Part 2: How to Become a Corporate Chief of Staff

Part 2: How to Become a Corporate Chief of Staff
Maggie Hsu

July 9, 2018

Now that you know more about the role of a corporate Chief of Staff (CoS) from Part 1, you may be interested in becoming one yourself. The good news is that there are an increasing number of “Chief of Staff” roles. A search on LinkedIn turns up over 2,000 Chief of Staff job postings across the United States. The bad news is that every company defines the CoS role differently, so it’s hard to understand what exactly companies are looking for and if your background fits.

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I analyzed the backgrounds of 50 current CoS’s based on their LinkedIn profiles. The key takeaway is that there is no consistent career path for a CoS. However, there are several archetypes that do show up with more frequency:

1. Administrative

Common prior job titles: Executive Assistant (EA), Coordinator, Special Assistant

These CoS’s start working for their executives, or “principals”, in an administrative capacity. Their job responsibilities might include tasks such as meeting coordination and travel booking. Over time, the EA and principal develop significant trust to the point where the EA is given additional responsibility along with the CoS title. They might begin managing other assistants or overseeing larger projects (for example, leading an office move or renovations).

2. Finance

Common prior job titles: Financial Planning & Analysis (FP&A) Analyst, Private Equity Associate, Investment Banking Analyst

CoS’s with financial backgrounds are invaluable at large companies. The CoS might come from the company’s internal finance or FP&A team. The principal, in many cases the CEO, is likely managing several business units and needs help with the annual budgeting process, monthly dashboard reporting, or a struggling initiative. While the CFO is ultimately responsible for these items, the CEO benefits from having a CoS who can provide financial support by tracking down and managing high priority items and analyses.

When I was working at Hilton Worldwide, my then-boss, Paul Brown, oversaw all of the hotel brands (Waldorf, Hilton, Doubletree, Embassy Suites, etc.) and commercial operations (IT, Honors, Sales, etc.) at Hilton, which comprised approximately 15 business units. Every year, there was an annual budgeting process where each division executive would request their budget for the following year. I helped Paul run that process, which took several months and included obtaining the preliminary budget requests, setting up meetings to review those requests, rolling up the budget, analyzing the aggregated budget, and revising the budget as needed.

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3. Strategy

Common prior job titles: Corporate Development Associate, Business Strategy Analyst, Management Consultant, Director of Special Projects, Corporate Strategy Lead

The benefit to a CoS with a strategic background is that they are suited to quickly solving a variety of new problems with limited information and resources, which is critical for many CoS roles. They can scope a problem out, gather data, perform analyses, and make recommendations.

When I was Chief of Staff to Tony Hsieh, he often had special projects that he wanted me to research — for example, starting a hydroponic farm in the desert, or building a luxury porta-potty business. After I performed the initial research and diligence, we would make a no- or go-forward decision on the project. If it went forward, we would transition it to an operational team to execute it.

4. Operations

Common prior job titles: Founder, Product Manager, Head of Operations, Director of Operations

This category of CoS’s are often the most experienced and are identified as high potential business unit leaders. The CoS “rotation” or “tour of duty” is an opportunity for them to gain exposure to the different business units and to spend significant time with the principal, learning how the principal deals with problems, what their key challenges are, and what their priorities are.

Much has been written about the Technical Advisor role at Amazon, which is a classic example of this category. American Express has a similar Director Assistant position. A recent Director Assistant job posting reads:

The DA is responsible for a broad range of activities including strategic, analytic, communications and human capital initiatives to help ensure that business objectives are achieved. The DA is a critical member of the GSM Leadership Team, working closely with them and their teams and key business partners. He or she will possess outstanding strategic thinking, communication, and organizational skills, and will have a proven record of excellence operating independently and within a high performing team environment.

5. People Operations

This is less common, but sometimes CoS’s are hired from a human resources or recruiting background, either internally or externally.

6. Events & Marketing

This is also less common, but sometimes CoS’s are promoted internally from a marketing or events role.

Background and Experience

In terms of seniority, job level, and work experience, there is even more variation. The Chief of Staff could come from any role level:

  • Intern
  • Executive Assistant
  • Coordinator
  • Analyst
  • Associate
  • Manager
  • Director
  • Product Manager
  • Vice President
  • Business Unit Lead
  • Founder
  • Chief of Staff

Out of the 50 Chief of Staffers I looked at, 20 of them (40%) have an MBA (business) degree. However, many of the non-MBAs have undergraduate business degrees, and a few have JD (law) degrees.

