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Squared Away— Tapping into the Military Spouse Workforce and Making Millions

Read time: 5 minutes

Good morning! It's Friday, February 16th. Today, we’re looking at Squared Away, a company hiring military spouses for virtual assistant positions that just crossed the $20M revenue mark!


Squared Away— Tapping into the Military Spouse Workforce and Making Millions

Serving in our nation’s military is honorable and a massive sacrifice, especially considering the extensive time away from family and notoriously low wages

To make financial matters worse, it is extremely difficult for military spouses to secure jobs— a subgroup with a 21% unemployment rate. 

Squared Away is addressing this problem, supplying jobs to military family members and growing revenue by 1,908% over the past three years!

So, What's the Business?

The inspiration for Squared Away came in 2015, when its founder, Michelle Penczak, lost her job as a remote assistant for Zirtual. 

This was a massive blow to Penczak. Having a virtual job was a necessity since most in-person employers shy away from hiring military spouses known to move between military bases every few years. To top it off, she was three months pregnant and desperately needed the income. 

Despite Zirtual going under, Penczak stayed afloat by taking five clients off the platform. Over the next few months, she started an LLC and worked up to 13 clients. 

Squared Away was born in 2017 when one of Penczak’s clients was scaling their business and wanted her to scale her virtual assistant operations with them. At first, she thought it would be impossible to manage as a new mom working from a military base in Hawaii. Then, she had her lightbulb moment. 

If she needed to find the right employees, why not reach out to the ~700,000 American military spouses who shared her struggles and were hungry to work?

Penczak posted virtual assistant positions on Facebook groups for military spouses and saw a massive response. However, she intentionally grew the company slowly, only adding one to two employees a month. 

Squared Away was profitable from day one, and by 2019, the company reported $983K in annual recurring revenue with 80 assistants and 100 clients. By 2020, revenue tripled to $3.1M

The company is still experiencing exponential growth, with $11M in revenue for 2022. Squared Away was featured on 2023’s Inc. 5000 list with 1,908% growth and $20M in revenue. What’s crazier is that Penczak pulled all this off with zero outside funding. 

Key Observation: Building a Company on Real Needs

Catering to an unserved labor pool can come with massive benefits. 

Of course, a societal benefit exists in helping people find gainful employment. But it can also benefit businesses as underserved labor pools entail a plethora of top candidates dying for work. 

Squared Away also uses its hiring of military spouses for branding and marketing purposes. Americans love supporting the military, and many of Penczak’s clients jumped at the opportunity to hire qualified virtual assistants from military families.

Penczak’s success with Squared Away is another example of the virtuous flywheel in action, showing the causal relationship between benefiting society and growing your company. 

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