Skyler founded Bailey Military Support in honor of her beloved mentor, Command Sergeant Major Scott Bailey, to continue his legacy of caring for service members and their families. Sky is a proud wife and mother of two boys. She met her husband while they were both serving on active duty in Alaska, and they've been married since 2010. She strives to glorify God in her personal, academic, and professional life.

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She may hold several titles, but if you ask her, she’s simply Sky, just a person trying to answer a calling. She loves planning themed support group meetings and events, making things fun for our military children, and of course, making sure everyone gets a good meal! One of her favorite parts of Bailey Military Support is getting to know our members and their families. She makes it a point to learn everyone's name, even if she has to write a few down at first.

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Sky loves giving back to service members, veterans, and their families, especially those who may not have family nearby. When Sky was looking for a community where her family could connect with other military families, she wanted a place where veterans’ children were included and families with special needs felt welcomed and accepted, never like a burden. When Sky couldn’t find the kind of community she was looking for, she decided to create one. That vision became Bailey Military Support.

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Sky's military service and volunteer work have earned her several honors, including El Paso County's 2021 Veteran of the Year, the 2023 American Red Cross Community Hero Award, the 2024 Ent Community Advocate Award for Southern Colorado, and a 2026 Congressional Commendation from Congressman Jeff Crank.

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However, of all the titles she holds, her favorite will always be Mom.

 

As Scott Bailey’s sister, Vicki has a deeply personal connection to Bailey Military Support and the mission behind everything we do. As our Vice President, she plays an important role in every major decision our organization makes. From helping manage operations and finances to guiding the direction of Bailey Military Support, her insight and dedication are invaluable to our mission. Our President turns to Vicki so often for her thoughts and guidance that she should probably have her own work number by now! 🤣 She also helps keep our organization grounded in our Christian values and the faith that guides our work.

Although she lives out of state, Vicki contributes in every way possible from afar! She is constantly giving from her own pocket to help support our members and their families. We lovingly call her our Amazon Wish List Fairy because she is always making sure items from our wish lists are purchased for our kiddos, especially during Easter and Christmas!Vicki also travels from Arizona whenever she’s able to attend our annual suicide prevention event, A Night of Hope.

Vicki and her husband, Rick, have been married for 49 years and are proud parents of three children and grandparents to three grandchildren. They continue to show us, through their example, what a lifetime of love and commitment looks like!

Vicki is so much more than simply a board member. She holds a special place in the heart of Bailey Military Support, and we couldn’t imagine our organization without her. We are so thankful for the love and dedication she pours into keeping Scott’s legacy alive. 

Sabrina serves as our Treasurer and is an important part of Bailey Military Support’s Executive Board. Although she now lives out of state, she helps oversee our finances and budgets and works with our board to make decisions about how we can best support our military community.

 

Sabrina originally joined us as our Children’s Director and later served as our Vice President, wearing countless hats along the way. From budgets, rosters, and strategic planning to making cotton candy for our military kiddos, there isn’t a job she hasn’t done!

 

She was also our very own Pinterest mom. Sabrina spent hours personalizing Valentine’s boxes with her Cricut, five hours making a Grinch balloon arch, and even an entire week setting up a carnival-themed support group meeting.

 

When a soldier tragically lost his wife and suddenly became a single dad to a newborn, Sabrina played a big role in our Christmas Blessing Program, helping us collect over $1,000 worth of necessities for him and his baby during their first Christmas together.

 

We certainly miss having Sabrina at our meetings and events, but we’re so thankful she continues to serve on our Board of Directors, even from miles away.