15 (30%) of the CoS’s were promoted from within the company, and the remaining 70% were hired into the role from outside the company.

Finally, many CoS’s have some combination of a strategy consulting or investment banking background. It is not necessary to have that specific background in order to be successful in the role, but it is a good proxy for the capacity to problem solve, analyze data and make recommendations, and communicate those recommendations to the relevant stakeholders.

Compensation and Career Progression

The next logical question is around compensation and career progression. While I don’t have specific compensation data from this analysis, I have discussed compensation with other CoS’s. Compensation is highly variable because the CoS role “levels” from, and into, several different roles, so it’s typically determined by the individual’s own background — including number of years and type of work experience.

Note added March 2019: The Chief of Staff Tech Network just released the first-of-its-kind compensation study based on data submitted from 65 of its members, which you can find here. It shows the breakdown of salary vs. factors such as professional experience company size, gender, and more. It’s a great resource for incoming Chiefs who are looking to negotiate their compensation packages, as well as for current Chiefs who are looking towards future raises.

Career progression is similar. Most CoS’s I’ve spoken with suggest staying in the CoS role for approximately 2 years. One potential next step is to run a division of the company, and another might be to attend business school.

Corporate Chiefs of Staff — The List

Here is a list of some current CoS’s:

Abigail Keene-Babcock (Knotel)
Adam Zalisk (Amplify Learning)
Chris Ho (Zuora)
Cody Dales (Deserve)
Dan Garon (Zynga)
Daniel Fetner (Corigin)
David Himmel (Jamestown)
David Mekelburg (Wade & Wendy)
Delian Asparouhov (Khosla Ventures)
Dennis Yu (Betterment)
Emma Franklin Stubbs (CircleUp)
Erica Cruz (Owl Cameras)
Gurjit Kaur (NewtonX)
Hyo Jin Yim (SALIDO)
James Waters (Compass Partners)
Jason Chiang (Common)
Jelena Djordjevic (Thumbtack)
Jennifer Hong (Infor)
Jennifer Redling (Silicon Foundry)
Jennifer Wasson (YouTube)
Jessica Chan (Trim)
Jessica Chervin (Andela)
Jessica Siler (Greatist)
Jonathan Coffey (Qapital)
Jonathan Mark (Bridgewater Associates)
Josefina Hamren (Leif)
Justin Algor (Virtu Financial)
Kara Kubarych (Flatiron Health)
Katelin Wahl (theSkimm)
Katie Szeto (Dropbox)
Leigh Jennings (SoFi)
Lindsey O’Sullivan (Sailthru)
Michael Paek (Clarivate Analytics)
Michael Wu (Carta)
Michelle Wu (Twilio)
Myra Cortado (Industrious)
Peter Rushton (Pinterest)
Phil Opamuratawongse (Floodgate)
Rachel Peck (Harry’s)
Ray Xiong (Dig Inn)
Rena W (Gainsight)
Robert Jay Ross (Purpose)
Rose Bromka (Robin Hood)
Scott Amenta (Spring)
Shehu G (IMAX)
Siv Lam (Eaze)
Sophie Barnett (Jonesworks)
Stephanie Cheng (FreshDirect)
Stephanie Weiner (Merlin)
Sunil Raman (Walmart eCommerce)
Tom Oliphant (Intercom)
Victoria Brumfield (USA Triathlon)

This list is not by any means comprehensive. If you would like to be added to this list (or removed from it), please comment below or reach out to me.

Disclaimers

This was NOT a rigorously controlled scientific analysis. These profiles were pulled and analyzed in order to get representative archetypes. Data was gathered from entering in “Chief of Staff” as a search term on LinkedIn. The data set is inherently skewed because of my network and the profiles that LinkedIn is showing me, and it primarily covers my second-degree connections.

For this initial analysis, I only looked at CoS’s based in New York or San Francisco.

Additional Resources

Advice from Rob Dickins, Chief of Staff at AutoDesk: “I’ve Logged 10,000 Hours as a Chief of Staff in a Large Tech Company; Here’s My POV on the Role” — read it here

Scott Amenta, Chief of Staff at Spring, on “How to get a Job as a Chief of Staff” — read it here, and on the traits of a good CoS — read it here

Emma Ainley, Chief of Staff at 500px, on “What it means to be the Chief of Staff at an A16Z start-up” — read it here

Scott Pollack, who founded the business development community Firneo, on how “Career Tapestries Are Replacing Career Tracks” — read it here


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