Colonel Ossen D’Haiti

Background

• Service Record: Nearly 27 years in the Marine Corps as a Harrier pilot and cyber warfare leader.
  
• Last Assignment: Commander, Marine Corps Cyberspace Warfare Group at U.S. Cyber Command.
  
• Education & Training: Degrees from the Merchant Marine Academy and Naval War College; fellowships and executive programs at MIT, Harvard, Wharton, Columbia, and SANS. 

Transition Journey Overview

Oz focused on his intentional and strategic transition to the private sector, using a combination of:

• Long-term career planning via personal tools (e.g., a career tracker spreadsheet),
  
• Mentorship and sponsorship,
  
• Networking and informational interviews. 

He emphasized the importance of early preparation and viewing transition as a multi-year process.

Key Lessons and Frameworks

1. “You Are in Charge of Your Own Career”

• Oz stressed ownership of professional development, leveraging every assignment as a stepping stone.
  
• Built a visual time chart throughout his Marine Corps career to track progress and target future roles. 

2. Mentors, Advisors, and Sponsors

• Advisors help solve problems.
  
• Mentors offer career guidance from personal experience.
  
• Sponsors advocate for you when you’re not in the room.
  
• All three roles are vital; sometimes one person plays multiple roles. 

3. Four Essential Questions for Transition

From years of networking, Oz distilled transition prep into these guiding questions:

1. Where do you want to live?
   
2. What do you want to do?
   
3. How much money do you want to make?
   
4. Who do you want to work for? 

These questions clarify priorities and help navigate the complexity of post-military options.

4. Strategic Decision-Making

• Family and personal life heavily influenced decisions.
  
• Accepted an unaccompanied tour and declined early retirement to align professional opportunities with family needs. 

Entering the Private Sector

• Oz joined Hewlett Packard Enterprise after being personally recruited by a VP who recognized his leadership potential.
  
• He valued a strong mentorship commitment from his new employer and sought opportunities for growth, not just placement. 

Initial Challenges:

• Adjusting to remote work culture.
  
• Understanding matrix organizations with fewer direct reports than in military units.
  
• Translating military leadership to corporate language. 

Long-Term Success:

• Promoted three times in six years.
  
• Leads strategic IT solutions for the Intelligence Community in Northern Virginia. 

Advice for Those Transitioning

• Start early: Plan 3–4 years out.
  
• Talk to many people: Treat each conversation as valuable data.
  
• Tailor your resume: Avoid mass submissions; hand it to trusted contacts.
  
• Think beyond MOS: Leverage broader leadership and problem-solving skills.
  
• Understand civilian lingo and metrics: Translate military experience into business terms. 

“Footprints and Fingerprints”

• Your past experiences and influence leave marks that shape both your reputation and trajectory.
  
• Be intentional with every step and maintain high performance and relationships.They may open unexpected doors. 

Audience Engagement & Reflections

• Participants included transitioning officers and veterans seeking insights.
  
• Several questions explored:
  • Timing of entry into cyber.
    
  • Role of peers and subordinates in mentorship.
    
  • How unexpected opportunities and visibility shape career direction. 

Closing Notes

• Colonel de Haiti’s story is a case study in disciplined preparation, leveraging networks, and aligning purpose with opportunity.
  
• The session concluded with a recognition that transition is ongoing, not a one-time event, but a continuous process of growth.