From Software Engineer to VP of Engineering: Leadership in Action at Cheesecake Labs

Two years ago, Cheesecake Labs had a team of around 45 Cakers — but we are growing fast. Our board knew that to keep pace with our growth we needed to proactively develop leaders. Enter Natam Oliveira.

Natam joined Cheesecake Labs as a Software Engineer in 2018. He quickly started moving up the ranks; today, he is the VP of Engineering.

How did Natam go from Software Engineer to VP?

He became a leader at Cheesecake Labs with the help of our leadership development programs — and then he helped improve them! Here’s what his journey looked like from new Caker to VP.

Seeing the potential

Just six months after joining us a Cheesecake Labs, Natam became a Chapter Lead. In his new role, he was responsible for overseeing several different teams. And during this time, he was mentored by Cheesecake Labs’ former COO, Bernardo Smaniotto.

He saw excellent leadership potential in Natam and suggested he take the time to work on leadership development to become a Senior Engineer able to lead others in the team. 

A new kind of leadership training

At the time, we had an existing leadership program in place. But in Natam’s case, Bernardo saw the opportunity to shake things up and take a new approach. So with my help (Hi, I’m Carol, the CPCO [Chief People and Culture Officer] here at Cheesecake Labs), Natam started down a new path to leadership. 

One-to-one coaching

For the next eight months, Natam and I had one-to-one coaching sessions to help him develop his leadership skills.

When he first joined Cheesecake Labs, Natam noticed our focus on soft skills and empathetic leadership. And during his leadership mentoring, he learned the difference between being a boss and being a leader.

To help make sure he stayed on the leader path, Natam and I worked on vital skills like public speaking and storytelling, vulnerability, creativity, finding a sense of purpose, and courage. 

To make the most of our time together, I looked for models and frameworks for each skill and then gave Natam mini-challenges to work on in between sessions.

We used things like SMART goals to guide the learning process. These goals are specific, measurable, achievable, relevant, and time-bound. I chose this method because it made it easy to keep track of Natam’s development goals and progress. 

Now, we didn’t jump in and try to develop every skill at once — that would have been overwhelming. Instead, we chose three primary skills to work on first, knowing that developing those first skills would later help Natam develop others.

And the process was incredibly collaborative. Natam had the freedom to set his own goals and how he would measure his success. 

It was a lot of work, but soon Natam was meeting all his goals. And then, another shift in the company left him with even more responsibility. 

Another Chapter Lead left, and Natam was put in charge of two Engineering areas. His new leadership skills were put to the test. Soon, Natam was made VP of Engineering and had a seat on the board. 

Now a part of Cheesecake Labs’ senior management, Natam noticed an opportunity for improvement.

Sharing responsibility

As he gained more experience and responsibility, Natam noticed that Cheesecake Labs was growing so quickly that we needed to shift our internal leadership strategy.

Instead of having one person in charge of large teams, Natam suggested to the board that each engineering team needed “mini-leaders” to help keep things running smoothly.

He wanted to make sure no one person was overwhelmed by their responsibilities. As the company grew, he noticed that Cakers in management positions saw their list of duties grow too. 

This idea led to the creation of our Tech Lead roles and has helped us redesign our company structure. 

The student becomes the teacher

Instead of looking outside the company to fill these new Tech Lead positions, Natam and I decided the best thing to do would be to look internally.

We started choosing Cakers with leadership potential and set a plan to mentor them on their journey to becoming Tech Leads. 

Knowing how helpful his own mentorship was, Natam got to work creating a mentorship program for the Tech Leads in training.

This new program followed the same structure as Natam’s training. He and I developed the skills essential to the Tech Lead role and then used models and frameworks to help each Caker work towards their individual goals. 

“I want to work with people smarter than me.”

This new approach came directly from something Natam often says, “I don’t want to hold all the responsibility. I want to work with people smarter than me.” 

Where a boss might want all the power to themselves, a leader recognizes that every person in the room has something unique and valuable to contribute. And Natam knew there were Cakers eager to share their voice and become valued leaders.

He thought this was the perfect chance to test this new leadership development process to see if it worked with Cheesecake Labs’ overall strategy. 

And it was a rousing success! After starting with two Tech Leads, we now have eight!

The journey is half the lesson

This whirlwind journey from Software Engineer to VP of Engineering wasn’t always easy, and Natam spent lots of time learning new skills and honing existing ones. In his pre-Caker life, Natam ran his own company.

o he already knew how to be responsible for multiple things. But joining the Cheesecake Labs team made him realize that sometimes it’s best to share responsibility across many people — after all, many hands make light work!

People make the cake rise

And learning how to fit in as a slice in the larger cheesecake wasn’t always easy for him. Working with such a diverse group of people challenged Natam to get out of his comfort zone — which is exactly what he now recommends other Cakers do. He says:

“If you see something you want, challenge yourself to get out of your comfort zone and go after it.”

By working with all kinds of people, every Caker gets the chance to learn about other people, cultures, and experiences. And this knowledge can only make us a better team. 

Learning when to delegate

The company has grown — we’re over 100 Cakers now and adding more daily! With so many people joining the Cheesecake Labs ranks, Natam has had to learn how to be a leader when he doesn’t know each team member closely.

He’s learning how to spread the Cheesecake Labs culture without overextending himself while still being available and accessible to everyone in the company. He’s had to learn to delegate and find ways to incorporate the Cheesecake Labs values into everything he does to keep our culture alive. 

The future of leadership development at Cheesecake Labs

We’ve grown unbelievably quickly and have been thrilled to welcome so many new people into Cheesecake Labs. And with that kind of growth comes lots of changes, shuffles, and restructuring. We started with around ten leaders in the company, and now we’re working towards 35.

Our company cake has three main tiers: The board, leaders, and teams. And we stand by the fact that we’re all part of the same cake — every part contributes to the whole. That’s why we are committed to a flat structure. 

And most of our new leaders have come from within the company and are helping us keep the development ball rolling. Our leaders run monthly mentorship programs. They help new Cakers choose their development goals on day one and guide them through developing them.

We’re running a new leadership program for project managers, and we’ve got lots of other plans in store!

Ultimately, Cheesecake Labs is full of leaders, each in their own way. And every person works hard to manage and foster our culture, keeping everyone motivated along the way. 

Natam’s journey is a prime example of this culture in action — if you invest in people, they’ll give you back that investment tenfold. 

And it’s not a one-way street. As Natam says, “Don’t wait to become a leader.”

Anyone at Cheesecake Labs can be a leader, whether it’s your first day or you’ve been here for years. 

If you want to see how you can help us keep building a company full of leaders, take a look at our open positions and check out our post “Why work in a top 10 mobile app company?”, talking about what it’s like to be a Caker!