Military Spouses Make Great Leaders & Jessica Ryan Proves It

July 21, 2025

Source: https://www.podbean.com/media/share/pb-vzydb-190ea8c


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.


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