Beyond Orders

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.
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.

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
The podcast aims to empower military spouses to rewrite the rules of their careers.
Desperation often drives military spouses to seek new opportunities.
Stability in employment is crucial for military spouses facing frequent relocations.
Resiliency is a key trait of the Squared Away team.
Building a community among military spouses enhances support and connection.
Successful client-assistant matches require time and investment in understanding each other.
Celebrating wins, both big and small, is essential for motivation.
Reframing opportunities for military spouses can change perceptions in the workforce.
Reinvention is about honoring one's potential and evolving into the best version of oneself.
Leadership is about empowering others and leading by example.