The Chiefs of Stuff: Conversations with the Right-Hands of Founders
Are you ready to dive into the hottest role in the startup world that has its roots in Silicon Valley?
Not too long ago, I wrote about the rise of the Founder Associate in an article titled “The Emergence of the Founder Associate.” This role captures the essence of being the founder’s right-hand operator, similar to a trusted “consigliere” in The Godfather. I thought this couldn’t get any better — yet I was wrong.
As I delved deeper into the startup landscape, I stumbled upon a more experienced counterpart, the Chief of Staff, or as I like to call them, the Chief of Stuff. Interestingly, the CoS role has already made its mark in the startup world for at least a decade in Silicon Valley, drawing inspiration from stars such as Sheryl Sandberg, who was pivotal at Facebook, and Brian Rumao and Ben Casnocha at LinkedIn, all CoS to the respective CEOs. Now, the role has crossed the ocean and is experiencing serious momentum in hubs such as Berlin, London and beyond. Yet, what does a Chief of Staff do, and how do you become one? If these questions make you ponder, then you have come to the right place!
To help clear away any headaches and answer these questions, I’ve interviewed four rising stars across Europe who work at some of the most exciting venture-backed startups. Together, we’ll unravel the mysteries, discover the responsibilities, and explore the path to becoming a Chief of Staff.
Filip Mark, Passionfroot (Raised €3m from Creandum and notable angels)
Simba Kaur Deu, Vital (Raised $3m from Point Nine, 20VC and YC)
Jasmin Heimann, Procuros (Raised $10m from Point Nine and Creandum)
Jonas Morgner, TradeLink (Raised €15m from Point Nine, Insight Partners and Fly Ventures)
#1 Filip Mark (Passionfroot)
In 60 seconds, how did you find your way to become the CoS at Passionfroot?
During university, I knew I wanted to get into startups and venture capital and tried to set up paths in that general direction. This led to joining Bain for three years, working on Private Equity and Strategy projects with a technical focus, and then a period at EQT before ultimately making the full jump into a startup. After previously having been in touch with the wonderful team at Creandum, I was introduced to their portfolio company, Passionfroot. Right after, Jens Mannanal, the co-founder, contacted me, and a few weeks later, I was on a flight to Berlin. I never actively planned to be a CoS; instead, my goal was to gain experience building in the early days of a startup.
How would you describe the CoS role?
The title CoS has become somewhat enigmatic, as the role can encompass so many different things and means different things in different companies. My impression is that the role is similar to an extension of the founder, like a Swiss army knife, across the company. As the company grows, the role will become more centralised. However, in early-stage startups, the role means working across everything and getting things done.
What are some examples of projects that you are working on?
I mostly work on things that are aligned with my previous experiences, such as growth, operations, and some product development. For example, I am currently building out our business operating system to build a business before we even have a product in place for that business — giving us a running start once productised.
What are the characteristics of a great CoS?
I think you’d first need to ask our founders if I am great (laughs). Overall, being agile is great, which translates into being able to take on a large variety of projects. Second, you should be comfortable with re-skilling, as you will need to do things that you have never done before. Third, being a team player is important. In the title, it says “chief,” but that’s just window dressing — pick up the tasks that bring the company forward — even if they’re unsexy. Lastly, vitality is crucial, which means bringing high energy to everything you do and setting an example by having a positive attitude at the company.
What skills are crucial as a CoS?
I believe that regardless of where you end up, having prior experience in a fast-paced environment where you have to get things done is helpful. Overall, you need to be prepared for things to be different from what you expect. For example, we currently do not have anyone in a full-time marketing function, so over the past two months, I’ve learned how to do motion design and product animations. I never anticipated doing that at Bain/EQT, so keeping an open mind and constantly learning new things is crucial to the role.
Any advice on how to get into a fast-growing startup as a CoS?
I believe that startups who prioritise hiring are always on the lookout for great talent, even if they don’t need someone at the moment. But, they will eventually need someone after six or twelve months. For example, at Passionfroot, we keep a list of ten candidates that we would love to hire as we grow.
