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

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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.

• Real leadership starts when we stop waiting for permission to grow.
• The culture at Squared Away empowers individuals to thrive.
• Imposter syndrome is a common challenge for many leaders.
• Supportive communities can foster personal and professional growth.
• Heart and caring mentality are essential in leadership roles.
• Being open to feedback is crucial for success.
• Accountability is key to building trust within teams.
• The hiring process at Squared Away is thorough and thoughtful.
• Personal stories of adoption can create deep connections.
• Reinvention involves being brave enough to outgrow comfort zones.