Why a Chief of Staff for Your Startup Is So Important

Startup founders and practitioners are often debating the best actions to take and decisions to make in their early stage companies. Determining the right hires has often been a major part of this converstaion. While some startup leaders are busy debating the need for Human Resources early in an organization, deciding if an analytical marketer or a creative marketer is the best first hire, and choosing the right time to bring on an Executive Assistant or EA to optimize their own lives, the hot topic on the table lately has been around hiring the role of Chief of Staff. There is a growing conversation around if startup leaders and founders should hire a Chief of Staff or COS and here at Visible we believe it is one of the most important hires you can make. 

A Chief of Staff is so important for your startup because their role is designed to be an extension of the c-suite’s leadership and strategy. Their role is an important one as it will allow companies to scale faster and more strategically. Between the Board of Directors, Executive Board, Stakeholders, and employees, startups have a lot of moving parts and a Chief of Staff can be the cog in the machine that makes all those pieces work smoothly together. 

A Chief of Staff is the right-hand person to an executive team member, typically the CEO or COO. The COS is tasked with managing the executive’s goals, priorities, internal and external operational tasks, and special strategic projects as needed. A more familiar right-hand person to a c-suite executive is the Executive Assistant. An Executive Assistant manages the day-to-day schedule and obligations of an executive, ensuring said executive has the ability to get to all their priorities for the day and is maximizing their time for the best possible use. As an Executive Assistant, a Chief of Staff is also working directly with an executive. But unlike an Executive Assistant, the COS is not responsible for optimizing the time and day of that executive, rather helping to optimize the strategic initiatives occurring across the company that the executive is driving. EAs tend to spearhead administrative strategy to optimize an executive’s output, while Chief of Staff’s spearhead strategic strategy providing input and ensuring the executive’s output in a different way. 

The typical responsibilities included in a Chief of Staff role may include:

• Managing Executive Goals and Priorities 

• • • While an EA is always looking to optimize their executive’s time, a Chief of Staff helps determine what optimized time really looks like. For CEO’s and COOs, there is plenty of work that could easily fill the day. But what work is most important for business development, moving the business forward? A Chief of Staff helps direct the decision making and serve as a sounding board for the CEO, owning the task of keeping the executive aligned to the goals he or she set forth to push the business forward. 
    • A COS considers these executive goals, and even formalizes them in a framework such as the OKR framework, or Objective Key Results framework. With these executive OKRs formalized, a COS helps guide the CEO/COO’s priorities day over day. 

• Operational Tasks 

• • • With specific areas of work, including Board Meetings and other critical decision-making sessions or meetings on the agenda, the Chief of Staff helps manage these priorities by handling operations tasks like agenda setting and distribution, communications with teams across the startup to gather insight and updates on various company-wide priorities and progression. 
    • Not only will a Chief of Staff work on internal operational tasks like meeting prep and gathering updates and tracking company progress towards goals, they also tend to handle external operational tasks as well. These external operational tasks might be sending investor updates to stakeholders, serving as the point of contact to the Board of Directors representing the CEO’s office, or even working on communications and PR. 

• Special Strategic Projects 

• • Startups move fast and different priorities and special obligations come up for leadership out of the blue. Additionally, as your startup goes through strategic growth periods like fundraising or even down the line acquiring smaller startups, the priorities of a CEO’s time will greatly change. These strategic times are the perfect way to utilize a COS. If fundraising is going to take up a significant chunk of a CEO’s time, a Chief of Staff can step in and manage aspects of that strategic task such as deck assembly, overview materials for the potential investors, and communication with parts of the business that need to deliver information for said fundraising presentation. 
  • Chief of Staff’s are typically very versatile in their skill set with communication, strategic thinking, and analytical skill sets. This background makes them the perfect person to take on roles that require a strategic thought and concise summary but are potentially too time constraining for a CEO to dedicate all of their energy to. 

With their unique mix of hard and soft skills, executive insight, and strategic position in the company, a COS is a major value-add to any startup.  Our team at Visible has identified 7 primary ways that a Chief of Staff can strengthen your startup.

They Keep You Focused on Your Priority Items 

The day in the life of a CEO or COO is extremely hectic. Serving as the final say for most aspects of the business, its easy to get caught up in each and every decision and task debating the right decision and possible outcome. However, if every decision was weighted the same by a CEO, a business would never run efficiently and would not last very long at all. A Chief of Staff helps manage your priorities so that you can hit OKR goals. Let a Chief of Staff filter out the daily decisions and direct your time to the most strategic decisions at hand, the ones that align to your OKRs and the ultimate success of the company. These priority items should be the focus of the CEO while a Chief of Staff can filter out the smaller fire drills and decision-making to keep the business running smoothly. 

They Facilitate the Smooth Flow of Information

A Chief of Staff can serve as a positive bottle-neck for updates about the business. By allowing all updates to flow in to the COS, a more organized and contextualized executive summary of information can be produced. With weekly sales updates, customer success updates, marketing updates, product updates etc… going directly to the COS, the COS can then distill down the most important points for the CEO so that priorities are focused on and all the right information gets where it needs to go. A COS can also help with information from the CEO to the correct parties by helping plan out executive communication calendars and processes so that everyone at the company feels heard and leadership can be more transparent. 

