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Professional

Matthew Bailey

  • Sunnyvale, California, United States

  • San Francisco, California, United States

  • San Jose, California, United States

Offers Virtual Sessions

I help ambitious entrepreneurs solve root issues, align teams, and build accountable systems that drive lasting results.

Meet Matthew Bailey

  • Built and scaled one of the largest vacant land investment companies in the U.S.
  • Former Army aerospace engineer turned entrepreneur
  • Personally operated from both the Visionary & Integrator seats
  • Deep experience with DISC, PI, Working Genius, and LCP360
  • Former Eagle Scout, collegiate track captain, and experimental helicopter researcher
  • E: matthew.bailey@eosworldwide.com | P: (201) 887-0637

Book Your Free Introductory Call

Ready to get more of what you want from your business? Let’s talk. Book your free introductory call with me to share your business needs and challenges. I’ll share my background and style. No pressure, just a real conversation to see if we’re the right fit.

My Approach / 3 Uniques

Diagnostic
Aerospace engineering trained me to identify hidden root causes, not just surface symptoms, creating lasting operational change.
Adaptive
I help leaders recognize adaptive and mindset challenges that data alone can’t solve, unlocking healthier growth and leadership.
Systems-Minded
I build systems that capture tribal knowledge, strengthen accountability, and help leaders delegate, elevate, and scale sustainably.

What It’s Like to Implement EOS

Hear from the business leaders and teams I’ve had the privilege of guiding through their EOS journey.

Expertise & Insights

Insightful guidance, practical tips, and real-world stories to help you strengthen your leadership team and run a better business.

From Lion to Lamb & Back Again

In most of North America, the saying goes that March comes in like a lion and out like a lamb. For many entrepreneurs, this phrase holds a parallel to their business experience....
Read More
  • Understand the six keys to building a truly great organization
  • Roll up your sleeves and confront your organizational issues head-on
  • Learn how to get everyone focused on achieving a clear company vision
  • Begin to instill discipline and accountability throughout your organization

My Upcoming Events

There are no current upcoming events. Please check back regularly and follow us on social for the latest news and events!

Professional Implementer

matthew.bailey@eosworldwide.com

Phone: 201-887-0637

  • Sunnyvale, California, United States

  • San Francisco, California, United States

  • San Jose, California, United States

About

My career began in engineering, working at NASA Ames Research Center where I focused on systems analysis, operational optimization, and identifying small problems before they became bigger ones. That experience shaped how I think about organizations today: most challenges are symptoms of deeper issues.

Alongside that work, I built a real estate investment company from the ground up with no prior experience or outside capital. Over time, it grew into a multi-person organization completing more than 1,000 transactions, requiring strong leadership, clear processes, and scalable systems to sustain growth.

EOS became the framework that transformed both my business and leadership. Through EOS, I experienced firsthand what happens when leadership teams gain clarity, accountability, and alignment around a shared vision. Having operated in both the Visionary and Integrator seats, I understand the strengths and pressures that come with each role.

Today, I’m passionate about helping entrepreneurs build businesses that run better and leadership teams that work healthier together. My approach is practical, engaged, and focused on solving root issues, simplifying operations, and creating organizations built for long-term success.

 

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