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Heroes Among Us: “Command and control are an illusion” With Isaac Oates CEO of Justworks

Command and control are an illusion. Many people have the misconception that all military activity is tightly controlled, that generals give orders and soldiers take them. My experience was much different — I was surprised by how much autonomy there was in low-level units. By standardizing how we operated, we were able to decentralize, making it easier […]


Command and control are an illusion. Many people have the misconception that all military activity is tightly controlled, that generals give orders and soldiers take them. My experience was much different — I was surprised by how much autonomy there was in low-level units. By standardizing how we operated, we were able to decentralize, making it easier to respond to situations quickly. In today’s operating environment, soldiers need to exercise extraordinary judgment, often without direct support from higher headquarters.


As a part of my series about “Life and Leadership Lessons Learned in the Military”, I had the pleasure of interviewing Isaac Oates. Isaac is the Founder and CEO of Justworks, the HR technology platform that helps entrepreneurs and businesses grow with confidence by giving them access to benefits, payroll, HR, and compliance all in one place. Before founding Justworks, Isaac served for 12 years in the National Guard and Army Reserve as an intelligence officer, where the importance of an unshakeable team and a focus on people became clear to him. He began his professional career working as a software engineer at Amazon, eventually leaving to build his first startup Adtuitive, which was acquired by Etsy in 2009. At both Adtuitive and later Etsy, where Isaac led the HR and payments group, he recognized the system was broken. Frustrated by paperwork, exorbitant costs, and endless hours spent on administration instead of his team, he came up with the idea for Justworks in 2012. Isaac holds an MBA from Cornell University and a BS in Computer Science from the University of Illinois at Urbana-Champaign. He Lives in Manhattan with his son James.


Thank you so much for doing this with us! Can you tell us a bit about your childhood “backstory”?

I grew up with my mom and moved around a lot as a kid. I was shy and spent a lot of time dabbling in computers and electronics. I learned to program when I was 10 years old and enjoyed being able to create something out of nothing.

And what are you doing today? Can you share a story that exemplifies the unique work that you are doing?

I run Justworks, an HR tech company with a team of 450 people in New York. We help entrepreneurs and businesses grow with confidence with access to benefits, payroll, HR, and compliance support — all in one place. We make it easier for them to hire and pay people and to take care of their teams, attract and retain talented people, and we save them a lot of time. I love that we play a small role in what each of them is doing. Just recently, the founder of the Global Autism Project, a customer, came to our all-hands meeting to share what they are doing, and it’s so cool to be part of that.

Can you tell us a bit about your military background?

I enlisted in the National Guard when I was a senior in high school. I thought it would be a great way to help my community in times of need, which was something I had gotten some experience with as a volunteer firefighter. I spent a total of 12 years in the Guard, which was “part-time” (one weekend a month and two weeks a year) aside from training. I spent most of that time as a military intelligence officer.

Can you share the most interesting story that you experienced during your military career? What “take away” did you learn from that story?

Near the end of my service, I was a unit commander in Syracuse. One of my soldiers was this kid, maybe 19 or 20, who wanted to go to college but didn’t have any role models. He enrolled in college at one point, which the military paid for, but then he dropped out because he didn’t think he could do it. The truth is, no one around expected him to be able to finish school, so he dropped at the first opportunity. It was such an important reminder that we rise to the level expected of us. At Justworks, we’re driven to help people prove to themselves and others that they are capable of achieving new and amazing things.

I’m interested in fleshing out what a hero is. Did you experience or hear about a story of heroism, during your military experience? Can you share that story with us? Feel free to be as elaborate as you’d like.

In the army, you often hear the expression “don’t be a hero.” What makes the military work is people working together to accomplish a common goal. It’s not about the soldier, it’s about the unit. When someone stands apart and does something on their own, that often creates more risk than it’s worth.

Based on that story, how would you define what a “hero” is? Can you explain?

Heroism and leadership are two peas in a pod. Inspiring others to do something great, especially in the face of danger or adversity, is nothing short of heroic.

Does a person need to be facing a life and death situation to do something heroic or to be called a hero?

I don’t use this word.

Based on your military experience, can you share with our readers 5 Leadership or Life Lessons that you learned from your experience”? 

Lead through questions. As a young officer, I was often leading people who had much more experience than me. In some cases, I was leading people who had been in the army longer than I had been alive. When we would discuss our plans, I figured out that asking lots of questions would both help me learn and help them see what I saw while respecting their experience.

