Michelle Penczak
Michelle Penczak, founder and CEO of Squared Away.
- Michelle Penczak is the founder and CEO of Squared Away, which matches skilled virtual assistants with consultants, entrepreneurs, and executives at high-profile startups, entertainment studios, and venture capital funds.
- She launched her business, which has brought on more than 100 clients and doubled revenue year over year since it was founded, after her previous company - where she worked as a virtual assistant - went under.
- Her secrets to success include developing a rigorous process for vetting virtual assistants, keeping personal relationships with her employees, and encouraging collaboration among assistants, even remotely.
- She's proud to say that the "why" that keeps her going is providing a space for military spouses to pursue their passion without being limited by their location.
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A quick glance at her business metrics and you'd think Michelle Penczak was a natural entrepreneur.
Her company Squared Away, founded just over two years ago, matches skilled virtual assistants with consultants, entrepreneurs, and executives at high-profile startups, entertainment studios, and venture capital funds (and, full disclosure, my company Sweet Spot Content) to help with everything from scheduling to bookkeeping to crafting social media posts. Since the company was founded, she's brought on more than 100 clients, built a team of over 80 assistants, and doubled revenue year over year - all without a dime of outside funding. Penczak reported that in November of 2019, the company's annual recurring revenue was $983,856.
But before she founded Squared Away, she never envisioned herself running a company. "I always wanted to be doing something I loved, but I never saw myself as a CEO or entrepreneur," Penczak told Business Insider. "The prospect at the very beginning was a little bit terrifying."
It was a series of events that took her from that hesitancy to where she is now. First, she met, fell in love with, and married a US Marine - nearly guaranteeing that "home" would be a moving target for most of her life. She had a job she loved as a personal assistant, but she couldn't take it with her wherever she and her family went. Worse, she found that many employers were hesitant to hire her because of her inevitable need to move.
She eventually landed a job at virtual assistant company Zirtual, which felt like the perfect fit. The company's VAs were stationed all over the country, she had the chance to work with multiple clients at once, and she loved the camaraderie of being part of - and ultimately managing - a team. That is, until the company ceased operations in 2015. (It's since been acquired and resumed business.)
A few of Penczak's Zirtual clients stayed on with her, and soon she saw the capacity to grow her own business. So she hired a fellow military spouse, Kelsey Opel, to help build it out.
But it wasn't until a few months later that she saw just how big of an impact running a company could have. "[Opel] called me and said, 'I just want to tell you how grateful I am for you and for everything that you're doing for me and for our family.' She was three months postpartum, had been in the ICU with her little girl, and had interviewed at 25 different places and nobody wanted to hire her because she's a military spouse," Penczak recalled.
"When she told me that, it was like my heart jumped out of my chest. And I thought: This is why. My people are why. I wanted everybody else to be able to say, 'Squared Away took a chance on me, and it was the best move I ever made.'"
Since then, she's been tirelessly growing the business, exclusively hiring women and men whose spouses are in the armed forces.
Having worked at a growing startup myself, I know what a challenge scaling a company can be. So, what have been her secrets to finding success so quickly? I sat down (virtually, of course) with Penczak to learn more. Here are her tips on hiring the right people, staying connected to a growing (and remote) team, and finding meaning in your work every single day.
Trust the process - and your gut
With a steady flow of applications coming in every single day, Squared Away's process for hiring virtual assistants is now down to a science. Some prospective hires come through Hire Heroes, a nonprofit that helps military members, spouses, and veterans secure employment, while others apply directly through Squared Away's website. Qualified candidates then move through the interview process, which involves completing task-based assignments - like creating detailed travel plans or workflows in Asana - and conducting behavioral-style interviews with Opel and Penzcak. The most promising are invited to complete a rigorous training program, and anyone who passes with flying colors gets hired.
And that's definitely not everyone. "It's very selective," noted Penczak. "I'd say we're hiring probably 10% of the people who apply."
It's a process that has been honed and refined over time. "It's based on the best assistants we've seen succeed," noted Penzcak. "We started out very basic with our requirements and tightened them up as we've grown to allow for a better client match."
