About

I help leaders build the organizational operating systems — the strategy, structure, processes, and culture — that allow companies to scale without breaking, especially as AI accelerates everything around them.

I write about this because I believe the organizations that will thrive in the AI era aren't the ones moving fastest. They're the ones with the deepest stability — the ones that have built enough weight beneath the surface to carry more sail without capsizing.

Connect with me on LinkedIn.

My Background

I spent over two decades building, scaling, and maturing organizations at the intersection of technology, strategy, and federal government services.

Most of that time was at Halfaker and Associates, where I served in several executive roles including COO, CTO, and CIO/CISO, helping the company grow from a small government services firm to over 550 employees. That work meant building the organizational infrastructure from startup to midsize operations: the operating cadences, the roles and responsibilities frameworks, the knowledge management systems, the compliance programs, the accountability rhythms, and the cultural principles that allowed hundreds of people to move effectively in the same direction.

That experience, building the systems that let a company scale, is the foundation of what I write, teach, and advise on today. The company's eventual acquisition by SAIC validated what I'd come to believe: organizations that invest in operational stability don't just survive growth. They become valuable because of how they're built, not just what they deliver.

I hold degrees in Computer Engineering from the University of Virginia and Information Systems from Johns Hopkins University.

What I Do Now

Today I work as an advisor and investor, helping leaders navigate the same challenges I spent years solving firsthand.

Advising. I work with growing organizations, for-profit and nonprofit, on the hard, unglamorous work of building enterprise operating systems: clarifying roles and decision authority, designing operating cadences, building knowledge management infrastructure, connecting strategy to execution, and preparing organizational foundations for AI adoption. I also teach at the Veteran Institute for Procurement (VIP), where I help veteran-owned businesses build the operational maturity needed to compete for larger government contracts.

Investing. I angel invest and venture invest through groups like New Dominion Angels, District Angels, and dcode capital. What I've learned is that the companies I most want to invest in are the ones that are pursuing noble goals like serving Americans better and remind me of building Halfaker, where we had a team that valued building a resilient organization.

Writing. This website, mikehking.com or The Keel, is where I work out ideas, share frameworks, and build on what I learned scaling an organization through some of the most demanding compliance and operational environments in the federal sector. I write for leaders who feel the pressure to move fast, especially with AI, but know their foundation isn't ready to carry the load. If that sounds like you, subscribe and I'll share what I've learned.

Why "The Keel"?

The name comes from sailing, which I learned teaching it as a camp counselor at Camp Piankatank during two summers in college. I split those years between systems research in computer processor branch prediction and teaching kids to sail the Chesapeake Bay, a combination that probably explains more about how I think than anything else on this page.

On the water, you learn quickly that the keel is the most important part of the boat. It's the weighted fin beneath the surface that prevents capsizing. But more than that, it's what translates wind into direction. Without a keel, you drift wherever the wind blows. With one, you can navigate a precise course — and the stronger the wind, the more the keel matters.

That's the core insight behind everything I write: the faster the world moves, the more your organization depends on the weight beneath the surface. The documented processes. The clear roles. The operating cadences. The institutional knowledge that doesn't live in one person's head. That weight is your keel. And in the AI era, the wind has never blown harder.

I created The Keel to help leaders build that stability into their organizations — so they can carry more sail without tipping over.

Personal

When I'm not whiteboarding strategy or advising founders, I'm usually on an adventure with my family — skiing, boating, 3D printing, cycling, or finding excuses to drive our Honda S2000 convertible on errands that are more fun with a stick-shift sports car.

What This Site Covers

If you're a leader scaling an organization and thinking about any of the following, you're in the right place:

How to build an enterprise operating system that doesn't depend on tribal knowledge. How to connect your strategy to daily execution with real traceability. How to design accountability systems that make ownership the path of least resistance. How to build organizational maturity under demanding compliance frameworks. How to prepare your foundation for AI before you deploy AI. And how to do all of this without losing the entrepreneurial energy that got you here.

Explore the Keel Framework for the conceptual architecture, or dive into recent posts to see these ideas applied to real organizational challenges.