Why Many Growing Startups Need a Chief of Staff

For startups, so much happens at once. What’s more, the CEO can’t be there for all of it. Even their best efforts to keep a handle on growth can give way to fractured processes, miscommunications, and uninformed decision-making.

That’s what Colin Bramm, CEO of Showbie, was afraid of after his Canada-based educational software raised Series A funding in 2020. “We’re pressing down on the gas pedal, [and] it feels kind of scary to not have someone who’s paying more attention to processes, coordination, and communication,” he explained after the initial celebration.

After much consideration, Bramm knew what – or, more appropriately, who – he needed to avoid these risks: a Chief of Staff.

What is a Chief of Staff?

Sometimes being a CEO of a startup can feel like whack-a-mole, where putting out daily fires often takes precedence over large ticket items such as high-level growth strategy and fiscal planning. Enter the Chief of Staff (CoS), the CEO’s right-hand person.

What are the Responsibilities of a Chief of Staff at a Startup?

Industry experts agree that the role of a CoS often varies by company, but the following functions are key to their success, especially in a startup:

• Prioritizing the CEO’s time. Fitting everything onto a CEO’s calendar can be like a game of Tetris. CoS’ know what’s important versus what can wait another week so that the boss can focus on high-level issues.
• Overseeing strategic planning and implementation. The CoS has similar, if not the same, company knowledge as the CEO, providing a huge benefit for all. This allows CoS' to answer staff questions so projects stay on task, as well as the ability to jump in when help is needed without any additional training or onboarding.
• Fostering key internal and external relationships. Now that most communication is completed electronically, it’s critical to have someone to close communication loops. This may look like sending important follow-up emails, circling back on conversations, or requesting more information on behalf of the CEO. This extra set of eyes makes it so the CEO – and the company – never has to worry about a ball being dropped.
• Improving internal processes and decision-making. A CoS has the flexibility to interact with department heads, team leads, and employees and bring that level of insight back to important conversations with the CEO. As a result, CEOs can make more informed decisions that will impact the company at large.
• Attending events to fundraise and improve outside partnerships. If CEOs could channel some Twilight Zone energy and be in two places at once, they probably would. But since that’s not a reality (yet…), the CoS is the perfect choice to step in, meet with stakeholders and potential partners, and make decisions based on how they believe the CEO would.

Sounds like a big job, right? That’s because it is. Mark Organ, CEO of Influitive, explains the complexity of the role. He says, “While the CoS makes many important decisions and has strong leadership skills, this is a service role. The job is to make me a superhero.”

In other words, the CoS is always the bridesmaid and never the bride. But even though they may not be front and center, the work of the CoS is critical in helping the CEO make better decisions, drive high performance, and hold employees accountable. They have the important role of making the CEO shine and, as Organ puts it, “help lead the company from the shadows.”

Reasons Your Startup Needs a Chief of Staff

Besides the above laundry list of important CoS responsibilities, there are two fundamental reasons why a CoS is critical for your startup as it begins to grow.

1. A Chief of Staff Keeps the CEO Laser-Focused on Important Work

There aren’t enough hours in the day for a CEO to review every item that crosses their desk, let alone address each one. Unfortunately, a long to-do list doesn’t stop new tasks from rolling in (wouldn’t that be nice?). Therefore, when CEOs feel pulled in a million directions, CoS' can take some weight off their shoulders.

One such way is by safeguarding the CEO’s time. CoS' field meeting requests and communications from department heads, C-suite executives, and external stakeholders to determine what makes it on the CEO’s calendar. They’re not necessarily gatekeeping, but instead sorting through the noise and prioritizing requests so the CEO can focus on the projects that are most important to company goals.
And while the boss is focusing on these top-of-mind issues, a CoS can accomplish other items on the business to-do list. This may look like preparing important presentations, gathering and analyzing metrics and key performance indicators for review, and overseeing the implementation of new processes within the company. All of this positions the organization, CEO, and employees for success.

Additionally, while completing tasks may keep business operations running smoothly, it has another crucial impact: preventing burnout of the CEO. By helping manage communications, the corporate calendar, and the health of the company, the CoS greatly alleviates stress and pressure that may present itself physically or mentally in the CEO’s life.

