The Chief of Staff Role at Upflow
Jun 28, 2023
Right after Upflow’s Series A, Alex, co-founder & CEO, decided to initiate the hiring of a Chief of Staff. Back then, he had already spent the time to clarify the need and scope of the role. The team was about to grow from 15 to 50+ people, along with the increasing complexity of the organization. He envisioned the need for someone to work alongside him. In this context, I joined the team as Chief of Staff to the CEO in January 2022.
The Chief of Staff role takes very different forms depending on the organization. The responsibilities of a Chief of Staff in a 5,000-people corporation are very different from those in a 50-people startup or in public administration. However, there are some common characteristics.
Over the past 18 months, I have had numerous internal discussions with colleagues and external discussions with peers and CEOs on the Chief of Staff’s role and how it translates here at Upflow. The goal of this post is to structure and share those insights, hoping it can serve as a point of reference for similar organizations.
Why, the Chief of Staff’s raison d’être
Why might an organization need a Chief of Staff?
In an ideal world and once the company reaches product-market-fit, the CEO focuses their time on four top priorities: (A) creating and implementing a strategy to achieve the company’s mission and reach its vision, (B) building and enabling a top team to execute this strategy, (C) driving culture change as the organization grows, and (D) financing it all.
But they often end up spending a lot of time on (E) running everywhere and spending time on operations. CEOs can feel overwhelmed and overexposed. They are frequently preoccupied with the organization's productivity, the inefficient flow of information slowing down decision-making, the endless back-and-forth and follow-ups, and experience difficulties giving up on things they used to do - from sales to ordering coffee. Being a CEO is exhausting. It is often challenging for them to find time to focus on their core duties. Yet, they do not need to intervene in every topic brought to their attention actively.
That’s where the Chief of Staff comes in, acting as an extension of the CEO to maximize their impact, help them make decisions, and reduce the pressure on them.
Note that you probably don’t need a Chief of Staff before the company reaches product-market-fit, or at least not one with the scope I describe in this article.
Panorama of the role
In a very insightful study published in February 2023, Roland Berger drew a panorama of the Chief of Staff role in the US and in France - the two geographies where Upflow has permanent offices in. We learn that:
There are 6 times more Chiefs of Staff in the US (4,700) than in France (800).
The US Chiefs of Staff tend to be much more experienced than their French counterparts. 90% of them are 40+ years old, while 80% of French Chiefs of Staff are under 40 years old.
Females are more represented in the French Chief of Staff population (45%) than in the US (30%).
Most Chiefs of Staff have a cross-functional background. 25% come from Consulting & Finance, 25% from Sales & Business Development, 15% from Operations, 15% from Administration, and 15% from other functions.
Most US Chiefs of Staff work in large organizations (75% of them have 1,000+ colleagues), primarily in public administrations (only 30% work in private companies).
Most big French companies already have a Chief of Staff (70% of the CAC & Next 40, and 40% of the SBF & Next 120).
In a nutshell, the Chief of Staff role is well-embedded in the US. They are more experienced, mostly male, and work for large corporations, particularly public administrations. In France, most big companies have a Chief of Staff, who is generally younger and equally represented by both genders. Candidates mostly come from strategy and cross-functional roles.
Missions at Upflow
Now, with this panorama and skillset in mind, here are the missions of Upflow's Chief of Staff. They describe their focus while the company grew from 15 people to 50+ people post-Series A, covering an 18-month period. I illustrate each item with an example of an actual project.
The scope of the role regularly evolves as the company grows, as I will describe toward the end of this article. For context, it often starts as an individual contributor role with no direct reporting line. As the organization develops, the Chief of Staff may build an independent CEO Office composed of an executive assistant and a few strategic project managers.
The Chief of Staff's role at Upflow is organized around three main themes:
Strategic planning and special projects — Ensuring the company's mission and priorities translate into actions, and owning the delivery of ad-hoc and strategic cross-functional initiatives.
Rhythmics and communication — Accelerating decision-making with the appropriate rhythm and information flows, and keeping our external stakeholders engaged.
Sparring partnership and facilitation — Supporting the CEO's thinking process and acting as the "first door" before their door.
