Matthew Bailey
EOS Implementer for entrepreneurs and leadership teams in California
| Hourly rate range | $125 to $300 an hour |
|---|---|
| Focus areas | Scaling and growthOperations and systemsLeadership and team buildingStartups and foundersReal estateTeam performanceLeadership developmentAssessments (360, DISC, CliftonStrengths) |
| Works with | Founders and business owners and Executives |
| Also coaches | Executive coach |
| Based in | Sunnyvale, California, United States |
| Credentials | Professional EOS Implementer |
Matthew Bailey is a Professional EOS Implementer who helps entrepreneurs and their leadership teams fix root problems, align around a shared vision, and build systems that hold people accountable. He began his career in engineering at NASA Ames Research Center. He then built a real estate investment company from scratch with no outside capital. It grew to more than 1,000 transactions. He has worked as both the Visionary and the Integrator.
What Matthew helps with
Matthew works with business owners and leadership teams who want clearer roles, better accountability, and operations that run without constant owner input.
- Finding the root causes behind business problems
- Aligning leadership teams around a shared vision
- Building accountability into daily operations
- Getting the right people in the right seats
- Capturing tribal knowledge in written systems
- Learning to delegate and step back from daily work
- Scaling a business without burning out the team
Who Matthew works with
Matthew works with entrepreneurs and their leadership teams. He understands both the Visionary and the Integrator roles, since he has held each one. His clients are leaders who want more structure, clearer accountability, and a team that works well together as the business grows.
How Matthew works
Matthew uses the EOS framework to bring clarity, accountability, and alignment to leadership teams. His approach rests on three traits. He is diagnostic, looking for hidden root causes instead of surface symptoms. He is adaptive, helping leaders spot mindset challenges that data alone cannot solve. He is systems-minded, building systems that capture tribal knowledge and help leaders delegate. He also draws on DISC, PI, Working Genius, and LCP360.
Background and qualifications
Matthew started his career in engineering at NASA Ames Research Center, where he worked on systems analysis and operational optimization. He is a former Army aerospace engineer and experimental helicopter researcher. Alongside that work, he built a real estate investment company with no prior experience or outside capital. It became one of the largest vacant land investment companies in the U.S. and completed more than 1,000 transactions. He used EOS to lead that business and has worked in both the Visionary and Integrator seats.
Matthew Bailey pricing
Matthew Bailey reviews
The CoachVouch take
A former NASA Ames engineer who built a large vacant land investment company and ran it as both Visionary and Integrator.
Best for entrepreneurs who want to fix root issues, build accountability, and get their leadership team aligned.
Common questions
How much does Matthew Bailey charge?
Coaching with Matthew runs $125 to $300 an hour. Request an intro for an exact quote.
What does Matthew Bailey help with?
Matthew Bailey helps with finding the root causes behind business problems, aligning leadership teams around a shared vision, building accountability into daily operations and getting the right people in the right seats.
Is Matthew Bailey certified?
Matthew Bailey lists: Professional EOS Implementer.
Has Matthew Bailey run his own business?
Yes. He built a real estate investment company from scratch with no outside capital. It grew to more than 1,000 transactions.
Which assessments does Matthew Bailey use?
He has deep experience with DISC, PI, Working Genius, and LCP360.
How do I contact Matthew Bailey?
Request an intro on this page. It's free, and we'll connect you with Matthew and, if you want, 2 or 3 similar coaches to compare.
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Last updated September 2026. Request a correction.