Best Practices

Why every growing startup needs a Chief of Staff

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by ChartHop Team

November 24th, 2020

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The ChartHop Team

“I can feel it beginning to drift,” says Colin Bramm, CEO of Showbie. The Canada-based software company builds creative solutions to help educators go paperless in the classroom, and recently raised their Series A this past August. It’s a milestone for any startup, and the growth excites Bramm.

But it also gives him pause.

“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.”

For startups, so much can happen at once. The problem is, the CEO can’t be there for all of it. Even the best efforts to keep a handle on growth can give way to fractured processes, miscommunications, and uninformed decision-making. Looking at what’s to come for Showbie in the next year, Bramm knows what he needs to avoid these risks: a Chief of Staff.

Industry experts agree that the role of a Chief of Staff often varies by company, but for Showbie, Bramm has a clear idea of what his Chief of Staff looks like. “Someone to sit next to me and be very mindful of these gaps that are forming and jump in,” he says. “Someone that can kind of give me a lot more muscle to help lift up the organization through this period.”

While a Chief of Staff functions as a CEO’s most trusted right-hand person, they can also benefit the company at a time when help is needed most.


With their CEO-level view, Chiefs of Staff help CEOs prioritize work, foster key external and internal relationships, and with the right tools, improve processes and decision-making.


A Chief of Staff keeps their 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 ask. But that doesn’t stop items from rolling in. Stakeholders want meetings, department heads need decisions made, and for a startup, there are important hiring needs to consider.

When startup CEOs feel pulled in a dozen different directions, the risk of burnout becomes very real. A Chief of Staff can help them avoid that.


A Chief of Staff safeguards their CEO’s time. They field meeting requests and communications from department heads, C-level execs, and external stakeholders and determine what makes it to the CEO’s calendar. The goal is to sort through the noise and prioritize requests so that the CEO has the time they need to focus on projects that are important to the company’s goals.

COS responsibilities

While their CEO focuses on these top-of-mind issues, a Chief of Staff can accomplish other items on the CEO’s to-do list. They prepare important presentations, gather and analyze metrics and key performance indicators (KPIs) for the CEO to review, and might even oversee the implementation of new processes at the company. They can also position their CEO for success.

It’s not often that an idea is ready to go at conception. It takes cultivating, research, and planning. It can also require keeping an eye on a lot of moving parts. With everything a CEO already has on their plate, juggling new or half-formed ideas might be too much, but not for a Chief of Staff.

Having an understanding of a CEO’s priorities for both their role as a CEO and their vision for the company makes a Chief of Staff uniquely qualified to work on the beginning stages of an idea.

If it turns out the idea doesn’t amount to anything concrete, they can put it aside. But for those ideas that have the potential to turn into something great, the Chief of Staff can invest time in research and planning and then pass on the idea to their CEO once it’s ready.


A Chief of Staff works as an extension of the CEO

If a CEO could be in two places at once, they might try. Since they can’t, having a Chief of Staff familiar with the way they make decisions and conduct themselves just might be the next best thing.

Consider an important industry event. If a CEO can’t attend, the Chief of Staff can go in their stead. For a startup, this type of networking event is crucial. Connecting with other industry professionals can lead to strategic partnerships, and a chief of staff aware of where the CEO wants to take the company can help identify and cultivate those key relationships.

A Chief of Staff can also help close communication loops.


As a startup grows, there are so many conversations happening at once that it can be difficult for a CEO to keep up with every single one. A Chief of Staff can send important follow-ups, circle back on conversations, or request more information on behalf of their CEO. This extra set of eyes makes it so the CEO never has to worry about a ball being dropped.

At Showbie, Bramm recognizes the key role a Chief of Staff would play as his proxy.


I need someone who has the capacity to shift focus, go deep, and work on something on my behalf. Especially in the absence of having some of those leaders that we’re going to need to bring in to ultimately manage or lead some of these specialty functions in the company.

Colin Bramm, CEO @ Showbie

A startup CEO wears many hats, from hiring to fundraising and strategic planning, but as we mentioned earlier, they don’t always have the time or the bandwidth to assume all those roles at once.

The right Chief of Staff can pivot from one role to the other as needed, meeting with important stakeholders and making decisions based on how they believe their CEO would.

For a startup, this CEO extension is important. For one, a Chief of Staff ensures that work keeps moving. Projects stay on task because a chief of staff can provide the input needed from the CEO. They’re also the CEO’s eyes and ears in the company.

“A good [Chief of Staff] is constantly monitoring the health of the organization and making specific recommendations on how to improve it,” says Mark Organ, CEO at Influitive.

A Chief of Staff 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.


A Chief of Staff helps streamline processes for the company

A good Chief of Staff understands their CEO’s vision for the company—and how the CEO wants to get there. As startups begin to grow, Chiefs of Staff can be mindful of opportunities to put in place new practices or tighten up existing ones to keep the company running smoothly.

Take planning. For startups with the intention of growing (and fast), planning provides the roadmap needed to reach important milestones. It also helps companies anticipate potential challenges. But how a startup CEO and their team come up with a plan differs.

Some use spreadsheets, while others lean on conference room whiteboards or Post-It Notes. But the takeaway is that there are always a lot of processes and tools at play.

Showbie wanted to level up their planning game. Bramm implemented ChartHop in an effort to streamline org planning, and it’s already revolutionized how he and his team visualize growth. “It’s the main tool that [the Chief of Staff] and I will use together as we’re building out the organization over the next year.”

Planning requires personnel growth, a particular area Bramm wants his Chief of Staff to focus on. “It’s very fragmented at the moment,” he confesses. “Coordination of recruiting, those screening calls, and how we’re keeping our hiring process consistent.” ChartHop can help.

Scenario Overview

Coordinate your hiring plan across teams with ChartHop's Headcount Planning capabilities.

With ChartHop, Bramm’s Chief of Staff can tighten up their hiring process by integrating their applicant tracking and human resources information management systems.

Applicant and employee data automatically populates in ChartHop, giving Bramm and his Chief of Staff a holistic view of their current state. They can create multiple growth scenarios for the next year, like what it would look like to bring in a head of human resources in four months versus eight and how the team that supports that role might take shape.

Chiefs of Staff can leverage tools like ChartHop to unite platforms and centralize information. It creates a single source of truth that departments can use to collaborate and also helps make processes more efficient.


A Chief of Staff makes an impact when it is needed the most

Chiefs of Staff might not hold that role forever. Some individuals move on to other leadership roles in the company, or sometimes the role evolves into something new. But for a startup, a Chief of Staff can make a valuable impact on the CEO and the company during a critical time in their history.

That’s how Bramm sees it. “I don’t think it’s a permanent position in the company... but at least, at this moment, I think it’s the perfect role to have during a post-Series A phase.”


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Written by ChartHop Team

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