Take responsibility for your own career. The military is built on a system of people constantly rotating through different positions, typically 9–18 months. This is an amazing opportunity to get broad exposure to many different roles, but it also means that there aren’t other people around to look out for your career. By learning how the system worked and advocating for myself, I was able to take on some unusual assignments where I was able to learn a lot.

With rank comes responsibility. Early in my military career, I didn’t understand how hard senior people worked to make the entire thing come together. I remember when I started my officer training program and was informed by my unit commander that I would need to start spending a lot more time with my unit. Not for pay, and it wasn’t optional. Those were the meetings where we would plan our drills, etc. As I progressed, the expectations just kept increasing.

Command and control are an illusion. Many people have the misconception that all military activity is tightly controlled, that generals give orders and soldiers take them. My experience was much different — I was surprised by how much autonomy there was in low-level units. By standardizing how we operated, we were able to decentralize, making it easier to respond to situations quickly. In today’s operating environment, soldiers need to exercise extraordinary judgment, often without direct support from higher headquarters.

Embrace your leadership style. During my officer training, most of my fellow cadets were uptight, to say the least. I began to conclude that I would have to match this style to be successful. Then I found an old manual about leadership that compared and contrasted the styles of many successful military leaders. I realized it would work better to just lead in the way that I was most comfortable. This bore out through my career — I discovered that each of my peers had their own style, and the more comfortable each of us got with this, the more effective we could be.

Do you think your time in the military helped prepare you for business? Can you explain?

Military service absolutely helped me become the leader I am today. I learned about balancing the need to accomplish your mission with the welfare of your soldiers — “mission first, people always.” I learned about how a massive and complex organization can be incredibly effective, even in the face of rapid change and an unstable environment. I learned about how important it is to get the little stuff right so that you can focus on the big challenges. I learned that people from all walks of life can come together, accomplish something, and then go home. I saw a recruiting poster once that summed up the experience better than I ever could: “First you are a part of it, then it becomes a part of you.”

As you know, some people are scarred for life by their experience in the military. How did you struggle after your deployment was over? What have you done to adjust and thrive in civilian life that others may want to emulate?

I never deployed to a combat zone. I am indebted to my friends and colleagues that did. Some lost their lives, others had experiences that will change their lives forever.

Are you working on any exciting new projects now? How do you think that will help people?

I have been focused recently on strategic planning. This is a luxury I did not have in the early days of Justworks because we were focused on day-to-day survival. It is fun and gratifying to look into the future and plan against it. It is even more fun to talk with the team about it, to let them know what is coming our way and how we will be able to work together to seize opportunities and take on challenges.

What advice would you give to other leaders to help their team to thrive?

Know yourself. Leaders who are self-aware can play to their strengths and manage their weaknesses. Over time, organizations imbue themselves with the characteristics of their leaders, so you might as well know what you’re dealing with.

What advice would you give to other leaders about the best way to manage a large team?

You need to be intentional about the communications architecture of your organization to ensure that it remains effective, even as the organization grows. What worked with 20, 50, 200 and 500 people are all different. Small teams can be pretty casual with how they communicate; you have to be intentional with a larger team to ensure that everyone is getting the right context and information.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I have been fortunate to have many mentors in my career who have gone out of their way to help me grow and develop. One person who I have been working with for nearly ten years now is my coach, Jerry Colonna. Amongst other things, he has helped me see how I might be complicit in creating conditions that I don’t want. What starts as “this person is driving me crazy” often resolves as “I’m meeting an unseen need by having this person behave that way.”

How have you used your success to bring goodness to the world?

Having an organization like Justworks is a tremendous platform to help people realize their potential. We support entrepreneurs, teams, and families in pursuing their passion, whatever that may be. I’m also

proud of the workplace that we have created. I think we are a fantastic place for people to launch their career or take it to the next level, and we provide more support than most organizations so that our employees can grow and take on leadership responsibilities if they so desire.

Service has also become an increasingly explicit part of our culture as we’ve grown. For example, this March, we ran an event where nearly all of our employees volunteered in small groups as charities and causes around NYC. It’s not just about doing something good, it’s about doing something good together.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I would love to see a broader focus on leadership development. While the military offers top-notch leadership programs, I think everyone has the capacity to lead and developing core skills like self-awareness and self-mastery in educational and commercial settings would be a boon for our nation, both in public and private life.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

The Outward Bound motto is “If you can’t get out of it, get into it.” I think most of us avoid the hard stuff or go around it, often subconsciously. This quote has helped me explore some of the hardest things, like how my childhood or upbringing might affect my company, for better or worse.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

I would love to meet former President Obama. Coffee would be fine. I’ve always appreciated his optimism and willingness to take the high road. We need more of that in public life.

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