Taylor Lingerfelt is a proud active duty Army spouse, mom of two, and Team Lead at Squared Away. She began her journey with the company in 2021 while at home with her kids, seeking a way to reconnect with her own identity. Over the years, she’s held multiple internal roles, growing her skills in leadership, client success, and remote team management. Today, Taylor is passionate about finding balance between family life and career, leading with empathy, and embracing the beautiful chaos of military life. Her story is a testament to the resilience, adaptability, and leadership that military spouses bring to the workforce.

In this episode of Beyond Orders, Taylor shares how she built a fulfilling career from home, the challenges and rewards of managing a remote team, and the lessons she’s learned about leadership, delegation, and staying grounded while life moves at military speed.

This week on Beyond Orders, we sit down with Libby Jamison, a powerhouse attorney, policy strategist, and unapologetic advocate for military families. With nearly 20 years in law, government, and grassroots organizing, Libby has worked everywhere from the Department of Veterans Affairs to the West Wing, where she served as Senior Advisor to Joining Forces, Dr. Jill Biden’s initiative supporting military families, caregivers, and survivors.

As former President of the Military Spouse JD Network, Libby helped drive licensing reforms across more than 40 jurisdictions, opening professional doors for spouses nationwide. She has earned national recognition, including Military.com's Spouse Changemaker of the Year and a spot on the 2023 Mighty 25, and for good reason.

In this episode, Libby shares the behind-the-scenes truth about policymaking, the personal toll and triumph of advocacy, and why military spouses are more than just resilient. We are revolutionary!

Meagan Eskew started as a virtual assistant with Squared Away in 2020 and worked her way up to become our Director of Client Connections. A single mom who battled, and beat, breast cancer, Meagan didn’t just climb the ladder, she built her own. Now, she’s stepping into a full-time role with a client buyout, proving what happens when grit meets opportunity.

She homeschools her kids, leads with heart, and shows exactly what betting on yourself looks like when life throws everything at you.

If you’ve ever wondered whether it’s possible to go from surviving to thriving, this episode is your answer.

🎧 Listen in and see why Meagan is one of the toughest, smartest women we know.

What does it take to grow from a virtual assistant to a trusted executive leader, all while proving that military spouses are some of the strongest leaders in the workforce?

In this episode of Beyond Orders, Michelle Penczak, CEO of Squared Away, interviews Jessica Ryan, the company’s Chief People Officer. Jessica started in 2020 as a virtual assistant and steadily rose through the ranks, from Team Lead to the executive team, by leading with empathy, consistency, and quiet strength.

Jessica shares how she built trust, supported hundreds of military spouse virtual assistants, and helped shape Squared Away’s culture. Her story is proof that military spouses are not just support staff, they are leaders, innovators, and change-makers.

If you’re a military spouse ready to grow your career, step into leadership, or prove that you’re more than “just an assistant,” this episode is a must-listen.

What you’ll learn in this episode:

How to grow from support roles to leadership positions

Why military spouses make exceptional leaders

The power of empathy and consistency in building influence

How to lead without a loud voice and still be heard

Listen now to discover how you can own your story, your skills, and your seat at the table.

In this episode of Beyond Orders, host Michelle Penczak, CEO of Squared Away and military spouse, sits down with Sara Brooks-Glover, Chief Operations Officer at Squared Away, to talk about career growth, remote leadership, and scaling systems in a mission-driven company.

Sara shares her inspiring journey from starting as a virtual assistant to rising through the ranks as Director of Finance and Compliance, leading Talent and Development, and now serving as COO. She offers insights into how she built scalable operations, aligned cross-functional teams, and leaned into reinvention every step of the way.

Whether you're managing a remote team, hiring virtual assistants, building business infrastructure, or navigating a leadership transition, this episode is packed with practical advice and lessons in resilient, empathetic leadership.

Keywords: military spouse career, remote team management, virtual assistant business, leadership development, female COO, career growth, business operations, hiring systems, delegation strategies, Squared Away, Michelle Penczak, Sara Brooks-Glover, Beyond Orders Podcast

🎧 Subscribe for more interviews with military spouses, remote leaders, and professionals redefining what’s possible.

In this deeply moving episode of Beyond Orders, host Michelle Penczak sits down with Tiffany McCawley, a military spouse and mother of five whose faith and resilience leave a lasting impression. Tiffany became part of the Squared Away team in 2020, but her journey began long before that.

In 2015, Tiffany endured every parent’s worst nightmare; the loss of two of her children in a tragic accident. What followed was not a neatly wrapped healing journey but a raw, honest walk through grief, anchored by her faith and a quiet strength developed through lived experience.

Tiffany shares how she moved from surviving to thriving, how her work brought renewed meaning, and how her belief in God gave her the courage to keep going when nothing made sense. She speaks candidly about the causes close to her heart, including Let Them Live, supporting foster and at-risk youth; While We’re Waiting, empowering women facing unexpected pregnancy; Backpack Friends, feeding food-insecure children; and Ride Safe Foundation, striving to reduce underage drinking and increase safe rides for teens.

To learn more about Tiffany’s journey, visit her blog: theclanmccawley.blogspot.com.

Some causes that are important to the McCawley Family:

- https://ridesafefoundation.org/

- https://www.backpackfriends.org/

- https://whilewerewaiting.org/donate/

In this episode of Beyond Orders, host Michelle Penczak speaks with Rachel Hornbeck, the Director of Talent and Development at Squared Away, about her journey from being a stay-at-home mom to a leadership role within the company. They discuss the supportive culture at Squared Away, the challenges of imposter syndrome, the importance of community, and the personal stories of adoption that have shaped their lives. Rachel shares her insights on leadership, accountability, and the hiring process, culminating in a reflection on the theme of reinvention and personal growth.

In the inaugural episode of Beyond Orders, host Michelle Penczak sits down with Jordan Streetman Cole, Chief Experience Officer at Squared Away, for a powerful conversation about the realities of military spouse life and the unexpected opportunities that can come from uncertainty.

Together, they unpack Jordan’s journey from applying to Squared Away out of sheer desperation to growing into a key leadership role within the company. Along the way, they explore themes of reinvention, resilience, and the deep need for stability in a life shaped by constant change.

This episode dives into the unique strengths military spouses bring to the workforce, the transformative power of meaningful assistant-client partnerships, and why building community and trust is at the heart of it all. Whether you’re navigating career transitions, PCS chaos, or simply looking for a story that reminds you you’re not alone, this one’s for you.

Because while military orders may move us, they don’t have to define us.

Jordan's book reference - Time, Talent, Energy