Leadership Lessons Learned In the Trenches

There are three things I ask myself every day: Was I able to create value? Did I have a good time? Did I learn something new? If the answer is no to any of these, I know that I missed an opportunity for the company or personal growth. This may seem like a tedious process, but having specific goals and making sure to track progress against those goals can mean the difference between short-term success and a viable long-term plan. With readily available resources to track data, why not record, track, and learn from every success and failure my company and I experience?

This penchant for tracking and accountability has been a part of my work style since the beginning. It’s this brand of personal investment and dedication—even through hard times—that has allowed me to continue with projects, including Justworks, no matter what. Without this mentality, Justworks would not have grown 10x since 2014 and our recent funding round may not have been the success it was.

But my knack for goal-tracking was not always an innate quality. I learned, adapted, and eventually used the new skills I garnered in my journey to reach the point I’m at today. Here’s a bit about those experiences and how they’ve shaped my leadership and Justworks as a whole:

The importance of grit

“Grit” is one of Justworks’ core company values. I look for grit not only in myself, but also in each of my team members. In life, people will always face adversity and sometimes it’s possible to outsmart it. But, most of the time, it’s better to persevere and endure hardship to grow exponentially from the experience. I learned this as I paid my way through college while in ROTC, and then it was hammered home while going through training and programs in the military. If it weren’t for these exercises in grit and, eventually, leadership, I would not be where I am today.

As the CEO of Justworks, I make sure that my workforce embodies this passion. I personally interview everyone—I’ve now spoken with over 1,000 candidates—for various jobs at the company, and every hire is a commitment to employing only the very best. I always look for good people: people who have done good things for others. But, more importantly, I place a high value on candidates who can provide me with tangible accomplishments amid obstacles and hard times.

Build from what you know

The benefit of life experience  is the lessons learned along the way that can lead to better things. My entire life has in ways been training me to found Justworks. From my time as an engineer at Amazon building payment systems; to my experience as an intelligence officer in the Army Reserve where I learned about leading and motivating teams; to my founding of Adtuitive and the challenges I faced as an entrepreneur mired in hiring, payroll, and compliance paperwork; all the way to the sale of Adtuitive to Etsy where we worked with remote and distributed teams.

I lived through the evolution of the workplace. I experienced first-hand how the needs of entrepreneurs were growing more complicated and knew the infrastructure to support them was not keeping up. So, using my accrued knowledge, I developed a solution in Justworks—a simple, all-in-one platform that takes care of small companies’ foundational needs by automating payments, HR, benefits, and government paperwork. And it’s only the beginning as we continue to grow our offerings.

Understanding that we all work differently

Although finding the right talent and direction can be a challenge, it’s all for nothing without execution. Again, I took from my personal experiences—particularly my 12 years in the Army Reserve and the National Guard—and applied what functioned best at Justworks. For instance, employees here are organized into pods or self-contained units with a core mandate. The pod determines their priorities and plan of action, and the team works together to complete them.

Why do I do this? I believe that team building is orchestrating a small group to accomplish a single mission and company building is creating an environment where many teams work towards a common goal with relative autonomy. Ultimately, my and management’s role are like that of support officers, responsible for giving employees the skills they need to succeed.

In all, although stints in the process were often challenging, I would not trade any of them. I learned the real value of grit, discovered my passion, and have created a team around me that I trust to execute on our shared vision. Further, I’ve come to understand that it is not about having an idea, the right skillset or capital—it’s the culmination of all these elements that makes for success.


About Isaac Oates:

Isaac Oates is the CEO and founder of Justworks, a simple all-in-one platform that automates HR, payments, benefits, and government paperwork. He built Justworks to help entrepreneurs build their businesses and create great places to work.