A. Strategic planning & Special projects
One of the Chief of Staff's missions is to prevent a lack of strategic alignment across the organization and to act as the CEO's extension in navigating cross-functional initiatives.
1 — Make the strategy operational, coordinating strategic planning
When he joined Upflow, the team was running on a simple version of the OKR methodology driven by the CEO. One of the Chief of Staff projects has been to strengthen our OKR implementation and onboard all the departments. You may find more on this project in this blog post.
“As we have been scaling our use of the OKR methodology at Modjo, we have realized the critical importance of starting with and consolidating the basics. This entails not only having a clear mission (what we are trying to achieve) and a compelling vision (what the world looks like when we succeed) but also developing a strategy — a plan to win that describes how we will achieve our vision. Only then will your OKRs be meaningful and create commitment among the team. To set things in the right direction, begin with the bigger picture and then cascade actions accordingly. To accomplish this, I am facilitating workshops and consultations with the company founders, the leadership team, and the entire team to generate ideas and leverage collective intelligence. The objective is to define the best strategy that would enable us to achieve our ambition of becoming a European leader.”
2 — Streamline strategic & cross-functional initiatives, performing research and formulating actionable recommendations to the CEO
For instance, the Chief of Staff wrote a plan to refresh our values and collectively discover and define our operating principles. The goal of this project was to document core tenets describing the way we work and are together, the specific behaviors and skills we care about most. This would help us hire for cultural fit, onboard and review people's performance, and make decisions day-to-day. He organized a series of workshops and was both accountable and responsible for the execution of this project. You can learn more about our operating principles on our careers page.
A second example: The Chief of Staff worked on scoping and documenting a Talent/People senior hire. He interviewed several peers and HR leaders in the ecosystem to understand the missions of a VP Talent/People, when companies usually make such a hire, what the expected key competencies are, and where this person would sit in the organizational chart. Then, based on this research, he sent a recommendation to the CEO.
And a third example: The Chief of Staff wrote a plan for Upflow to make a corporate Environmental, Social, and Governance (ESG) commitment and take action. While helping B2B businesses get paid, improve their cash flows, and the overall health of their business, Upflow wants to be a positive force on society and the environment. Upflow wants the world to be slightly better with us than without us and understands it is beneficial for its organization and business to build long-term resilience to environmental, social, and governance challenges. The Chief of Staff interviewed several ESG leaders and built a believable plan on how to start our ESG policy - in small batches yet meaningfully, as per our operating principles.
“My team and I handled the integration of Pulp, a startup specialized in table payments and click & collect. This involved working on internal communication to reassure the teams and external communication to engage prospects, clients, and partners around this new vision. It was also necessary to establish working groups focusing on HR, Operations, Finance, Sales, and Product to create synergies between the two companies and maintain Pulp's growth momentum. I also worked on other significant projects, such as implementing a stock options program and renaming the Spanish subsidiary.”
B. Rhythmics & Communication
Another part of the Chief of Staff's mission is to avoid ineffective communication, both internally and externally, limited transparency leading to lower team engagement, and hindered decision-making.
3 — Monitor the progress toward our goals and implement transparency
The Chief of Staff worked on reinforcing the internal transparency on our performance by refreshing the reporting available company-wide. This project has been performed hand-in-hand with our Data team.
4 — Take the temperature upstream from the frontline to understand which communications are needed
As the company grows, the meetings embedded in our operating systems become obsolete, and we need to reinvent them so they always support a clear purpose. The Chief of Staff reviewed our internal rhythmics to best match our current needs (all-hands, standup, retrospectives...). This is an effort that shall be made regularly.
“When scaling, three critical elements tend to falter: internal communication, knowledge sharing, and decision-making. To address the first one, I have implemented a structured internal communication system with established routines and rules to foster context-sharing throughout the entire organization. Our week kicks off on Monday morning with a dedicated Kick Off session, while every Thursday, we gather for a Town Hall meeting, where we not only celebrate newcomers but also provide a platform for Spendeskaries and Spendeskers to share valuable insights about their work. Additionally, we regularly organize company Q&A sessions. As our team has grown to a size of 600 Spendeskers, I recognized the need for a dedicated individual to lead our internal communication efforts, which has now become a full-time role.”
