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  • Operator Sessions
  • 29 November 2022
  • 7 min read
  • Words: Northzone

Operator Focus: What does the Chief of Staff role entail?

The Chief of Staff role has been the kept secret of successful tech entrepreneurs for a very long time. Thousands of companies have since then copied tech giants in building more efficient executive teams, that ultimately make the CEO successful in their role. 


Our portfolio companies are no strangers to this trend so, we spent some time with three world-in-class Chief of Staff’s to dissect what the role entails and how founders can leverage these roles to build successful companies. Martina Stokes from Fiberplane, Evelyn Mackinnon at Wagestream and Philipp Richter working at leading HR company Personio shared their insights with us. Their experiences offer an overview to the role’s purpose; its challenges; and what advice they wish they’d had at the beginning. 

What does it mean to ‘make the CEO successful in his role’? Martina Stokes describes it as ‘making the CEO more efficient’, advising, “Think about what projects make sense for the CEO to own. Set goals, do the labour around that, present it to the CEO, get their opinion to make some adjustments and finally, roll it out. Basically, you need to do a lot of the grunt work to free up their time so that it can be spent wisely on other things.” 


It is clear that the COS role will look slightly different depending on the company. One must align, in conjunction, what is needed from the CEO with what is needed from the COS for the stability, success and continuous growth of the company. The overview of the role consists in seamlessly dealing with executives, by assisting throughout the decision making, program management and initiative implementation stages and acting as a liaison between them and the rest of the structural organisation. 


The world’s increasingly stressed conversation on the importance of employee well being has stemmed from the difficulties in retaining top talent. This relates as another crucial part of the Chief of Staff’s role is ensuring a positive company climate. One of the ways Evelyn Mackinnon ensures this is by, clearly communicating business objectives so that everyone understands the importance of their individual contribution. Alongside this you need to create channels for people to share their biggest challenges so you can offer support along the way.”


What qualities are crucial for success in the position? And how does one end up in the role?


All Chiefs of Staff are unique, but we found some common denominators: one must be a Jack of all trades; have excellent communication and social skills; a good dose of humility and humour; be an organisation wizard with a good sense of priorities and; an unmatched synergy with the CEO. The three COS’s backgrounds prior to their roles similarly involve positions which honed these qualities.


Prior to becoming a COS, Martina Stokes was Head of Community in a co-working space for tech companies. She was surrounded by and managed the communities of companies at all different stages, from different places and from diverse teams – a fast paced environment. Philipp Richter pursued his passion for business and computer science, became a consultant for digital and data driven business models which confirmed his love for tech, working in teams and how he strives as an operator. 


Evelyn Mackinnon also comes from a trained background with over 15 years of experience working with a full range of startups. From seed through to IPO, acquisitions and series A’s, B’s and C’s. Evelyn says, “a good Chief of Staff needs to constantly wear a lot of hats. That experience in high growth startups, doing a lot of different positions and being content rolling up my sleeves if it means things get done, is what brought me into this role today.”


To become a Chief of Staff there is no doubt you need experience, talent and all the above but at the end of the day the conclusion is that creating a trusting, transparent partnership with the respective founder is imperative. 


The temptation of hiring a Chief of Staff too early – or the mistake of too few too late? 


Early stage startups are infamous for the magnitude of ongoing workload that needs to be done. The reality is that the workforce and budget is scarce, and time is of the essence. As a company grows, the amount of work and time doesn’t change but there is more monetary and personnel support. Hence, hiring a Chief of Staff early on would surely be advantageous?


Philipp Richter discussed some of the dangers that come with this and believes that although it’s different for every organisation, he would suggest not hiring a COS until a company has reached roughly the 100 people mark. He mentions the temptation of having the COS run critical programs and initiatives which really should be owned by other parts of the organisation. It’s important to build critical functions properly early on, which you are more prone to do if you don’t have the luxury of a COS running these programs for you. Further on the exact timing to poach your dream chief of staff, Philipp adds that founders should “experience things [themselves], you need to roll up your sleeves and be very hands on, to later delegate and distinguish advantageously.” 


On the other hand, Martina Stokes was one of the first seven employees at Fiberplane and describes herself as the first ‘non-product’ employee at the company. Her personal experience is an example of how there really is no universal ‘right time’ and that it truly comes down to properly analysing what your company needs. She shares, An organisation is not only a product, the people in it are just as important. You can’t have a business without a team, and a Chief of Staff can help get things up and running in that domain by laying the groundwork for hiring, onboarding, and other people processes.


In a nutshell, you should determine whether your business needs more focus on people management and whether the CEO is spending too much time on inefficient things ahead of hiring such a role. However, always keep in mind what boundaries need to be set and challenge how effective the relationship you are building with the Chief of Staff is.


How does the role change and adapt throughout the business’ growth stages? 


Once again, the fundamental principle of the role, that will never change, is making the CEO successful. However, what that means as a company grows, changes as the context becomes a different picture. Philipp Richter gave us a basic outline of what this might look like throughout the stages but again, every organisation is different. At an early stage of a business, as mentioned before, there’s an abundance of work and the workforce is scanty so, everything is very hands on. 


As a COS you’ll need to bridge gaps in the organisation, take on any topics that don’t have an owner and really play the Jack of all trades card. Once you start to bridge those gaps and the company grows, the role will shift from smaller tasks to focus more on special projects, liaising with the CEO. And finally, once the company is more structured and has effective operating systems in place, the COS role becomes more of a stand-in role for the CEO. 


The best advice from one Chief of Staff to another.


We asked each Chief of Staff to share some advice they wish they had at the beginning of their journeys. Much of what they had to say tied in with the above, specifically revolving around the qualities you need to have and a lot of their advice coincides with each other. 


We picked three snippets we believe are crucial:


Martina Stokes, COS at Fiberplane, “Network and talk to other Chiefs of Staff. Connect with people that are at a similar stage as you or even at earlier stage companies in order to assess and learn from each other’s struggles as well as successes. It’s important to also connect with Chiefs of Staff from bigger companies so you can scope out how the role might evolve and be prepared for it.”


Evelyn Mackinnon, COS at Wagestream: “You have to be very pragmatic, and you have to be happy to reprioritize. Even if it’s something you spent a lot of time working on, you have to be able to toss it to the corner and say this isn’t right for the business.” 

Philipp Richter, COS at Personio: “It’s a very impactful and exciting role but, it’s also a role that operates mostly behind the scenes, leading from the shadows and you either strive under these circumstances or you suffocate because you don’t get the attention and the appreciation that you need. Everyone is different, there’s no judgement but it’s important to be honest with yourself, whether this suits you or not.”