Hiring your Chief of Staff too early?

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Luke Shipley
March 10, 2023
Updated on:

A Chief of Staff is an essential asset in any organisational structure, providing the much-needed connection between all business areas. This role interacts with all levels of the organisation offering their unique insight and expertise in understanding organisational dynamics while collaborating with departments and team members. 

As such, this role acts as a critical resource for a CEO in obtaining the information needed to make well-informed decisions to affect the entire organisation positively. By fulfilling this function, a Chief of Staff puts their unique stamp on an organisation’s trajectory by helping shape its future direction. 

Armed with this knowledge, they contribute to conversations with the CEO, thereby assisting them in making decisions that have far-reaching consequences across the company.

Timing is extremely important when making critical hires for a startup, as they help establish the foundations needed to support the company’s growth. At Zinc, we felt that adding a Chief of Staff at number 9 (versus the average of 26) was integral. 

By making this hire early on, we were able to prepare for and implement essential management systems, performance metrics, and KPI processes that would have been even more difficult if done during later stages of expansion. Having these key pieces in place helped us ensure our growth wouldn’t outpace our capacity to accommodate it.

Benefits of hiring a Chief of Staff early

When it comes to creating a startup headcount plan, early hiring of a Chief of Staff has a variety of benefits. A Chief of Staff helps the senior management team create and maintain management structures, which sets the business up for success. The early introduction of KPI processes (we follow an OKR structure) increases visibility and accountability while discouraging operational and people debt. 

With improved communication and alignment within the business, bottlenecks are avoided, allowing business plans to be more effectively implemented. An executive-level hire fills any management gaps or supports particular areas where the leadership needs more expertise. Properly leveraging a Chief of Staff allows companies to scale up quickly and efficiently.

On average, a Chief of Staff is hired at number 26 in startups. Less than 50% of Series A startups have someone in this role. We made this hire as employee number 12, here’s why…

Data from Linkedin on the average employee number a Chief of Staff was hired into B2B API & Saas startups.

The role of a Chief of Staff is critical to the success of any company. An effective Chief of Staff must possess many skills, qualities, and experiences that set them up for success. Here are some characteristics that define an effective Chief of Staff:

Key characteristics of a successful Chief of Staff

1. Broad problem solver–A CoS should think critically and solve complex problems from multiple angles. They should quickly assess the situation at hand and propose solutions that address both immediate and long-term needs.

2. Good people person–A successful CoS should be a strong people person with excellent interpersonal communication skills, as well as the ability to establish strong relationships with colleagues and peers. They must also effectively manage their team’s performance by motivating, developing, and coaching them to ensure they reach their potential.

3. Strong communication & listening skills–An efficient Chief of Staff should possess exceptional communication skills and have a keen ear to listen closely to what others have to say to get accurate information quickly. By being great listeners, they gain valuable insight into an array of internal issues, which allows them to make better decisions on behalf of the teams’ best interests.

4. Technical understanding and data literacy - if you’re going to transform organizational efficiency it can’t be all people based. You’re going to need to excel at excel and be able to plum different systems together better than the average salesperson. 

When developing the role of Chief of Staff, consider the above development plan that outlines the roles and responsibilities for their first 18 months. 

Considerations before hiring a Chief of Staff for your startup

Making an early hire for this role is an important decision for any startup, as it has a dramatic effect on the company’s growth and scalability. Before making such a hire, there are several factors to consider.

Size and structure of the startup: The size and structure of the business should be taken into account when considering whether or not to hire a Chief of Staff. Generally, the larger and more complex the organisation, the more likely it is that having a dedicated CoS helps streamline processes across teams and departments. 

It’s also important to look at how roles within the company are currently distributed; if there isn’t clarity on who should manage what tasks or if everyone is wearing multiple hats, a Chief of Staff to align everyone could be beneficial.

The mix of levels within the organisation: Another factor to consider when deciding whether or not to bring on a Chief of Staff is how many levels exist in your organisation. If there are too few levels between employees and leadership (e.g. only one intermediate level between employees and executives), bringing in someone with more experience could help fill that gap in management and create opportunities for development for employees.

The type of Chief of staff you’d like to meet: this starts with the type of organisation you are. Are you a meeting-heavy people organisatioin or are you heavily remote and async. The former requires more meeting shepherding skills the latter requires excellent writing ability. If you’re a technical organization, with a technical product, leaning into someone technical is wise.

The transition from a small team to a larger one:
A key benefit of hiring someone for this role early on is they help effectively manage the transition from a small team to something larger. This includes helping lead people through changes, developing new processes and systems, creating ways for members to collaborate effectively, and staying up-to-date with industry trends so that decisions remain informed by the latest developments within their field.

Impact of a Chief of Staff on the startup's growth and scalability: Ultimately, having an experienced Chief of Staff could provide considerable value when it comes to scaling up quickly with minimal operational debt or people debt incurred along the way. They improve communication between departments which helps ensure everyone remains focused on long-term goals.

Challenges with hiring for roles too early

When making an early-stage Chief of Staff hire, there are several potential challenges startups should be aware of.

One common challenge is defining the job description and finding the right candidate. This is especially difficult given the fluid nature of a startup, where roles and responsibilities may shift quite rapidly. To minimise hiring mistakes, it’s important to consider not only the skills and experience needed for the role but also the qualities that would make someone successful in such a complex environment.

  • With the unique demands of taking on a Chief of Staff role in an early-stage startup, finding a qualified candidate may prove difficult. This is because most experienced professionals in this line of work tend to seek out later-stage businesses with more structure and less risk. Therefore, the challenge lies in finding someone who has the qualifications and capability to implement effective adjustments without bypassing the well-honed processes which come with working in mature organizations.
  • Or in cases where they don't, finding someone who knows how to get stuff done quickly and effectively  The right candidate will have a deep understanding of business, and come equipped with both strategic thinking and tactical execution to make sure they are aligning the team's vision with reality.
  • Startups must keep in mind that they’ll need someone in place who is both flexible and adaptable; this is particularly true when it comes to Chief of Staff roles, as such positions require individuals who are comfortable pivoting between various operational tasks or projects depending on what is requested or needed at any given time.

Ultimately, while making an early CoS hire presents its own set of challenges for startups, doing so provides tremendous value over time by helping ensure processes and systems remain efficient, organised, and effective—all of which aid in achieving sustainable growth and scalability moving forward.


Whether you’re outlining your startup headcount plan, looking to make your first talent hire, or hiring your first chief of staff, timing is essential.

Adding a Chief of Staff to a startup can be extremely beneficial in driving growth and scalability. From helping define global objectives, developing strategies for achieving them, and maintaining efficient processes and systems, the Chief of Staff offers tremendous value in aiding startups on their journey toward sustainability.

If you have a hierarchical startup from the offset, perhaps making this hire early isn’t necessary. 

That said, several unique challenges come with making an early hire of a Chief of Staff; these include defining the role and finding the right candidate, managing costs and budget constraints, and ensuring that the individual is flexible and adaptable.

When considering an early hire for a Chief of Staff position at their startup, founders should consider their specific needs and circumstances to maximise the chances for success. By doing this—and by taking full advantage of the role’s many benefits—startups create a solid foundation from which they launch toward sustainable growth and sustained success.

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