CoS’s share critical responsibilities with the CEO to help ensure the organization is running smoothly and its people are supported.

2. A Chief of Staff Helps Scaling Efforts

A good CoS understands their CEO’s vision for the company, as well as how the CEO wants to get there. For startups that are intentional about growth, headcount planning provides the roadmap needed to reach important milestones and anticipate potential challenges.

However, headcount planning initiatives can become scattered without the right people in the CEO’s arsenal. Bramm admits that before bringing on a CoS, his headcount planning initiatives were fragmented. He needed help coordinating recruiting, screening calls, and making sure Showbie’s hiring processes were consistent.

It’s therefore important for the CoS to have the most current, up-to-date information at their fingertips to help make these decisions. With the right headcount planning software, your CoS can strengthen your hiring process by integrating applicant tracking and HRIS, visualizing department plans, and streamlining collaboration between executives, hiring teams, and managers.

Headcount planning technology will also allow your CoS to partner with your finance team to budget accordingly, whether that’s building out a total compensation package or identifying and avoiding potential skills gaps with a more precise hiring strategy.

In short, your CoS will play an invaluable part when helping complete the many steps necessary to develop a robust strategy for headcount growth.

Coordinate your hiring plan across teams with ChartHop's headcount planning capabilities.

A Short-Lived but Impactful Role

Did you know that the White House CoS is the high-ranking political employee? As shown on the satirical program Veep, the CoS will do just about anything to support their superior. That’s because, as the show’s character explains, she’s the "trouble-shooter, problem-solver, issue-mediator, doubt-remover, conscience-examiner, thought-thinker, and all-round everything-doer".

While CoS' in the business world may not be going to such extremes as the televised political one, they definitely have a front-row view into the CEO’s world. That’s why, according to Organ, many CoS' develop a desire to run their own company.

He’s identified that itch for “something more” to develop around the 18 month mark (which, incidentally, is the same tenure as White House CoS'). He’s therefore proactive in helping his right-hand person, who has done so much for him over the past year, transition elsewhere. Organ explains: “After 18 months of being your stage manager, it’s time to let your CoS lead. It’s [their] turn to take the stage.”

A development plan for your CoS not only focuses on their professional development at your company, but also next steps in their career.

Organ furthers his claim that CoS’s experiences set them up for future success. He says, “CoS’s are massively overrepresented in the top echelons of the Fortune 500, the military, and politics. The same will happen for startups: People who have done the CoS tour of duty will disproportionately become the most successful founders and CEOs.”

Do You Need a Chief of Staff or Executive Assistant?

Let’s pause and play devil’s advocate here. Despite knowing the benefits, some startups choose to not hire a CoS. Why? Simply put, they don’t need one.

Before you cry that the wool was pulled over your eyes, know this: Ahead of hiring a CoS – or anyone, for that matter – you need to understand your organizational structure and plan before expanding your headcount.

And once you start diving into your pain points and what your company needs to scale, you may find that you actually need an executive assistant (EA). Executive assistants are also critical for company growth and alleviating your CEO’s stressors, but in a different way. While CoS’ work is strategic, EAs’ tasks are tactical.

If your CEO has time to plan and facilitate strategy, as well as manage team leads across your organization, you probably don’t need to hire a CoS. In fact, bringing in a CoS in that case may actually blur roles and expectations. Instead, an EA will allow your CEO to continue focusing on high-level priorities while helping monitor day-to-day office operations.

That’s because EAs are hands-off when it comes to strategy. They tackle immediate and short-term needs, such as managing executives’ calendars, arranging travel plans, handling information requests, and planning small-scale events.

In short, before actively seeking a CoS to add to your team, make sure that role is what your company really needs to effectively and efficiently grow.

A Chief of Staff = A Strategic Hire for a Growing Startup

CEOs can’t – and shouldn’t – do it all on their own. That’s why hiring a CoS as your startup begins to grow may be an important hire. This cross-functional position aligns teams to company initiatives, ensuring all employees are on the same page moving forward. By being intentional about your hiring of a CoS, you can not only alleviate needs of the CEO, but provide them with valuable insights to help drive future decisions to help scale the organization.

Interested in learning more about important decisions to help solidify your startup growth and processes?