Emerging Chief of Staff Career Trends

As of the publication of this blog, there were 697 Chief of Staff jobs listed on Indeed.com. For context, there were 1,593 COO jobs posted and 427 for CEO. Of those almost 700 Chief of Staff job postings, the scope of work, leadership responsibilities, projects, and even the team with which these Chiefs of Staff will work inevitably vary. Yes, the Chief of Staff role is one of the more difficult ones to define.

However, in short, I believe a Chief of Staff is a force multiplier, a right-hand partner to their respective leader who helps a Principal grow and lead an organization. Chiefs of Staff allow their Principals to stay focused on the vision, serve as a thought partner, provide strategic support, and drive initiatives forward. Long story short, Chiefs of Staff are hired to provide a result, not a service.

With that in mind, as the Chief of Staff role continues to grow as a popular position to add to a variety of organizations from tech start-ups to non-profits, to celebrities and small business owners, to family offices and global conglomerates, I see a few interesting trends emerging in the Chief of Staff career.

Founder/CEO Chief of Staff vs. Divisional/Team Chief of Staff

When I first started learning about the Chief of Staff position (and for the 10 or so years I was in the role), I usually saw the Chief of Staff supporting one Principal, generally a c-suite leader. But, times have changed and I think there are two paths emerging here.

One is a Chief of Staff who works 1:1 with the principal leader of the organization to drive their initiatives forward. And the other, a Chief of Staff who partners more closely with a particular functional team or divisional leader to provide strategic and operational leadership and project management support for the team. For example, Chief of Staff to the CEO vs. Chief of Staff to the SVP of Product. The Chief of Staff to the functional team is often called upon to act more as a strategic project manager for that division, managing OKRs, overseeing program implementation, and acting as the center point for communication.

Both are great career options and uses for the Chief of Staff role, but nonetheless, they are slightly different versions of the Chief of Staff role.

Principal First vs. Company First

Similar to the example above, depending on who the Chief of Staff is working for, two other paths emerge. One where the Chief of Staff is Principal first (for example, working for a founder lead organization or working for a private family office). Of course, the organization is a very very close second, but it’s still second.

On the flip side, some Chiefs of Staff roles tend to be more focused on a particular division or team to help implement change or grow the company as a whole. Yes, they are also, most likely, leading alongside an Executive, yet their role is for the company first, not for the individual Principal. Projects, loyalties, and priorities have to be adjusted accordingly.

Small Business Chief of Staff vs. Large Organization Chief of Staff

While Principal first or company first thinking, as well as Chiefs of Staff for c-suite leaders and others teams throughout the organization can exist in both small and large companies, I think the emerging paths here are more of a personal preference choice point for Chiefs of Staff.

Bear with me as I make some generalizations here. Small businesses allow team members a ton of visibility and the ability to make a direct impact on the company’s success. There can be a lot of opportunities for quick growth by taking on new responsibilities and broadening your skill set, since roles are not always as clearly defined or siloed. Small businesses are great opportunities for Chiefs of Staff who value autonomy, growth opportunities, and a close-knit team dynamic. Large companies often have the resources and infrastructure that small businesses do not. They provide global opportunities, additional benefits and perks that come with scale, usually more stable business operations, and options to work within specialized teams, deepening one’s subject matter expertise. And, they both have their share of negatives too!

I share this because some Chiefs of Staff will simple enjoy and thrive more in one environment over the other. Again, while the differences are subtle, Chiefs of Staff at small and large companies may be called upon to operate differently in order to achieve their respective results.

Generalist vs. Specialist

While most Chiefs of Staff tend to thrive in their role because they are generalists, I do believe that more specialized Chiefs of Staff may continue to grow, especially as we see more Chiefs of Staff joining functional teams. I think that a Chief of Staff working with a founder or a CEO will largely remain in a generalist seat, and inevitably a Chief of Staff who works with the finance, product, or marketing team will become more specialized in those areas.

The Evolving Chief of Staff Role

The Chief of Staff role is not black or white. Even my examples above have tremendous amounts of overlap and nuances that we can, and should, continue to explore.

But, I wanted to get the conversation started – both for current and aspiring Chiefs of Staff as well as those who are looking to hire them. There is no doubt that context and discernment is required when applying for, and entering into, a Chief of Staff role. But it also means opportunity!

Opportunity to work next to a founder or with the marketing team at a Fortune 50. Opportunity to flex your project management skills during a global product launch or partner with a first-time CEO as they take over their family business. Opportunity to travel and have your hands in all aspects of the business with a national author/speaker or getting laser-focused on human resource law working alongside the Chief People Officer.

As we see more and more companies hiring Chiefs of Staff, it opens up new options for individuals to find a Chief of Staff role that fit their unique skill set, experience, work-style preferences, and career growth goals. And that’s a great thing in my book!

What trends are you seeing with the Chief of Staff role?

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