Three Pieces of Expert Advice for Chiefs of Staff
March 2, 2021
Three Pieces of Expert Advice for Chiefs of Staff

Since starting Elate, our team has noticed a few trends taking place in tech. One trend we’ve become bullish on is the difference a Chief of Staff can make in guiding a company on their growth journey. Gone are the days when this role was reserved for only government officials or Fortune 500 companies. Whether it’s building critical processes that allow your team to scale, or their ability to align every member of the organization, it’s a role we’re confident will only grow with time.

In fact, we are so bullish on the rise of the Chief of Staff that we started our series off with three different leaders who are in the position today. Across every single conversation, we came away impressed with each individual’s ability to diagnose new problems and create unique solutions for each of their organizations. 

From these conversations, we realized that the amount of resources that exist for anyone in the Chief of Staff role are few and far between. Outside of leaning on individual networks, and sheer willpower to get the job done, it became clear there weren’t many avenues a Chief of Staff could turn to for advice. That’s why we made sure to ask each Chief of Staff we interviewed the advice they’d give to anyone getting started in the role. Read on to learn what they had to say.

Sydney Cummings, Chief of Staff at Terminus

Our first leader we’re spotlighting is Sydney Cummings. Since taking on the role in September of 2019, she’s seen Terminus grow exponentially, acquiring three different companies along the way. Through this growth, there have been many new challenges she’s had to face head on with other leaders. Listen to her biggest piece of advice for anyone in the role below:

Part of the role of a Chief of Staff is working directly with leaders across the organization. Each department is likely accustomed to tackling problems from different angles. It’s your job as the Chief of Staff to present solutions to these problems that arise. As Sydney shares, this can be a very iterative process, and it’s important to come in with a team mentality and never let your ego prevent you from accomplishing the goals you’ve set out to achieve.

To listen to our full interview with Sydney, click here.

Emad ElShawa, Chief of Staff at Fundbox

The next leader we interviewed was Emad ElShawa. Like so many others who take on the role of Chief of Staff, it was an opportunity that presented itself as Fundbox grew. After working in Operations, Emad’s ability to connect with every individual throughout the organization made him a clear candidate to take on the position. Here’s what he had to say to anyone that’s just getting their start in the Chief of Staff position:

If you look at any Chief of Staff job description, it’s likely that you’ll find the words alignment and accountability littered throughout. If you want to maximize your potential in the role, networking throughout the organization, not just at the leadership level, is a great way to drive results. Helping individual contributors understand how their work ties into the bigger picture of what your company is working toward is a great place to start making an impact.

To listen to our full interview with Emad, click here.

Brynn Michelich, Chief of Staff at Jellyvision

Our last leader, Brynn Michelich, has truly done it all. Brynn got her start in Product, and continuously elevated her game as her role shifted to SVP of Product, COO, and now the Chief of Staff at Jellyvision. Part of what led to Brynn’s ascension through the ranks was her eagerness to take on projects, even if she didn’t have domain expertise in the subject. Below, she shares why it’s the same piece of advice she offers to anyone new in their role.

When you’re in the Chief of Staff role, you’re forced to look at the business from every angle on a daily basis. The best way to get exposed to how different department leaders tackle new challenges is to raise your hand and offer help. You may not know the exact ins and outs of what you’re solving for, but those you’re helping will be thankful for it, and you’ll gain valuable insights going a layer deeper into the business.

To listen to our full interview with Brynn, click here.


Sydney, Emad, and Brynn might tackle their jobs from different angles, but each one of them has developed a style that works for them. As you take on the Chief of Staff position, be sure to play to your strengths and find your own formula for success. Whether it’s being vulnerable in the position, leveraging your own company’s network, or being the first to volunteer, we’re confident you’ll be able to carve your own path and find an avenue that works for you.

Want to hear from more Chief of Staffs? We’ve got you covered! On next week’s episode of Aspiring Ops, we’ll be interviewing Chelsey Krisay, Chief of Staff at Trainual. Like so many other leaders we’ve spoken with, Chelsey took a non-traditional path into operations and we’re excited to provide a platform for her story. Stay tuned for more next week!