A common question we get is: “where do Chiefs of Staff come from?” Today, we’ll look at 4 personas that reflect some common pathways by which people become Chiefs of Staff and indicate where they fall on our Leveling Framework.
A persona is a fictional representation of a person based on real facts & figures; furthermore, the personas presented are likely not exhaustive. With that said, these personas are based in part on our community of 800+ CoS as well as around 30 chats we have per week with CoS.
Note: this post is an expansion on the talk “Whence Chief of Staff” that our General Manager Rahul Desai presented at our 2023 Virtual CoS Summit.
#1: Alex - internal promotion to CoS, startup company
Alex is 28 and lives in NYC. She went to UVA for undergrad and then moved to NYC to join a Series B B2B SaaS startup as an SDR, earning $55k base cash and ~$15k of commission. She consistently crushed her quotas, demonstrated aptitude for systems integrations, process improvement, & analytics, and eventually got promoted to RevOps Manager, earning $105k.
After 3 years at that firm, she switched over to a growth-stage SaaS startup for a better paying RevOps Manager role, earning $120k. After 1 year in that role, the CEO of the firm tapped her to become his Chief of Staff, earning $135k (she is Level 3 in our framework).
The CoS role is not only new to Alex but new to her employer. Therefore, there’s not a lot of structured resources for her to learn how to be an effective CoS. She was even responsible for crafting her own job description. This is in contrast to her prior sales roles: she had experienced sales leadership that laid out quotas, training materials, projects, and more.
Now she is dealing with new functions she has no experience in such as HR and Finance; she also hasn’t had to directly handle internal politics and conflict resolution before. She’s also learning new tools such as Lattice, Ramp, Rippling, Carta, and Quickbooks.
Alex sees the CoS role as a transitory launchpad to catapult herself into the C-Suite, but she knows she needs to execute exceptionally to do that. Right now, she’s focused on meeting more seasoned CoS to learn how to dodge common pitfalls and gain mentorship. She spends a good deal of time reading books and online articles about the role and watches a lot of YouTube videos on the topic.
Variants by Company Size
The above version of Alex exists at companies from Series B to IPO. There are Alex variants at early stage (seed - Series A+); that version of Alex is much the same as above, but earns less ($105k), is younger (25) and more junior, and is more resource-constrained. Her employer has even less structure around the CoS role and is expecting Alex to figure things out herself. She is Level 2 in our framework.
#2: Rob - internal promotion to CoS, enterprise company
Rob is 39 and lives in Seattle. Originally from Canada, he got an undergrad degree in political science from the University of Waterloo and an MBA from Stanford. He has spent his 17-year long career as a strategy & operations manager in big tech, initially working at Google, then Facebook, and finally landing at Microsoft. He most recently worked as a Director of Business Operations for the MS Teams division, earning $310k.
The EVP overseeing Teams tapped him to become CoS 3 years ago. He has had a wealth of internal knowledge to ramp up on his role quickly as well as a strong pre-existing relationship with his principal. He is a Level 4-5 CoS.
However, his experience at Stanford made him more curious about startups and how they operate. So he’s always looking to network with startup leaders for his own personal angel investing, corp dev for his employer, or potentially a COO / CPO gig in his future. More generally, he’s looking for a “breath of fresh air” about new business practices and other innovative ideas he can bring back to his principal.
He’s mostly quite satisfied with his work life and is not planning to leave his job any time soon, given how lucrative it is. Outside of work, he mostly likes to spend time with his family.
#3: Nikhil - from professional services to CoS
Nikhil is 26 and lives in San Francisco, but sometimes flies to his company’s engineering hub in India. He attended undergrad at UPenn (Wharton). He did a summer internship at BCG and joined them full-time immediately after graduation, where his sector focus was finance. Over the course of 4 years, he went from Associate ($120k) to Consultant ($170k). He began helping out on some BCG Digital Ventures projects and realized he wanted to make the jump to working in-house.
He reached out to Golden Gate Recruits and eventually found a fit with a hot Series A fintech company as CoS. He took a pay cut to $160k because of his equity upside in the business and his ability to directly drive the business, a distinct change from his prior experience in consulting. He is Level 3 in our framework.
Nikhil prides himself on his ability to land in an unfamiliar situation, orient himself, and execute quickly and effectively. He carries himself like a much older and more seasoned professional, largely due to his professional services experience in front of Fortune 500 CEOs. However, he’s never been responsible for execution before; he used to pass recommendations off to in-house teams. Furthermore, he’s now dealing with the nitty-gritty of corporate functions that his projects didn’t touch, such as HR and IT.
Nikhil aims to become a venture capitalist one day. He sees the CoS role as a way to meet investors, learn about the inner workings of startups, and hone his operational skills. He hopes to lead his firm through hypergrowth and become an investor on the other side of that. Right now, he’s looking for ways to avoid reinventing the wheel; he talks to other Wharton and BCG alumni to get their take from time to time.
Variants by Company Size
The above version of Nikhil exists at companies from Seed to Series C. There are Nikhil variants at late-stage (Series D to IPO); that version of Nikhil is much the same as above, but earns much more ($220k+), is older (30) and more experienced (probably made Engagement Manager or similar in professional services), and wants to ride a rocketship to IPO.
#4: Mary - from EA to CoS
Mary is 52 and lives in London. She attended the University of St. Andrews, where she studied English. She has had a varied career, working in corporate communications, human resources, and accounts payable, mostly at large companies.
Most recently, she was the Executive Assistant and then Sr. Executive Business Partner to the CEO of a family-owned non-tech business, who she had served for 13 years with ever-increasing responsibilities but few changes in title.
When the CEO stepped down to retire and start a family office, he asked her to become his Chief of Staff (a title he heard from another UHNW family) and help manage the office. Her pay is £85k.
Mary has struggled to know her worth but is finally coming into her own with this new title. She’s looking to understand appropriate levels of pay, expected responsibilities, and how to hold her own with executives as a peer, rather than being subordinate to them. Mary is a Level 3-4 CoS.
Mary expects to stay with her principal for many years to come, but wants to establish more of a reputation for herself apart from her principal. She wants to write blog posts, speak on podcasts, and otherwise build up her personal brand. Ann Hiatt (fmr. Exec Business Partner to Jeff Bezos and Eric Schmidt) is one of her heroes.
Variants by Age
The Mary persona is the hardest to pin down by CoS Level. The persona can have a significant executive-level impact or be relegated to calendaring and expense management. Often this correlates to age. A younger, less experienced version of Mary might be Level 1 whereas Mary might get up to Level 4-5 with experience.
These are the most common personas of Chief of Staff that we encounter, along with some typical variants. If you’re feeling imposter syndrome about the CoS role, hopefully this post helps you overcome that! And if you’re curious about what Chiefs of Staff do after they leave the role, check out our Pathways Report here, which lays out the most common career paths for graduated CoS.