Chief of Staff — the role explained

Penny Penati
4 min readMar 2, 2020

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I’ve recently transitioned from Operations Lead to Chief of Staff (COS), and when talking about this success to a lot of my friends, they were, in all honesty, quite baffled about the term. Questions I received: “What does this mean exactly?” “What will you do?” and the most comical of them all “Are you OK?”

Let’s start this off with YES! — I’m very happy about my new role. However, let’s not shy away with the fact that this role isn’t very common in the UK, let alone the startup scene. So the aim of this blog is helping to understand what exactly this role entails, what my focus shall be and who I work mostly with.

It goes without saying that any role, especially a COS one, differs heavily from company to company, whether big or small. Below you’ll find my key areas of focus.

Right hand to CEO — “Where does the CEO spend the most time on, but adds less value”

This is by far the underlying role of a COS. Talking from a startup perspective, as the company starts to grow, the CEO will inevitably spend less time involved in the nitty-gritty tasks, and consequently looks at the company from a birds-eye view. This is where the COS role comes in — helping to understand what the CEO needs to really be involved in vs. final sign off. This inherently comes from having great communication between the 2 roles, and also a deeper understanding of the business i.e. what is going on that the CEO should focus more of their time on.

An aspect that goes hand in hand to this is: preparing the various documentation for Board meetings, and internal Senior Management meetings that take place. From this, fully understanding data from all areas of the business and translating that into tasks.

Strategic Planning/Initiatives — “What does the company want to achieve this year”

The COS needs to understand the long term goal of the company, and consequently boiling these priorities down to each quarter (OKRs anyone?😉). Not only is this vital for a company, what the most crucial part of this is helping the different departments understand their contribution to the long term success of the company. Following on from this, defining and understanding the KPIs of the company, and continuous review whether the company is on track to perform its long term goal.

Project Management — “What streams are currently not being worked on, that add value to the company”

Sadly, this is where the majority of people define the COS role — “the side projects person”. Let me stop you right there, as this is definitely not the case. It is one aspect of it, but not the full extent of the role.

This facet is where the horizontal part of the role comes into play. Many of the departments are fully vertical, however, the beauty of the COS role is that it is horizontal, so you get to work with a lot of different people: tech, marketing, customer support, claims, finance to list a few!

As the company grows, there come more and more topics that haven’t yet been fully experienced, and thus it is part of the COS role to understand, analyze, make recommendations, create and streamline operations.

Other — “The Gap filler”

As a finale, the COS role, can also be “the gap filler”. As a company grows, there needs to be an understanding when is the right time to hire (a) person/people to fully focus on a specific stream. This year, I’ll be focussing a lot of my time on all things HR: different processes, feedback, reviews, etc. It’s much like the COS sets up a sort of sandbox, where you set something up and test it. Only once the company is ready to hire someone to fully focus on this stream, does then the COS hand it over to someone and they run with it and build it out to be the best it can be. Then the COS can focus on another stream and so on and so forth.

Having said all of this, this is no easy job — A COS should always know and understand what is going on at any point in time at the company. Whilst a different role, I’m very ready to kick ass as I’ve always done in my roles, and be the best COS there is.

🚨 One final point: I did my fair bit of research about the role, and would love to thank the following people that have allowed me to pick their brain over the last few months and fully understand what the Chief of Staff role entails:

  1. Sophie Donkin, Chief of Staff at Radix
  2. Josif Grace, Founder and CEO at SecureTheFile, Former Chief of Staff at Rocketspace
  3. Grace Gimson, Interim Project Manager at Facebook, Former Chief of Staff at Scape Technologies
  4. Annabel Thomas, Head of Operations at Spoke, Former Chief of Staff at Deloitte.
  5. Emily Santer, Chief of Staff at Hiscox
  6. Michael (Mish) Mashkautsan, Partner at LocalGlobe, Former Chief of Staff at National Cyber Bureau

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