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prepare. lead. perform.

ABOUT OSPREY ARROW

Osprey Arrow helps organizations perform under pressure and avoid being caught off guard. Risk assessments find the exposure, organizational design and leadership training fix the structure and people behind it, while mentoring and keynotes carry the message. 

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We bring special operations discipline to risk, leadership, and organizational design, so your team can perform when conditions are worst.  Most of what makes an organization resilient isn't security hardware. It's people, processes, and leadership. We assess and improve all three where you get a risk list, a leadership plan, and a path to implement it.  Your team stays in charge; we make it stronger.

 

Built on decades in special operations: finding what others miss and building teams that hold up under pressure.

our mission

Osprey Arrow’s mission is to develop capable, confident leaders and resilient organizations through practical coaching, mentoring, training, and strategic advisory services – equipping people to make sound decisions, navigate uncertainty, and perform in an increasingly complex and uncertain world.

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Jim O'Brien

​Osprey Arrow founder Jim O'Brien, a retired U.S. Army Special Forces Colonel, served 29 years as a Green Beret and has extensive experience in special operations, intelligence, and counterterrorism. He deployed on numerous sensitive international operations throughout his career, culminating in his service as the USSOCOM’s Deputy of Operations, responsible for the Enterprise’s global operations and as the Chief of International Operations, leading our International Partners in combined endeavors. A graduate of USMA, Naval Post Graduate School, U.S. Army War College, and Harvard Business School Executive Program.

29

Years of Army Service

25

Years as a Green Beret

5

Publications & Podcasts

13

Keynote Addresses

our approach

We help organizations prepare, lead, and perform through three areas of focus:

Leadership Development

Develop capable, confident leaders prepared to make sound decisions.

Organizational Resilience

​Build organizations equipped to adapt, manage risk, and perform under pressure.

Strategic Advisory

Bring experienced perspective to complex organizational and strategic challenges.

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Preparation
changes performance

Risk is inevitable. Uncertainty is unavoidable. Being unprepared doesn't have to be.

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We help organizations identify the challenges ahead, develop capable leaders, build resilient teams, and prepare to perform when circumstances demand it.

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We don't just identify the risk. We help you prepare for it - and respond when preparation isn't enough.

Alex Washington, FL

“Jim delivered an outstanding keynote that was both engaging and thought-provoking. He brought leadership concepts to life through practical insights and real-world experience. Our audience walked away with ideas they could immediately apply, and his message continued to generate conversation long after the event.”

Build Your Readiness

You don't get to choose when uncertainty arrives. You can choose how prepared your people are when it does. ​Let's build that capability before you need it.

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