In short, the best way to get your foot in the door is to contact the founder directly on LinkedIn and express your interest in joining the company — it shows you’re committed. Founders love to see that someone is proactive and passionate. This approach also helps startups as traditional recruitment can be tedious and costly. It is a true win-win for all parties involved.
#2 Simba Kaur Deu (Vital)
In 60 seconds, how did you become a CoS at Vital?
I used to work at a generalist VC fund called La Famiglia. In VC, I spent a lot of time getting to know founders and realised that a CoS role could be a great opportunity to get exposure to the C-suite, learn how functions within a company are built from scratch, and understand how decisions are made through different growth stages.
I also wasn’t sure exactly where I would fit in a startup, so a generalist role with ownership and a broad range of topics I could cover really intrigued me. Furthermore, I had known Maitham Dib, the founder of Vital, for 10 months prior to joining. This made the transition to joining the company a natural one for me.
What can someone expect from this role in terms of responsibilities?
The role of a CoS can vary depending on the founder and the stage of the company. In my case, I work with a solo founder and consider myself an extension of his brain, which is fulfilling. My job involves looking at Maitham’s workload and taking on tasks to free up his time for higher priority topics.
Currently, I’m focused on two main areas. First, I’m dedicated to building our outbound sales processes, making them repeatable, and creating a sales playbook that can be easily handed off to a senior sales team member. Second, I contribute to product strategy by brainstorming our next product iterations. Lastly, about 20% of my time is spent handling ad-hoc tasks that require immediate attention, from compliance to organising offsites.
Tell me more about these burning issues that require attention.
Absolutely, sometimes it feels like I’m part of a military SWAT team (laughs). For example, when a problem arises, the founder and I come together to diagnose the problem, often run an experiment, and then scale the solution. As the CoS, I am often responsible for ensuring that it is successfully implemented and enabling a smooth transition to someone else in the organisation. Overall, understanding the founder’s mindset is crucial, which translates to grasping what actions they would take in that situation and truly comprehending their thought process.
How was your transition from VC to CoS?
Honestly, it has been a great experience. Transitioning from VC to a sales-oriented company has been a perfect fit for me. In VC, a significant part of the job is similar to sales, such as prospecting deals, reaching out to founders, hustling to get an introduction, following up, and qualifying a company. The rhythm and cadence of these activities are remarkably similar to the CoS role, making the transition feel quite straightforward. Moreover, I now finally appreciate why there are so many sales tools — something I may have overlooked during my time as a VC (laughs).
What happens after doing a lot of firefighting as a CoS?
I think there is a negative connotation associated with being a CoS for a long time, as if it is not a career path. However, if you are good at it, enjoy working cross-functionally, and like working with the founder, I see no reason why this should be the case. As for me, currently, I’m really happy evolving with the needs of the company. I’ve had peers who have graduated to more of a Revenue Operations role, which I think could be interesting. Let’s see what the future holds.
What would you advise someone who is interested in becoming a CoS?
First, join a CoS community. For example, there is one called the CoS Network that regularly posts cool opportunities. I think mingling with VCs can also be helpful since they usually know well before anyone else if a startup that is “hot” would need a CoS. All in all, the title doesn’t matter as long as you gain exposure to the founders, learn about what it takes to scale a business, figure out which areas you enjoy and over-index on — it’s all valuable.
#3 Jasmin Heimann (Procuros)
In 60 seconds, how did you become a CoS at Procuros?
I started my career in tech as a VC for a couple of years, working closely with B2B founders and getting to know their businesses. After a while, it became clear to me that I really wanted to be a part of the story and experience the ups and downs of an early-stage startup myself. This is how I ended up at Procuros, starting out as a venture development manager, and then organically growing into the CoS role.
What can someone expect to work on as the CoS?
