Meet Your Counselor - Cheyenne Derrick
Cheyenne Derrick - Veteran Career & Transition Counselor | US Navy, Retired
1. Tell us a little about yourself and your background.
I am a dynamic and results-driven HR professional with a deep passion for empowering veterans through career counseling and transition support. With a strong foundation in Human Resource Management, training development, and data analytics, I bring over 15 years of experience across military, corporate, and nonprofit sectors. I thrive in environments where I can use strategic thinking and relationship-building skills to drive meaningful change for individuals and organizations. I am also currently advancing my skills by pursuing a Bachelor of Science in Data Analytics to further integrate data-driven insights into my work.
2. What is your military background? And did you attend any additional college or educational courses?
I proudly served in the United States Navy for 22 years, where I held roles as a Career Counselor, Human Resource Manager, Benefits Specialist, and Instructor/Master Training Specialist. Throughout my career, I advised and counseled over 40,000 service members globally, managed HR operations, and led large-scale training initiatives.
Academically, I hold a Bachelor of Science in Business Administration and a Master of Science in Human Resource Management. I am currently enrolled in a Bachelor of Science program in Data Analytics to deepen my technical expertise. I also hold certifications, including Certified Post-Secondary Instructor and several Department of Labor certifications in counseling and office management.
3. What inspired you to join Still Serving Veterans?
My passion has always been to continue serving those who have served. Still Serving Veterans' mission to empower veterans in their post-military journeys resonated deeply with me. After my own transition from military to civilian life, I understood firsthand the challenges and uncertainties veterans face. Joining SSV was a natural extension of my desire to use my experience, empathy, and skills to guide and uplift fellow veterans as they navigate their next chapter.
4. What does a typical day look like for you at SSV?
A typical day for me at SSV involves working closely with veterans to develop personalized career transition plans. I assess their skills, translate their military experience into civilian career language, assist with resume development, and coach them on interview techniques. I also maintain strong relationships with employers and community partners to expand employment opportunities. Facilitating workshops, collaborating with mental health professionals for holistic support, and applying data analytics to improve our services are also essential parts of my daily role.
5. What do you find most rewarding about your work here?
The most rewarding part of my work is witnessing a veteran’s transformation from uncertainty to confidence. Seeing a veteran secure a meaningful civilian role, knowing that I helped them recognize their worth and navigate their journey, is incredibly fulfilling. Every success story reaffirms why I chose this career path — it’s about changing lives and honoring their service.
6. In your experience, what’s the biggest challenge veterans face when transitioning to civilian life?
One of the biggest challenges veterans face is translating their military experience into civilian terms that employers understand and value. Many veterans struggle with recognizing the depth and relevance of their skills outside of a military environment. There’s often also a sense of loss of community and identity after leaving service, which can make the transition feel overwhelming without the right support system.
7. What advice would you give a veteran who’s hesitant to seek support?
I would remind them that seeking support is not a sign of weakness but a strategic move toward success. Transitioning is a major life change, and having a team behind you makes the journey smoother and more empowering. Organizations like SSV exist specifically to help veterans succeed — and everyone here understands the unique challenges veterans face. You don’t have to navigate this journey alone.
8. What are your hobbies or interests outside of work?
Outside of work, I have a deep passion for coaching and mentoring. I’ve spent the past six years coaching softball, fostering teamwork, discipline, and leadership among young athletes. I also enjoy public speaking, curriculum development, and expanding my data analytics expertise through ongoing studies and projects.
9. Finally, what does “Still Serving Veterans” mean to you?
"Still Serving Veterans" means continuing a lifelong commitment to service — a promise that doesn’t end when the uniform comes off. It symbolizes honoring the sacrifices of our nation’s heroes by ensuring they have the tools, resources, and opportunities to thrive in civilian life. It’s about standing shoulder-to-shoulder with veterans, advocating for them, and helping them discover their next purpose.
