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This military spouse couldn't find anyone to hire her—so she created a company that would

Squared Away connects highly skilled military spouses with companies who need extra hands on deck.
Michelle Penczak, owner of Squared Away.
Michelle Penczak, owner of Squared Away.Elise Jillian Photography

Michelle Penczak, 32, had a job that she really enjoyed—working as a personal assistant for a lobbyist in Washington, D.C. But there was just one catch … she had fallen in love with a Marine.

“When you marry a Marine, you can’t take your job with you,” Penczak said, referring to the frequent moves that are often part of military family life.

When her husband, Maj. Sean Penczak, was stationed in Jacksonville, North Carolina, Penczak went on dozens of job interviews. “The interview would always go really well,” Penczak said, “and then they’d ask a personal question, which lead to the fact that my husband was in the military, and the tone would change to: ‘Thanks for coming out to see us.’” Penczak said she was determined to start working but “no one would hire me because I was a military spouse.”

Penczak shifted her focus to remote work as a virtual assistant for a company called Zirtual. But when Zirtual went bankrupt in 2015, Penczak was once again jobless.

“My husband was deployed, I was three months pregnant with our first baby, and I had no idea what to do,” Penczak said.

Becoming her own boss

Penczak had become so valuable to her Zirtual clients that sevreal stayed with her after the company folded. The business continued to grow organically, and Penczak eventually started her own team by hiring her first assistant, Kelsey Opel, who is now her director of operations.

Opel, another military spouse, had gone on 25 interviews before Penczak hired her. “I couldn’t get a job, and I had hit the point of not wanting to just be a stay-at-home mom,” Opel said. “Once I started working, I felt valued again. I was getting professional fulfillment, getting amazing contacts and supporting my family at the same time.”

Major Sean Penczak, Michelle Penczak and their two sons, Sawyer, 3, and Jamison, 4 months.
Major Sean Penczak, Michelle Penczak and their two sons, Sawyer, 3, and Jamison, 4 months. Courtesy of Michelle Penczak

Penczak officially launched her company, Squared Away, two years ago—on Veterans Day in 2017. The business connects highly skilled military spouses with companies who need extra hands on deck. Penczak noted her 70 team members aren’t just virtual assistants. “They’re chief executive assistants—our clients’ right hand. They’re project managers, they’re the social media team, they’re human resources…” said Penczak.

They can even meal plan or hire a plumber if you need one. Most clients begin with Squared Away’s $500/month plan for 15 hours of help, and then increase from there.

Supply and demand

Though Penczak began her company with clients she already had on board, it wasn’t always smooth sailing. She had to get the word out to increase her client roster while making sure she had qualified assistants to meet the demand—and those assistants had to be readily available in the time zone of each client’s choice. And since 95 percent of her new business is client referrals, she wanted to hire top-notch people to keep those referrals rolling in.

She partnered with Hiring Our Heroes, an initiative that connects veterans, service members and military spouses with meaningful employment. Hiring Our Heroes vets interested candidates, who must then pass a series of tests and interviews before being accepted into Squared Away’s training process. Not everyone makes it through training, Penczak cautions. Those who do are eligible to work with clients.

Penczak’s effort to engage and employ military spouses led to her being named Military Spouse of the Year for Kaneohe Bay.

Daily operations

Coordinating 70 people in multiple time zones and various countries is an enormous undertaking. “There’s a lot of caffeine involved,” joked Penczak. Mom to 3-year-old Sawyer and 4-month old Jamison, Penczak, who is currently living on Oahu in Hawaii, wakes up at 3 a.m. Hawaiian time in order to greet her team on the east coast. And for half of 2019, she was solo parenting while her husband was deployed in Australia.

“Motherhood is something we celebrate within Squared Away,” Penczak said. Her company was still in its infancy when her first child was born, and “it became a running joke that I was in labor with Sawyer and putting up my out-of-office message while getting my epidural.”

But she and her team have now set up an internal support system at Squared Away that helps moms get ready for their new additions. “I did take one client call three days after Jamison was born,” Penczak said, “but then I gave myself a month to get into a good mom routine while my team stepped up to help.”

Penczak also gave her top tips for women who are thinking about starting their own company:

"Always be empathetic—both internally and externally.”

Listening and understanding her team’s needs has led to an enthusiastic and dedicated staff. Doing the same for her clients resulted in an extremely high satisfaction and referral rate.

“There isn't a roadmap for how to navigate bumps in the road—go with your gut and surround yourself with people who support you.”

Penczak teamed up with Shane Mac, the CEO of an automated assistant platform Assist, to co-found Squared Away for exactly this reason. While Penczak worked to essentially clone herself and train other military spouses to be top-notch virtual assistants, Mac leant his expertise in growing and scaling a business.

Make time for you every day.

Just “15 or 20 minutes here or there does incredible things for your sanity!” said Penczak. One of the reasons Penczak rises so early every day is to sneak in quiet coffee time “before mom mode kicks in.”