5 — Align the organization with the C-level vision, connecting vision & execution, and ensuring information flows up/downstream
The more we onboarded new joiners, the more challenging it was to ensure that everyone was personally connected to the company's vision, mission, and strategy. That’s why the Chief of Staff took time to discuss 1:1 with everyone to support the collective understanding of our strategy and source feedback and concerns. This feedback would then inspire the messages shared during the company's quarterly all-hands meetings.
"One of the most important things in an organization is how well people collaborate and work together as a team. But sometimes, misunderstandings or conflicts can happen. As a Chief of Staff, you play a critical role in handling these issues. Your job isn't to judge; it's to help make things smoother. We believe that most conflicts in the organization happen because people lack information. So, your key skill is to listen, understand, and support everyone involved in finding a solution. This means being a good listener, knowing how to negotiate and get people to think logically instead of emotionally, being creative, having good communication skills, and really knowing what the organization values and wants to achieve.”
6 — Oversee top management and company-wide meetings and communication
When the Chief of Staff role was created, post-Series A, the company was currently hiring and onboarding an experienced leadership team to drive Upflow to its next stage. We thus needed some rituals to work as a unit. The Chief of Staff worked on introducing and delivering regular leadership meetings to improve coordination and alignment.
As another example, the Chief of Staff organized some offsites with the leadership team. The purpose of those days is to bring this team together. To balance productive and casual moments, we open a transparent forum to discuss the challenges ahead of us and reflect on our priorities and how to better operate as a unit.
7 — Accelerate decision-making by acting as a proxy for the CEO in meetings
The CEO doesn't need to be in all meetings. For instance, we had at some point an internal discussion about how we should define and report on the opportunities we generated from our partners. This required some alignment between our Alliances and Business Operations teams. The Chief of Staff represents the CEO in some of those meetings to ensure we move forward fast.
Another example; on several occasions, the CEO wanted to consult several stakeholders internally before making a decision. Instead of him spending three hours interviewing five people, the Chief of Staff did the heavy lifting here, running those interviews, compiling key learnings, and formulating a recommendation to the CEO to accelerate decision-making.
8 — Manage & prepare communication with external stakeholders
At Upflow, the Chief of Staff attends the quarterly Board meetings as an observer and is in charge of preparing the session. Upon onboarding, he refreshed the deck template, sourcing best practices from Silicon Valley's investors. He is responsible for compiling all important information, translating it meaningfully, and ensuring that the meeting's working session is fruitful.
9 — Act as an external ambassador of the CEO, supporting them in stepping up as an opinion leader
Upflow’s vision is that B2B payments should be as easy as B2C. Realizing that late payments are a technology problem, not a bad payer problem, its mission is to revolutionize how B2B companies get paid. The company's strategy to achieve its mission is to start with a SaaS platform for business teams providing analytics and collection workflows before solving this problem through payment and financing. The CEO is Upflow’s face externally, and it is part of his scope to act as a thought leader in the finance space, promoting Upflow at the same time. The Chief of Staff supports him in this duty by reaching out to partners, press or podcast hosts, and chasing high visibility placements. For instance, he helped the CEO attend CFO Connect 2022. He also pushed a CEO’s thought leadership article to a popular media in the European startup ecosystem, Follow Tribes.
C. Sparring partner & facilitator
The last main area of intervention of the Chief of Staff at Upflow is to challenge and strengthen the CEO's convictions and ensure their stakeholders' interfaces make the best use of their time.
10 — Act as a mirror, actively listening and feeding the CEO’s thinking process by challenging their proposals and conclusions
The Chief of Staff meets the CEO every week and leverages every opportunity to brainstorm together on the current company priorities and challenges. Of course, the CEO is not alone and closely relies on his relationship with his co-founder to make the best decisions for the company. The Chief of Staff builds on those founders' discussions, shares a more external point of view, and engages in a coaching-type/active listening and discovery discussions to strengthen the CEO's intuitions and inner convictions.
