How’s this for a job description: You work side-by-side with the founder or CEO. All critical strategic goals and projects have your stamp and input, and you’re included in every high-level meeting with customers, clients, investors and board members. You often travel with the CEO, and have enough currency in the organization to stand in for the boss during meetings with other executives and staff members.
If you guessed chief operating officer, you’re close. The position is chief of staff (CoS). And while it’s long been a power fixture in Washington and other government circles, the position is quickly becoming an effective and key steppingstone in reaching the executive ranks of leading companies and nonprofits. Zappos CEO Tony Shieh has a CoS, as does Tesla’s Elon Musk.
It’s also proving to be an especially effective role for women and can catapult their careers in a significant way. Just consider: Sheryl Sandberg, chief operating officer at Facebook, was Larry Summers’ CoS when he was U.S. Treasury Secretary. Aileen Lee, now head of Cowboy Ventures, a VC firm in Palo Alto, California, filled the same position for Mickey Drexler when he ran The Gap. And Aretae Wyler, former CoS to Atlantic Media founder David Bradley, is now general counsel and chief administrative officer of the company.
Some pretty dramatic cultural and business shifts account for the CoS role gaining prominence over the past decade. For starters, the business of running a business has become more complex. The rapid pace of technological change, coupled with ever more complicated regulations and the likelihood of working with partners, customers and employees all over the world, means CEOs are stretched thin.
That’s been especially evident over the past five years or so as more and more Silicon Valley start-ups add the chief of staff position, experts say. These companies are growing rapidly, making it even more vital for founders to have a trusted point person and confidante who can keep them focused and on track.
“I’ve found that the No. 1 concern of CEOs is complexity,” said Tyler Parris, a leadership coach and author of “Chief of Staff: The Strategic Partner Who Will Revolutionize Your Organization.”
“They want and need someone who can help them manage their time and be the most effective leader they can be,” he said.
As a result, CEOs are looking for help not just with specific business functions but in how they manage their role as head of the organization. A chief of staff fits that bill because although they’re involved in every aspect of the company, the person in this position is ultimately focused on the CEO. “A leader can spend more time on priorities because there is a trusted partner who can do, or delegate, work on their behalf,” said Catherine Berardi, CEO of Prime Chief of Staff, a firm that provides placement, development and coaching to chiefs of staff in private-sector companies and nonprofits.
She should know. Before starting her firm in 2014, Berardi was CoS for Mellody Hobson, president of Ariel Investments, for nearly two years and knows firsthand the value this position brings. “It provides a second set of eyes and ears to better align teams and business units and gives the CEO a close confidante and sounding board,” she said.
The men and women who fill this role share some similar traits. For the most part, they’re college-educated multitaskers, with strong communication and organizational skills. They’re comfortable working in the midst of chaos and have a well-honed ability to read other people and situations, making them especially effective when multiple factions are trying to get facetime with the CEO.
In return they get a bird’s-eye view of what it takes to grow and run an organization and can have real input into decisions that affect the business. This kind of hands-on experience can springboard someone’s career at least five years,” said Parris.
For instance, Aretae Wyler was general counsel and chief of staff for David Bradley, chairman of Atlantic Media, from 2013 to early 2017. Today she is the chief administrative officer for the company. “When you’ve been the chief of staff for the CEO, it’s easier to pivot into an operational role within the company,” she said. “You’re not only getting an expansive view of the whole organization, but you’re also gaining the trust of other business leaders in the company, and that’s critical.”
The payoff for this position is a median salary of $127,000, according to Glassdoor. Salary ranges can vary widely depending on many factors, including education, certifications, additional skills and work experience.
Yet despite the position gaining in popularity — there are 16,000 listings on LinkedIn for chief of staff jobs — there’s still no one direct route or a specific career path for it. “There’s no class to take to become a chief of staff,” said Parris. Some people, like Berardi, have worked with the CEO in another capacity or even at a different company and have developed a good rapport. Others start off in the job, needing to establish trust and open communication within the first few months.
The latter describes the dynamic between Myla Skinner and Jeff Nelson, co-founder and CEO of OneGoal, a national college-access organization that works with students in low-income communities through high school and their first year of college. Skinner has been Nelson’s chief of staff since February and said the role allows her to be involved with every aspect of OneGoal’s operations.
However, before she was able to be effective in the job she and Nelson spent a lot of time talking. “I didn’t know Jeff before I took the position,” she said. “But in those early days, we had to be very thoughtful and intentional in getting to know each other personally first and then building the work from there. He probably knows more about me than some of my closest friends.”
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In addition to making sure Nelson is focused on his most important priorities within the organization, such as fundraising and hiring, Skinner said she provides him with below-the surface intel that he might otherwise miss. For instance, while helping Nelson prepare his opening speech for an upcoming company retreat, Skinner is able to let him know the points he needs to go deeper with and where he might be missing the mark. “I know how to read a room and understand how people are reacting to him or let him know how his delivery is perhaps impacting his meaning,” she said. “I wouldn’t say we’re work spouses. We’re more like work siblings.”
Caroline Pugh is chief of staff for Aneesh Chopra, president of CareJourney, a health-care data analytics firm based in Washington, D.C. While in college at Virginia Tech, Pugh formed a health-care tech start-up and was familiar with Chopra and his work. (He was also the first chief technology officer of the U.S. under President Barack Obama.) She eventually folded her company and moved to Washington, D.C. There she connected with Chopra as he was starting CareJourney and he offered her the job of chief of staff.
“He did a good job of explaining his life and all the different aspects of his position in the company but then said, ‘Why don’t you just follow me around for a day,'” Pugh recalled. “One day in his world made me see how complex it was.” In the two years that she’s been Chopra’s CoS, Pugh said she’s learned how to prioritize his time, putting off conversations and meetings with various stakeholders that can happen later to make room for ones that he needs to have sooner.
“I think the most important task of a CoS is predicting the next thing that’s going to happen,” Pugh said. “At this point in my time with Aneesh, if he calls me early in the morning, I already know why he’s calling and what he’s going to need me to do. We’re on the same page.”
Beyond her work with the boss, Pugh has also seen her responsibilities expand into business development, marketing and public engagement. “I feel fulfilled and challenged every day in my role with this company and in the effect it can have in reshaping health care,” she said.
Her role as CoS also made Pugh realize that there was no network for these professionals to share best practices or even work lessons. “Before I took the job with Aneesh, I cold-called 100 different chiefs of staff, asking to learn more about what the position entails,” she said. She’s since created a CoS peer group in D.C. and is working with Berardi to launch the first online membership network for prospective and current chiefs of staff. The site is scheduled to go live on Oct. 1 and will connect local groups from all over the country and possibly in other countries.
Of course, being a chief of staff isn’t a job suitable for everyone, Berardi noted. After all, “it requires that you prioritize someone else’s wants and needs above your own,” she said. But if you’re looking for one-of-a-kind exposure into how a business operates and the ability to develop a robust skill set that can set you up for any leadership position, it might be hard to beat.”