They Inform Your Strategy and Decision-Making

A Chief of Staff is a great resource as an executive to stay connected to the various happenings across departments. A COS can inform strategy and decision making at the executive level by serving as the point person for all updates across the company. With the COS providing an executive summary level view of company happenings, strategy and decision-making can happen much quicker but with all the information still informing said decision-making. 

They Maximize Your Time While You Scale

A Chief of Staff can be a major time saver in the c-suite. By having a COS prioritize your tasks and focus points, time will be maximized to tackle deep-think projects vs. quick fires that ultimately aren’t deal breakers for the business. As priorities shift while the business grows and the needs shift, the time an executive is spending on tasks can stay with the priorities as opposed to always adding on to the plate. 

They Tackle Special Projects 

Special, yet crucial, projects come up as companies scale. Maybe it’s a fundraising round or a special product release or announcement or a presentation at an upcoming industry topic. Whatever the case, the COS position is the perfect position to spear-head special projects alongside the CEO. By letting the COS spearhead things like building investor decks or drafting V.1 materials for a conference presentation,  leadership to keep focusing on daily priorities and jump into special projects when their input is needed or for the final pass. A COS is a headcount that is ready and onboarded to flex their time to the most pressing need at hand. 

They Provide Oversight and a Fresh Perspective 

Startups are a grind. As much as a founder or executive team may have a lot of experience, they are working within an echo-chamber at times as the startup scales. Bringing on a Chief of Staff, especially one with experience from other startups, can bring a fresh viewpoint into the c-suite to advise and serve as a sounding board moving forward. 

They Push Your Business Forward 

Ultimately, a COS can be a strategic player in moving the business forward at a faster pace. They streamline and prioritize for the CEO, serve as a great resource for special strategic projects, and serve as a vital point of external and internal operational communication. Tasks that, when done right, take a good startup to great and great startups to unicorns.

Knowing the value-add a COS can have to a business, when is it the right time in a startup journey to hire one? It really depends on where your business is at. Perhaps your startup is at a critical juncture and needs to scale 2x as fast in the next 12 months to come out on top. This would be a great time to bring on a COS to maximize the CEOs time in this critical period of growth and business development.

On the flip side, maybe your startup just closed a large round and valuation has doubled. Now there is more expectation than ever to perform and exceed growth targets, a great time for a Chief of Staff to step in and help prioritize and provide a fresh perspective at the executive level. Maybe there is a Sr. leader on your team that you’re afraid may leave the company if their specific function doesn’t have any leadership headcount opening up. Bringing that person in as a Chief of Staff can help them scale their leadership potential and help your startup maintain a top talent in the org, potentially a future executive leader down the line. Whatever the reason, when you find your startup strained at a growth point, it’s always a good idea to bring on a COS as soon as possible. 

Once you’ve decided to hire a Chief of Staff, it’s critical to equip them for success at your startup. This process starts even before a COS hire is made. When you’re putting together the job description for your Chief, be sure to fully scope out the role. Reserving them for “special projects” alone is too ambiguous and may lead to the wrong person being hired or worse that role not being fully maximized to its potential. 

Scope the Role

• Take a look at peers or aspirational companies in your space, dig into how they have positioned their Chief of Staff role. Read the job description and work with your talent team to clearly outline the tasks (even if they are ambiguous to start) as best you can and articulate the hard and soft skills that are needed to work well with your executive team. 

Find a Great Candidate

• Never fill the Chief of Staff role to check a box or because of a time crunch around a specific growth project. The right candidate is out there, but patience may be needed. Work with your personal network to crowdsource strong COS candidates. Talk to the leadership team at your org to understand if there are any good internal candidates for the role. With a clear scope of the role, a great candidate will be found but its critical not to settle for someone that doesn’t check the boxes of the role that you scoped. Consider sharing the JD for your COS in new networking groups and industry groups that have been previously untapped by your recruitment team. 

Manage your COS 

• Just like your Board of Directors and any other new employee at your org, ensure a clear onboarding plan is in place before your COS starts. With this role, more than many others, clear goals and KPIs for success should be laid out right away. A 30, 60, 90 day expectation is a great way to make sure your COS is on track and is an efficient way to use to guide your management of their role, especially if the job is flexible in task. If the KPIs are clear, the day to day can change as special needs arise but it will be clear to you and the COS what the expectation and measure of success truly is. 

Scaling your startup is a challenging feat. With startup founders juggling so much every single day, the Visible team truly believes a Chief of Staff is a major value-add to any startup with major growth aspirations. All in all, they are a strategic partner and resource to your business that can help with special projects, streamline internal and external operational communications, and help keep the business priorities clear and on-track. 

For more information about how Visible helps Chiefs of Staff streamline their executive and investor communications, learn more here.