"I’ve been asked to take on a chief of staff role to the CEO, but I’m not entirely sure how it will accelerate my career. I’m worried it will push me towards a generalist no-man’s-land and impact my career prospects afterwards. How should I be thinking about this opportunity?"
You’re right to be thinking critically about how a chief of staff (CoS) role will shape your career. While there’s no formal ‘graduation path’ from the role, it can be an incredible accelerant — one that steepens your learning curve, expands your strategic thinking and gives you high-impact exposure to business challenges at the top level.
In the past year, we’ve seen a surge in CoS roles (sometimes called a founder associate) as startups shift focus towards efficiency and staying lean and away from building large teams. It’s a high-leverage position designed to create more bandwidth for executives, and no two CoS roles look the same. The work can range from driving go-to-market strategy and executing special projects to tackling mission-critical problems. It’s this variability which makes some people worry it might lead to career limbo as a generalist. But in reality, it can be one of the most valuable career launchpads.
Firstly, let’s address your inner voice of doubt by looking at the common myth that a CoS role is a roadblock to specialisation. There’s a natural pressure in career-building to specialise early, but broad experience can be just as valuable as functional expertise. A chief of staff role gives you a front-row seat to multiple functions — strategy, operations, finance, product, GTM — which can actually help you choose where to go deep later, and. it allows you to build strategic thinking and execution skills that will serve you well later on in any role. Many successful executives and founders started with generalist experience before finding their niche.
A chief of staff role can be a career accelerator in many ways
You’ll gain high-impact experience at the executive level. As a chief of staff, you act as a strategic partner to the CEO — developing and operationalising their vision, joining critical meetings and informing decisions that push the company forward. Whether it’s launching a new product, entering a new market or fixing an operational bottleneck, you’ll be working on the business’s most important challenges. If a founder selects you for this role, it’s because they see you as high potential.
You can understand how a business truly operates. Unlike functional roles, a CoS role gives you a systems-level view of how a company operates. You’ll work across teams, connecting the dots between product, marketing, sales, finance and operations. This vantage point is rare and invaluable. If you ever want to start your own company or become an investor, this role is an incredible training ground. You’ll see first-hand what it takes to run a company, scale a team and make high-stakes decisions.
You will develop cross-functional leadership skills. A great chief of staff acts as team glue and knows how to influence outcomes without formal authority. Learning to navigate complex dynamics using interpersonal skills will serve you in any leadership role.
Some advice on how to maximise the opportunity
- Push for direct leadership responsibilities. Whether it’s owning a team, P&L or a major initiative, try to gain hands-on leadership experience rather than just speaking from the sidelines. If you already have a sense of where you want to specialise, get as close to that function as possible.
- Invest in relationships. While you’ll be a dedicated partner to the CEO, don’t limit your relationship building to just them. Spend meaningful time with function leaders — you may end up working with them again as a peer or boss in the future.
- Be intentional about your next step. The best way to ensure this role accelerates your career is to think ahead. What skills do you want to develop? What gaps do you want to fill? Have open conversations with the CEO so that they can help you build towards your next move. Most CoS alumni go on to become functional execs, founders, or COOs — but the career capital you gain can open many doors.
- Timebox the role. The highest learning curve in a chief of staff role typically happens within the first two years. After that, the role can become more operational or reactive unless you proactively shape your next step. Set clear goals for what you want to achieve in the role which will make it easier to know when you’ve outgrown it.
- Choose the CEO wisely. Perhaps the most important factor. Make sure this is a founder you truly want to learn from. The CoS-CEO relationship is highly chemistry-dependent, and great founders can sometimes be difficult to work for. If you don’t deeply respect and align with their vision and values, the role will be much harder to thrive in.
A chief of staff role can go in many directions and is what you make of it. It can be a springboard to some of the most impactful roles in business if you’re intentional about what you want to achieve. Rather than a generalist dead-end, it can in fact be a masterclass in leadership, strategy and execution. If the opportunity feels exciting, and you trust the CEO you’d be supporting, it could be the best career decision you ever make.
