I Hired A Chief Of Staff – You Should Too

Chris Ronzio

July 30, 2021

Outside of the software world, I’ve always known chief of staffs to be something politicians have – or maybe even big conglomerates. But I never imagined it for my own company. In all honesty, another chief executive sounded like too many cooks in the kitchen. 

But after reading something from the First Round Review, which explains how the chief of staff works behind the scenes to make the CEO a superhero, I reconsidered. Because I needed someone to help take care of my day-to-day tasks and help execute my vision. That way, I could focus on growing the business.

At the time, I was looking for someone to bridge the gap between executive assistant and chief operating officer (a role we didn’t quite need yet). I just didn’t know the role fell under the title “chief of staff.” This person would have to understand Trainual inside and out. They’d have to juggle a lot of things at once. And mostly, they’d have to compliment my work style as the CEO. 

Luckily, I knew the perfect person for the job. 

Meet our new-ish chief of staff at Trainual

Chelsey Krisay has been with Trainual since my consulting days (AKA before the company was officially “Trainual”). And she’s probably had every job in the book (besides software developer) along the way.

Chelsey Krisay, the first chief of staff at Trainual
Chelsey Krisay, the first chief of staff at Trainual.

In the early days, she handled all of our administrative tasks. She’d organize and orchestrate my client calls. She’d schedule everything on my calendar. And, eventually, she started joining me on consulting gigs to lighten my workload. 

We’d interview every employee at a company to see where they could be more efficient and organized. Then, put together a report recommending ways these businesses could run better – oftentimes by implementing software.

When we decided to stop consulting and go all-in on Trainual, she became the first customer success slash sales rep. She helped my brother and our CMO, Jonathan Ronzio, get our marketing efforts off the ground. And most recently, she was our operations manager. 

Because Chelsey has been with us for so long, she deeply understands every corner of this business. And for the past year or so, she’s used that knowledge as our chief of staff. 

Today, she works behind the scenes to bring people together, solve minor issues, and mediate disagreements. In other words, she acts as a proxy – filtering out everything I need to know (and taking care of everything I don’t). 

It’s been a game-changer having her as my right-hand woman, which is why I want to share my decision to create this position. And if you’re a founder or CEO of a fast-growing business, chances are good you face these same three challenges. So, before you become the bottleneck, here’s why you should consider adding another chief to your executive office:

1. You need a liason to duplicate your efforts

Almost a year ago, Chelsey and I had the opportunity to talk to the Arizona governor’s former chief of staff, Kirk Adams. And all politics aside –  it was a valuable experience understanding how his position had worked with the governor. Plus, we used what we learned to solidify what Chelsey’s new position would take on. 

Kirk told us that being a liaison between the governor and his other cabinet leaders was his primary responsibility. And in a company, a chief of staff does pretty much the same thing. 

The chief of staff doesn’t have any direct reports (except maybe an executive assistant, or in our case, an office manager). They work almost exclusively with the CEO. And collaborate closely with other departments on behalf of the CEO.

For example, if someone needs approval on something, they run it through Chelsey, and she acts as my eyes. These meetings give her a pulse of what’s going on across the organization. And she relays the critical information to me. That way, I know what upcoming decisions need my help and what red flags need my attention.

In other words, Chelsey is constantly on the lookout – and she sounds the alarm only when absolutely needed. Otherwise, she takes care of the tasks that need my approval but not my attention. And that frees up my bandwidth so I can solely focus on higher-level priorities. 

2. You need someone to keep you organized and focused

Chelsey also helps keep me organized, so I’m always heading in the right direction. Every morning, we chat through my schedule, cover the random ideas I had the day before, and discuss what projects I need her to tackle. 

She even has a synced copy of my digital notebook – where I dump all of my ideas and upcoming tasks throughout the day. So, it’s almost as if she’s in my brain. And that’s key for this position. The closer a chief of staff can get to operating as the CEO, the more successful the role will be. 

As a result, Chelsey takes on the recurring responsibilities that would otherwise distract me from growing the company. For example, she plans all of our Monday company-wide meetings, quarterly all-hands, and leadership planning sessions. Plus, she schedules board meetings, outlines the deck, and pulls in key players for big discussions. 

The Trainual leadership team at a retreat the chief of staff planned
The Trainual leadership team at a retreat the chief of staff planned.

This takes a few huge responsibilities off my plate. And it keeps my attention on things that only I can handle. That way, I’m even more productive with the limited time I have every day. 

3. You need someone to help execute ideas

The last critical part of the role is execution. Because Chelsey is my right-hand woman (and constantly inside my brain), she takes my ideas and makes them happen. Meaning, she taps the right people in and keeps track of the progress. 

For example, we recently raised a $27M Series B round. But to get there, we had a pretty intense Asana project to keep track of where in the process we were at with each VC firm. Chelsey managed this board. Then, before each call, she’d give me a status update, give me a run-down of the firm, and prep me. 

She’d also join me on these calls. That way, she could delegate any follow-up tasks to the right people, ensure we met all our deadlines, and eventually close the round!

But Chelsey also keeps larger initiatives on track. Every year, we set OKRs (objectives and key results) at the start of quarter one. Then, she keeps our team’s attention on them and tracks where we’re at. Admittedly, it’s easy to get lost in the chaos of abundant opportunities. So, she grounds our leadership team and ensures that what we’ve committed to actually gets done.

Before having a chief of staff, it seemed impossible to act on all my ideas. There was always bigger fish to fry. But now, Chelsey can take my best thoughts and turn them into reality. And that’s not only good for our business – it’s also great for my creativity and innovation.

One of Chelsey’s biggest contributions to the company is helping move things along. She brings a strong team together and ensures that they meet the goal. She addresses any of my needs or problems, supporting me to help make decisions. And she cuts things off before they get to me – which is critical for focusing on what matters as a CEO. 

Listen, if any of these needs apply to you, it might be time to add another cook to the kitchen. Because with a chief of staff, you can clone yourself as a company leader. And, as a result, you can improve your efforts’ efficiency and effectiveness. That means you can cook up better results, promote more growth, and finally focus on scaling your business! 

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