clarity, and a foundation built for what’s actually coming.

I’m a seasoned entrepreneur, Air Force veteran, and retired Deloitte Consulting Managing Director with 30+ years of leadership, strategy, and emerging-technology experience. Over 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. I come from a family of entrepreneurs. I understand the real-world weight of building something from the ground up, and I bring that perspective into every client engagement.

At Deloitte I helped scale the US Private Company business from $300 million to $4.5 billion, one of the most sustained mid-market growth stories in the firm’s history. As the Firms first Chief Commercial Officer, I helped launched Converge by Deloitte, a cross-industry AI and software venture, and created the Mid-Market Technology Survey designed to track technology innovation, use and investment trends across private, PE-backed, and family-owned businesses. That work, combined with two decades of facilitating C-suite strategy sessions, leadership offsites, and organizational alignment work for some of the most complex companies in the world is the experience base I bring to every EOS engagement.

It’s also what led me to develop The SHIFT Method™, a proprietary AI disruption diagnostic for mid-market and minority-owned businesses. Where most frameworks tell you AI is coming, SHIFT maps exactly where it’s restructuring your competitive position, compressing your margins, and creating new opportunity. This allows leadership teams make deliberate decisions instead of reactive ones. It’s a standalone executive engagement, and the strategic clarity it produces is what makes the EOS work that follows land faster and go deeper. www.theSHIFTMethod.ai

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 it means preparing for new capital, acquisition, or succession. My goal is straightforward, to make a difference by helping leaders build healthier teams, stronger companies, and lasting impact for their families, investors, and our communities.

I work with companies in construction, technology, clean energy, healthcare, manufacturing, automotive, and professional services across St. Louis, Chicago, Northern California and nationally with select clients. Whether you’re a founder who’s outgrown your instincts, a PE-backed operator navigating a complex portfolio, or a diverse business leader building something that lasts, if you’re ready to get a grip on your business, let’s talk.