I recall here that, in Upflow’s context, the Chief of Staff does not have decision-making power in any areas of the business or product. Their role is to support, inform, challenge, and generally strengthen the decision-making process of the leadership team and especially the CEO, but he is not responsible for actually arbitrating cases.
Angélique de Taddeo began her adventure with AB Tasty years ago when they were a team of 25 (vs. 300 in 2023). She has grown alongside the organization, progressing to the position of Chief of Staff after fulfilling multiple roles within the company, and now regularly acts as advisor/coach to their CEOs.
"As I joined AB Tasty in its early days, I've had the incredible opportunity to delve deep into its history, culture, and the minds of our CEOs. As the company grows, pleasing everyone becomes harder, and making effective communication vital. I rely on informal chats with employees for valuable insights, guiding our CEOs with top-notch advice. A few years back, I introduced the concept of Stay Interviews within AB Tasty. It's a nifty concept that's gaining traction in the US but is less famous in France for now. Stay Interviews reveal what keeps our team members engaged and areas to focus on. And here's the kicker: the discussions I have with our CEOs, where I spill the beans on all the feedback from the field, play a vital role not only in improving their internal communication but also in making the best decisions. It's all about making sure they address the burning questions employees have on their minds. By keeping the conversation flowing, we create a more cohesive and connected work environment.”
11 — Advise the CEO on their agenda, prepare meeting notes, and interface with stakeholders
In the absence of an Executive Assistant, the Chief of Staff audits the CEO's agenda every 6 months to ensure that his time is well organized and that he can make time to focus on his top priorities.
Another example. The CEO spent several months in our US office. The Chief of Staff supported the CEO in preparing his stay ahead of time and fully leveraging his presence there, both by spending meaningful face time with the team and by meeting local partners and stakeholders.
12 — Filter requests to save time for the CEO
In a relatively small company, filtering requests to the CEO can be slippery. You don't want to add unnecessary friction to the relationship between the leadership and the CEO, but instead, ensure that the communication is smooth and efficient. The Chief of Staff supports the leadership team in living and communicating by our operating principles when interfacing with the CEO. He can act here as the first door before the CEO's door, ensuring cases are well-documented, and that the CEO will have everything he needs to decide when the conversation will start.
Not filling the gaps
Without going through the long list of things the Chief of Staff at Upflow does not do, I want to flag one specific element of the role that may differ from one company to another and have a profound impact on the Chief of Staff’s day-to-day.
When discussing with some of my Chief of Staff peers, I realize that some of us are expected to temporarily fill gaps in the organization, while some are not.
At Upflow, I do not fill the gaps. We often say that I am expected to build houses, but not to live in them. For instance, I drew a battle plan to get started on our ESG policy, but won't be the one responsible for it as it unfolds. As another example, I built our 360 review process, but it is our People team's responsibility to run it. I help the CEO anticipate fires, for instance, changes in the team, instead of acting as a smoke jumper. I do not act as a leader in the interim and do not own a specific area of the business or product.
This is not how all organizations work. This can be driven by the appetite of the Chief of Staff. In my case, I don't feel capable enough in Sales to successfully lead the Sales team while our VP of Sales is on parental leave, and neither do I feel capable enough to lead our People efforts if we temporarily have no one in charge. So I prefer not to commit to this. If our VP of Sales is to be off for a few months, my role as Chief of Staff is to have anticipated that ahead of time and built a contingency plan together with the Sales and People leaders so the organization and business continue to run as usual.
The above missions describe the Chief of Staff's first 18 months in the role, growing the company from 15 to 50+ people post Series A. As the company keeps on growing, the role of the Chief of Staff will too. Here are some options and areas we may reinforce in discussion with the CEO:
Give more independence to the Chief of Staff and get him to represent the founders internally on more occasions.
Act as a real coach to the CEO to help him become a "10x professional.”
Regularly make recommendations on our corporate strategy, including competitive positioning and financing.
Act as the first line of communication with our existing investors, before the CEO.
Onboard an Associate and build up a structured Founders Office.
This will all depend on the growth path of the organization. That's another thing the Chief of Staff needs to be comfortable with: navigating ambiguity and uncertainty.
