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Engineering Investment and Business Alignment

The Rising Popularity of the Chief of Staff in Engineering

At Jellyfish, we’ve noticed a rise in the number of engineering teams that are leveraging a Chief of Staff of Engineering. While each company approaches the role in a slightly different way, the core mission of this person is to enable the successful execution of the engineering leader’s objectives. And after recent conversations with several Chiefs of Staff, it’s clear that they’re invaluable to their teams. 

In this ongoing series, I’ll highlight key snippets from my conversations that demonstrate how organizations are leveraging Chiefs of Staff to help maximize operational efficiencies within their engineering teams. 

My first conversation was with Freddy Munoz, a recent Chief of Staff to the CTO at Compass. Freddy had a wide variety of background knowledge about the role’s history, and he was more than willing to share some of this wisdom. After two years in the role, Freddy has gone on to lead Compass’s Technical Program Management team. In this post, I’ll highlight a few of his key insights. 

Why CoS is on the Rise

The Chief of Staff of Engineering role is gaining popularity. While many leaders don’t fully define the parameters of the role from the onset, high-performing engineering organizations that maximize the value of the role have a few core responsibilities in common. Freddy explains:

“The role of the Chief of Staff is relatively new, but there is a recent popularization of the role. It’s been around just for a couple of years, and it is still pretty much undefined. It is the type of role that organizations do not take a lot of time to define. 

But engineering leaders are starting to understand the value of having someone that can be a sounding board for them, that can drive an organization forward, and that can be the right hand for that leader in terms of execution. They can not only be someone that helps manage the business, but also the person that helps solve random problems that arise. Depending on the size of the organization, there are different archetypes for the Chief of Staff. For example, companies like Microsoft or Amazon might have Technical Advisors to SVPs (or the CEO). Technical Advisors function slightly differently from a Chief of Staff for a company like Dropbox, or Compass.”

Acting as a Representative for the Engineering Leader

Compass has historically hired Chiefs of Staff of Engineering with extensive technical backgrounds, and, in Freddy’s view, it’s nearly impossible to do the job without prior technical experience. Chiefs of Staff are asked to be problem solvers and the primary confidants to the highest levels of engineering leadership. In his view, it’s important that they understand the exact details of what teams are challenged by so they can translate those challenges accurately to all levels of the organization.

“There is a lot of administrative work that is involved in being the Chief of Staff, such as managing projects, managing talent, etc. But it’s also critical for a Chief of Staff of Engineering to understand the technical subtleties of the organization. They need to be able to understand the technical decisions that are being made by other people, and be able to report that to the Head of Engineering.

The Chief of Staff is the right hand of the leader and many decisions are delegated by proxy to the Chief of Staff. For that reason, you need to know very well how technology is applied. If your job is developing software, how do we develop software? What is the skill set that we need to develop software? What is the role of a quality assurance engineer? Are we operating in the cloud? How much money are we spending in the cloud? Why haven’t we migrated to Kubernetes yet? Or, if we migrated, what is the next step?

As the Chief of Staff, you need to have mastery of all those questions and more that will come.” 

The Chief Problem Solver to the Head of Engineering

In addition to being the right hand to the engineering leader, it’s clear that the most effective Chiefs of Staff are the chief problem solvers of the engineering organization. In companies that leverage Chiefs of Staff to their fullest potential, they are frequently tasked with clearing the roadblocks that prevent engineering from doing their best work.  

“Your boss can come to you at any point in time and say, ‘We have this problem with this cost. It’s getting out of control for this particular group. Can you please take a look at it?’ 

Your job as Chief of Staff is to fix problems and to make sure that the organization is operating better than the day before. Maybe there is a team that’s not operating very well and it’s creating an attrition risk. Or, maybe you have an organization that’s spending way too much money on infrastructure, and you need to dive deep into how they pay for hardware. In each of these examples, you need to see the problems firsthand, analyze them, and find a solution. 

The good thing about being Chief of Staff is that nobody is going to say no to a meeting with you. People will tell you about their challenges and they will listen to you. That puts you in a unique position to be able to understand what people want and be able to help them work on reaching consensus and aligning on goals that will help them move forward.”

As engineering organizations grow and become more complex, many engineering leaders require someone that they can trust will help solve their operational challenges as they arise.  Freddy was able to become an invaluable asset to Compass’s engineering organization, often functioning as a proxy to the engineering leader and master problem solver for key challenges. In our next post on this topic, we’ll chat with other Chiefs of Staff to understand their approach to optimizing operations for their engineering teams.