There is no clear definition of what a CoS role looks like or what it should entail. To describe it, I like to use an analogy from sports: the founders decide on a game and the playing field, and I make sure that the players are best equipped with the information, tools, and processes to be able to win and play together effectively.
I also see myself as an honest sparring partner to the founders, ensuring smooth bottom-up and top-down communication across the company. In more practical terms, it means that you will ensure that things get done.
What are the key characteristics of a great CoS?
I believe a great CoS should be excellent and quick at context switching, moving from strategic-level discussions to nitty-gritty operational tasks. For example, they should be able to work on website copy one moment and then engage in a deep conversation about where the company should focus in the next 6–12 months. Also, due to the complexity of building a startup, the ability to simplify things and break them down into more digestible pieces is really helpful. Last but not least, having a low ego is crucial. This translates into taking on any job that contributes to the success of the company to some degree. In short, the main purpose of my role, in my opinion, is to do whatever it takes to put out fires and bring the company one step closer to success.
What comes after the CoS role?
It’s a good question (laughs) that I often ask myself. Apparently, many CoSs start as generalists and then find their zone of genius after gaining more exposure across different areas of the organisation. I see a couple of different routes to take as a career path as a CoS: one is to double down on one area, such as leading expansion into new markets, or to stay as a CoS until the company has reached a certain level, and then jump ship to become a CoS at another startup if you prefer a certain stage — or to remain a CoS and experience the company’s growth through different stages.
#4 Jonas Morgner (TradeLink)
In 60 seconds, how did you become a CoS?
Looking back, it feels less like a strategic career move and more like a natural evolution. I initially started as a Founder’s Associate and worked on tasks related to the priorities of our founders. As the company grew, so did my role. It wasn’t about doing more, but rather stepping back, understanding the big picture, and finding ways to add strategic value. It felt like the path most in tune with my interests and strengths, and I chose to embark on the wider, less-trodden path. Today, it was the right decision.
What are the main differences between the Founder Associate and the CoS?
Many see it as sequential roles, but in my opinion, the CoS role does not necessarily have to be the next level of the Founder Associate position, although there may be some overlap between the two. The CoS role is better suited for a more complex company, with the main goal of aligning different teams and stakeholders. In contrast, a Founder Associate is likely more focused on getting things done and increasing the founder’s bandwidth. In our case, we created this role after our organisational complexity increased as a result of the Series A.
What are the things you should consider before becoming a CoS?
The main decision is whether you want to go broad or deep. As a CoS, you will touch on a broad range of topics and rarely become an expert in any one thing. Personally, I am intrinsically interested in how to build a company, and this is the perfect role to learn that. For example, as a CoS, you see decisions come to life and the reasoning behind them, which puts you in a prime position later in your career as a potential founder yourself.
What are the main misconceptions about the CoS role?
It’s funny that you asked that. In the past, I’ve talked to people who expressed a strong interest in a CoS role and desire to learn about building a company but didn’t want to be involved in hiring or culture. This is a misconception. In my perspective, the CoS role involves a lot of building culture and recruiting a team. You might not be interviewing candidates, but you will influence how to build an effective culture. The second misconception can be that you work on strategic topics all day. In reality, more often than not, you are running operational initiatives between teams that nobody else has the capacity or clear mandate for.
What are some of the challenges from the CoS role?
As you help grow the organisation and see the team increase in size, you will likely still not officially be part of any one team or cadence. Therefore, the work can sometimes feel isolated. This goes along with the fact that this new “in vogue” role can be misunderstood, and newcomers might not really understand what you do or the value you bring. Last but not least, you often jump to different projects after a few months, which generally means you won’t have a long-term mandate. For one reason or another, this can be hard for someone after a long time in this role. But keeping this in mind, this role can give you so much energy and fulfilment.
Thank you all for the great insights, and best of luck moving forward.
Last words
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About the author
This piece is written by Michelangelo Pagliara, co-founder of Operators & Friends, ex-FA at Strise, and ex-VC Analyst at Antler, Samsung NEXT and KPN Ventures.