How to be successful
Given the broad array of projects in which the Chief of Staff is involved and the variety of stakeholders they have, a few core skills appear to be key to success.
Project management — Proving a sound personal organization is crucial to face and manage many different topics simultaneously. The Chief of Staff needs discipline, attention to detail, and patience & tenacity to follow up with their stakeholders to ensure projects are delivered right and on schedule.
Business savvy — Especially in a relatively small company, understanding the market, product, and technology, and what is required for sustained operating results is very important so the Chief of Staff formulates meaningful strategic recommendations to the leadership.
Ability to see what pressures the leader faces — When referring to the professional relationship between the CEO and their Chief of Staff, we sometimes talk about a "professional couple." To make it work, the Chief of Staff needs empathy. They will need to precisely connect to their leader's pressures and find ways to lessen them.
Communication — Being a good communicator will prove to be a very useful asset in the Chief of Staff job. Personally, they are interacting with multiple stakeholders and need to be able to speak their mind with clarity. And in their relationship with the leader, they will be involved in refining their messages and ensuring that they are understood by the audience, whether internal or external.
“Focus on candidates with really strong communication and relationship-building skills. The ability to become a subject matter expert quickly is also very important, as are leadership skills, empathy, and a business-first mindset. Finally, make sure you’re bringing candidates into the pipeline that are comfortable with uncertainty, as things in this role are always going to change.”
Besides those core skills, you will need to gain your colleagues’ trust to be successful. Even though the Chief of Staff role often starts as an individual contributor role, your job is, by design, highly collaborative. You will have to build strong professional bonds with the people you will interact with and serve day-to-day.
The first thing you will want is to ensure that people understand your role and on which occasions you may work together. To do so, some explicit top-down sponsorship and communication from the CEO are always welcome. But do not stop here. Teach the role internally. You may organize a training or team meeting on the role, publish an internal “How to work with me” note, write a blog post, invite a few Chief of Staff peers, and organize a panel for your team in your offices on a Thursday night… Be creative, and show pedagogy.
Then, once the group understands how you may interact together day-to-day, prove your value. In my experience, experiencing is believing here. Go help them. Roll up your sleeves, take over a project, and make their lives easier. They will observe you can have meaningful conversations with them and even support them in their role. Trust will follow.
Why become Chief of Staff
You now have a better understanding of what working as a Chief of Staff in a Series A company may entail. To many, this role appears as an excellent career accelerator. Here are a few opportunities you may seize by moving to such a position.
Be in the CEO's head — If you are considering starting your own company at some point in your life, the Chief of Staff role can provide you with a deep and personal understanding of the CEO's mindset. This will depend on the relationship you have with the CEO and how much they are willing to open up to you with vulnerability. Being their professional confidant is a unique chance to relate to their experiences as an entrepreneur and assess whether you want to pursue a similar path.
Comprehensive understanding of how the organization functions — As a Chief of Staff, you will work closely with the company's CEO or founder and gain exposure to various business areas. You will be involved in projects with multiple teams, allowing you to develop a holistic understanding of the organization's internal workings.
Refine your strategic thinking skills — You will actively participate in high-level decision-making and strategy discussions, and you may even have the opportunity to attend board meetings. This involvement will provide valuable insight into the company's direction and vision, as well as the chance to learn from experienced leaders and hone your strategic thinking skills.
Enhance your leadership abilities — By collaborating closely with the executive team and overseeing cross-functional initiatives, you will have the opportunity to practice aligning stakeholders and influencing others. These skills will be valuable not only for your current role but also for future career prospects, whether inside or outside the organization.
The Chief of Staff's mission is to maximize the CEO's impact. For the organization, onboarding a Chief of Staff is a great way to relieve pressure from the CEO, help them find time for what matters, and support their decision-making. It proves to be a very helpful asset, especially when the company is growing rapidly.
For the person fortunate enough to secure the job, it exposes them to a wide variety of topics and strengthens their strategic thinking, communication abilities, and project management skills. To many, it is seen as a powerful career accelerator.
In many respects, this role can be a mutual success for both the organization and the individual.
I hope this post provides you with a useful example and supports your thinking. I'd love to continue the discussion - feel free to reach out.