Michelle Penczak
Though Squared Away is a fully remote team, Penczak and her team try to connect in person regularly. In 2019, she joined a New York City fireside chat hosted by Squared Away client Callie Schweitzer.
Despite the super-streamlined process, Penczak is quick to note that her instincts still play a part in who she ultimately brings on board. "I essentially follow my gut," she said about the interviewees that make it to her stage in the process. "If I think they're going to be a really good addition to our community, then I invite them to do training." One example? Following a feeling to hire an assistant with an extremely non-traditional background - a former radiology technician. Despite her lack of previous assistant experience, Penczak said she's been an incredibly effective teammate who's now managing multiple clients.
Keep personal connections as the company grows
Penczak makes it clear that, even as the team has grown, she still has a one-on-one relationship with everyone she's hired. "I can give you the background of each and every one of them right off the top of my head," she said. "Getting to know them and their reasons for working for Squared Away is extremely important to me."
Michelle Penczak
Squared Away assistants share a virtual "high five" at the end of each team call.
Though she has hired managers to oversee teams of eight to 12 assistants, she makes it clear that anyone, at any time, can come to her or Opel with questions, concerns, or simply thoughts they'd like to share. She hosts virtual all-hands meetings every other week and is also regularly available on Slack for assistants to check in with her. (Not exactly an easy task: She lives in Hawaii and wakes up at 3:30 a.m. each day to be online when her east-coast-based assistants start their day.)
She plans to double the team next year and hopes to maintain that level of contact as the company scales. "We always want to have that personal one-on-one relationship, even if it's just a couple of times a year," she explained. "You never want your people to be a name on a list or a number on a spreadsheet."
Penczak added that this personal connection isn't just a nice to have, it's a business imperative that breeds employee loyalty. "This [military] lifestyle pulls us away from our relatives, and we still need that loving and supportive environment from people who have our back," she said. "Some don't have that community in their physical location, but via Squared Away they do … it's the core of who we are as a company."
Build collaboration into your business model
The nature of a virtual assistant role is, understandably, a one-on-one relationship with a client. But Penczak learned at Zirtual just how powerful working together as a team can be. When one assistant had an issue, others would readily support them with ideas based on their own experience.
She wanted to take this idea to the next level at Squared Away and has built what she calls an incredibly supportive network among the assistants. They're in daily communication on Slack, have regular video check-in calls, and are encouraged to reach out to each other when working on projects or tasks they're not familiar with.
Squared Away
Squared Away assistants celebrating a client's success - posing with longtime client Nicole Lapin's new book.
"They really collaborate together with different ideas for clients, which is great for them, and good for the client, because they have access to 75 different minds," she said - minds that include former teachers, attorneys, paralegals, nurses, and all kinds of corporate employees. (An example from my own life: I needed a last-minute photographer to be a source for an article, and my virtual assistant found one in 15 minutes through the Squared Away network. I can't imagine that happening so quickly if I only had access to one person.)
It's a lesson for managers of any team, virtual or not: Often, the more brains trying to solve a problem, the better. And encouraging collaboration, rather than isolation, can help both your employees and your clients get to solutions faster.
Never lose sight of your "why"
Penczak admitted that the journey hasn't always been easy, especially as it relates to her personal life. She's the mother of two sons, three-year-old Sawyer and six-month-old Jameson, who she had while in the throes of building the company.
Squared Away
Squared Away assistants enjoy great perks. This year, Sephora sent each assistant a gift card to buy self-care essentials for the military-ball season and everyday life.
"I've been so driven to make this successful for so many different families that I could have been a better mom," she said. "I still feel a lot like I should take more time to put my phone down, put my computer down, and enjoy the moment with my boys."
But what keeps her going is the story that she heard from Kelsey those few years ago - and the similar ones she hears now - about how Squared Away has changed its employees' lives. "I hear stories from our people like that almost every week," she said. "And to this day I don't get tired of hearing it because that's our mission: to employ military spouses."