Jody Bailey

Name: Jody Bailey

Current position: Chief Technology Officer at Stack Overflow

Bio: Jody has spent the last eight years of his nearly 30-year career on tech-leading EdTech software development teams. Most recently, Jody served as a senior product development leader at AWS, where he led the Product Management, User Experience, and Engineering teams responsible for new self-paced learning experiences for AWS customers. Jody is married and has three children and enjoys spending time with his family, travelling, mountain bike racing, sailing and listening to live music.

Hi Jody, thank you for joining us! Can you tell us about your life before leadership – what kind of roles and projects did you work on?

I had a lot of different jobs before getting into a technology role – from making dry ice and designing and installing irrigation systems to being a customer service representative for Fidelity Investments. While at Fidelity, I started working towards my master’s degree in computer science. 

During that time, I worked in a management information systems role and wrote code to generate reports for understanding and managing the schedules and performance of phone reps. This led to an opportunity in the Systems organisations where I worked as a Windows developer on a new customer service application. It was a good fit for me because I had been a customer service representative previously and understood the space well. 

How did your first leadership position come about, and was it intentional on your part? 

While at Fidelity, I was always pulled towards bringing people together to get things done, but the pivotal moment came when I was talking to one of our principal engineers. He was explaining an abstraction model and code generation tool he had developed for our systems. 

The way he passionately spoke about his work with such detail led me to realize I wasn’t as excited about abstraction models, writing code and being in the weeds as I was about helping engineers work together to deliver more business value, solving interesting problems and developing their careers.

How did you manage the transition? What came easily / what was difficult? 

My transition into management went pretty smoothly. I knew the company well and was empathetic and well-respected. I started by managing some folks who used to be my peers. They literally handed me a Dilbert cartoon about moving into management and getting a lobotomy. We all had a good laugh. 

The most challenging part of the transition was shifting from solving problems yourself to learning to motivate others to get things done. 

What was your biggest failure in that first leadership role? What made you keep doing it? 

The thing I remember most from early in my management career was a performance review I conducted with a top performer. I wanted to ensure he had balance in his life and suggested he was spending too much time working. He promptly chewed me out for telling him how to manage his work-life balance, which made me reconsider how I share information about people’s workloads. 

After being in the role for less than two years, I accepted an opportunity to be a Project Manager for my previous VP. While it was a great learning experience, I didn’t love it. It’s a hard job and can be like herding cats. After a couple of years in that role, I transitioned back to what I did love, engineering management.

Tell us a fun fact that nobody knows about you.

After graduating from college with a B.S. in Physics, I decided to go into sales. I had worked as a waiter, loved to cook, and knew someone in the restaurant sales industry, so my first job out of school was selling restaurant equipment. If you know me, the idea of me being a sales rep is kind of laughable. I like to joke that I was great at selling – right up to the point where I had to ask for money. 

What are the three key skills you think every leader needs? 

Empathy, the ability to establish trust, and good communication skills.

What have you learned about acquiring and retaining talent? 

The best way to acquire talent is to create a place where technical talent wants to work. You need to foster a great engineering culture, have interesting problems to solve and develop the careers of your engineers. Top talent attracts more top talent. 

Beyond that, in my experience, people want clarity around the goals we’re trying to achieve, clear boundaries, and the ability to operate autonomously within those guard rails. 

How do you motivate your team and manage their stress levels? 

I believe the primary factor in motivating teams is creating clear, meaningful goals that align with the individual’s goals and values. Then, it’s about supporting them in pursuit of those goals.

I do what I can to avoid putting people in situations that create unhealthy stress. There is healthy and unhealthy stress, and it’s important to know the difference. Healthy stress may come from stretching yourself and growing, and my goal as a leader is to help my reports set aggressive but achievable goals. 

However, I try to avoid creating negative stress situations, such as artificial deadlines or unrealistic outcomes. I also never want to push someone into something that doesn’t align for them. Being a good listener is key.

How do you manage your own stress levels and productivity? 

I try to focus on the factors that are within my control while recognising those that are not. I also practice journaling, gratitude and meditation – and play different sports. From a leadership perspective, I aim to build teams with people whose skills are different from and complementary to mine so we’re able to push each other and succeed as a team. 

How do you stay in sync with other parts of the business? 

Staying connected to other teams across our organisation can be challenging, especially in a remote work environment. Fortunately, we have good mechanisms in place at Stack Overflow for sharing information across the company, including using our own instance of Stack Overflow for Teams, our asynchronous collaboration knowledge-sharing platform. 

We also hold regular cross-functional meetings with other departments that discuss our progress against business objectives and our product roadmap. That’s in addition to smaller project-specific meetings. I am also fortunate that my peers in leadership represent the other parts of the organization, and we meet on a weekly basis and stay close on what’s happening on our respective teams. 

Where do you see yourself in five years’ time? 

Good question! I imagine I’ll either be here at Stack Overflow doing what I am doing or taking time off, having all sorts of fun and watching someone I helped develop do my job.

What product do you wish you’d invented? 

Maybe Zwift, because it marries my passion for cycling with technology.

Thank you, Jody!


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