In many cases, they’re two wildly different skillsets. There is for sure a category of Chief of Staff, which the Executive Assistant role fits into nicely - but it’s not the default and it’s so misleading. 

The majority of Chief of Staff roles are highly strategic - I’m not talking ‘be proactive’ strategic - I’m talking about understanding how industry-relevant mechanics work, technology, transformation, M&A initiatives, legal, corporate policy - the list goes on. 

For an Executive Assistant who wants to step into the Chief of Staff role, is likely going to have to accept two things: 

1. This is a career change - it’s not just a step up. 

2. The roles you’ll be suitable for will likely be ambiguous and operational - less strategic. 

With the last point, you may think a Chief of Staff is all about strategy - which for corporate level Chiefs of Staff, this is true. However, there is a category of Chief of Staff which sits firmly in the ‘ambiguous’ and ‘operational’ category - these are Start-up CoS, Founder CoS, and HNW CoS. 

Honestly speaking - these are some of the lowest paid and less technical Chief of Staff roles. 

They’re still remunerated well, against the Executive Assistant role - but the responsibility is more ‘wear multiple hats’ and become the ‘Chief of Everything’. In some cases, it may even be a mistitled CoS role entirely (more admin-focused, low pay, grand title).

These roles are few and far between. If you’re an exceptional Executive Assistant, it’s these you should be aiming for. These roles are the exception, not the default. 

What the other category of Chief of Staff looks like. 

There’s a whole different world out there, which many on LinkedIn seem to miss (mostly due to the echo-chamber nature of LinkedIn showing you content from people similar to you) - it’s the truly strategic Chief of Staff. 

These are the roles which are often compensated north of $250,000 - sometimes as high as $500/600k plus benefits. 

These types of roles usually bring technical skillsets or experiences to the table. For example, it might be a CoS who leads the Office of the CEO in a publicly listed org, it might be a CoS with a background in PR/Comms, a political CoS, an investment CoS within a global investment bank, a big law CoS - through to functional Chief of Staffs focused on specific niche problems, or growth Chief of Staffs supporting business growth. 

These are career-track roles - not lateral moves. 

Going further here - an example of a Chief of Staff within an global Asset Manager- this role could be tasked exclusively at reducing the Assets Under Management reporting timeline, across a firm with tens-of-thousands of employees, strategies, and assets. Reporting directly into the CEO, responsible for implementing technology and transformation, understanding complex financial reporting, and using their gravitas to ensure the right levers are pulled both internally and externally. 

Another example could be a Chief of Staff within a global law firm, responsible for the logistics and coordination of the executive committee, managing multiple partner priorities, and understanding the commercial needs and political climate of the firm, across partners, and decisions being made. This role requires technical ability and experience very few Executive Assistants would ever be exposed to. 

A final example might be a Chief of Staff working within a Fortune 100 firm - overseeing a sizable Office of the CEO - responsible for turning complex upstream data into actionable insights for the CEO to act on. This role has a fundamental requirement for the CoS to understand what this data actually means, what’s important, and what the outcome of such information could be. 

My point here - the above examples aren’t simple CoS roles - it’s a position with a $600k comp attached to it. The below scatter graph provides some context. 

So what does this mean for Executive Assistants who want to progress? 

I get the excitement. For the first time, there's a C-level title that feels within reach. That's exactly why this conversation needs to happen.

But be honest with yourself about which quadrant you're actually aiming for - and which one you're actually qualified for. There's no shame in the operational CoS path. For the right person, in the right organisation, it's a genuinely exciting role.

But go in with your eyes open.

The Chief of Staff title has become a catch-all - and LinkedIn has made it worse, serving you content from people who look like you, think like you, and are navigating the same stretch of the market you are. The $500k CoS isn't posting career advice on LinkedIn. You're not seeing that world because the algorithm isn't built to show it to you. There's also a lot of noise from people in the market who have never actually seen the 'other side' of the CoS market. 

The role you're being sold and the role that actually exists at the top of this profession are, in many cases, completely different jobs with completely different entry requirements.

If you're an exceptional EA with real operational instincts - chase the ambiguous, founder-facing, wear-every-hat CoS role. It can be a massively rewarding role if you’re wired that way. 

But don't mistake that for the ceiling. And don't let a grand title on a low-paying and mistitled role convince you that you've made it to the other side.