The Chief of Staff role: being the ‘CEO’s right-hand’

At Maddyness, we have recently launched our job board to connect the right people with the right roles. As part of our commitment to shed some light on what these roles mean, we’re talking to professionals at the coalface. This week, we caught up with Alice Ivanoff, an interim Chief of Staff with a wealth of insight and experience.

Like most things in tech, Chief of Staff originated in the US and was common parlance over the pond before people started taking note here. As with many roles, it means different things to different people. Today, we’re focusing on its relevance for UK tech firms and startups, digging into what you do day-to-day, where it could lead – and crucially what skills you might need to fulfil your duties effectively.

The role

Alice Ivanoff is an ‘interim’ Chief of Staff (CoS), as she works part-time for two different organisations. She’s particularly useful to chat to as she not only brings her lived experience, but also wider industry insight: whilst deciding between part-time and full-time CoS roles she spoke to a huge variety of founders and CEOs about exactly what the role meant to them. She begins with the central tenet of the role: ‘you are basically the right hand of the CEO/founder’. At a basic level your aim is to support the CEO or founder directly, whether that is by saving them time through streamlining their workflows, taking notes at meetings and following up – or just being a sounding board for the whole company.

Extrapolating on the different understandings, Alice points to a useful Harvard Business Review publication detailing four different levels that CoSs can occupy – in increasing seniority and strategic insight. Level 1 is the step above an EA; typically there to operationalise and streamline work flows. They will generally oversee the CEO/Founders time, ensuring focus on the most important issues. This is primarily an administrative and operational role, but you will have oversight of the whole business even at this level.

A Level 2 CoS extends their remit to the rest of the executive or C-Suite – and engages a wider pool of stakeholders generally. They may be the communication bridge between different departments such as sales and product, and may grant access to the CEO or founder, giving back as much of their time as possible. They may be tasked with running a variety of special interest strategic projects, and maybe writing briefs and papers for the CEO or founder.

At Level 3, CoS tend to become more like thought partners than Levels 1 and 2, and is arguably where the term originally came from. You are in essence a shadow founder or CEO, vested with the authority to approve or advise the team in their absence. Alice points out that a Level 3 CoS may often be found in startups who are raising funds – as this can become an all-consuming task for founders.

This 3 tiered analysis is useful, but given its US, corporate remit should be seen as a starting point to understanding the role. Alice stresses the point that CoS roles are not necessary linear; there is no assumed progression from one level to the next in the startup world. She sums up how she operates as ‘by being the grease and the glue’ of the team. As with many startup roles, this is a highly mercurial position given your lack of departmental allegiance. Alice discusses how you will ‘yo yo around the company, going from often super operational – almost administrative tasks – to running through the financial projections for the year ahead’.

Skills

In a startup context, Alice describes the 3 most important skills you will need to thrive as a CoS. Unsurprisingly, given the almost limitless remit she stresses a generalist mindset – someone with an operational focus, and action-bias. Second is a sense of curiosity: you’ll be interacting with people outside your team and company on a daily basis, and so it’s important you can build relationships instantly and take an active interest in all conceivable areas of the business. You will be given access to – and be expected to attend – meetings cutting across every business function, and so it’s important this motivates you and that you are adaptable.

Finally – and Alice qualifies this as more of an opinion than accepted logic – is your need to be comfortable with the numbers. Alice puts this requirement down to the fact many startups will hire a CoS when they are yet to have a head of finance (or head of ops) and therefore will need to be familiar with financial strategy.

Why should you become a Chief of Staff?

In Alice’s words, you find yourself ‘in a privileged position’ as CoS. Her enjoyment in the role comes from the access-all-areas nature of the role, and particularly your proximity to the founder or CEO. She explains that the role can essentially be a masterclass in running a startup – you can witness first-hand how the founder builds a team and company culture and trust; gets investment; how they think.

Closely related to the roles of Founder Associate (which would likely be comparable to a Level 1 CoS) and Head of Special Projects, this role is therefore great for anyone with founding ambitions themselves.

If this sounds like just the ticket, then check out our jobs board here – where there are many Chief of Staff roles featured.