16 Jan 2023
What is the CoS role, who is it for, what does day-to-day look like, what doors does it open
1.5 years ago, I was contemplating leaving McKinsey & Company after a great stint of ~3 years. I was lucky to have worked a lot in the high-tech space and the startup bug had definitely bit me. However, having been a generalist throughout, I wasn’t sure what role was perfect for me. This is when I heard about the Chief of Staff role from a close friend. A quick LinkedIn search showed a HUGE variation in the people who had done/were doing this role - across their previous background, avg. tenure before taking up the CoS role, avg. tenure of the role itself, exit opportunities after the CoS role etc. This role specially piqued my interest because coming from a Military family, I have always heard about this role as the right hand to the higher echelons of the military (Chief of Defence Staff, Aide-de-Camp to the President of India etc.).
Having completed a beautiful stint as a CoS to the CEO of an early stage SaaS startup some time back, I wanted to share my reflections on everything about this role, including:
Quick call out that my reflections will be typical of the CoS role at any early-mid-late stage startup. It might vary a bit if you are a senior professional considering the role at a big enterprise, but I believe the spirit of the article should hold, even if the specifics don’t.
Before I get into it, I would like to specially call out - Nishant Modak, CEO at Last9, without whom my journey would not even have been half as amazing.
Let’s get into it:
Simply put, in an ideal scenario: a Chief of Staff to the CEO (or any higher executive, for that matter) is essentially the work shadow or the second brain of the executive. The CoS is expected to make the CEO’s life more productive, with a heavy strategic and execution muscle required on the job. It DOES NOT (or should not) mean picking up the menial tasks that a CEO is forced to do, nor is it a fancy sounding Executive Assistant role (e.g. managing calendars, taking stock of emails etc.).
The CoS works with the CEO as their second brain - be it brainstorming long term strategy, tracking execution of high-impact projects, setting up blue-sky projects from scratch, leading pilots for new initiatives, managing high-leverage processes in the org etc.
Given the high context switching required on the job, a great fit for the CoS role is someone who is genuinely better off at breadth than depth (to begin with) and has experience handling strategic and/or execution heavy projects (depending on the stage of the organisation). It all then boils down to what do YOU want to get out of the role.
For me, the ideal output from the role was the following:
The variables for you might vary, e.g. you might be someone who is 10 yrs into your career and wants to work as a CoS to an enterprise CRO. Irrespective of your context, I still believe the following questions are worth pondering over (in hopefully a decreasing order of importance):
The best answer here, in typical consulting style, is that it DEPENDS. The next realistic answer is whatever you want to make out of it.Going on, I was upfront about my aspirations and expectations from the role with the CEO and he was more than happy to get that viewpoint from me. I typically worked with the CEO on agreeing on priorities of the month (based on company/product strategy, ongoing and upcoming fires, BAU work and some 10x ideas). The goal here was to be a thought partner to the CEO and agree on a priority list TOGETHER. What followed next (and may/may not work in your setup) was literally splitting the list between the two of us (based on our existing workload, fit with the project based on skills and interest). For my own sanity, I used to have a weekly check-in with him to quickly take a stock of where we are on the progress bar and discuss any blockers (but this can change based on working styles of both parties)
Given I was cognisant of trying multiple functions and finding the one that would be a great fit for me, I used to keep that in my mind while deciding the priority list. During my time as a CoS, I was involved in scaling a bottom-ups product 0-1 and therefore experiencing both core product management and growth product functions. I also was working closely with the outsourced demand gen. and BD team and setting the process for building it in-house and got a great view point into the sales function. As an early stage startup that is always crunched for resources, I was also running point on the finance side of things (monthly PnLs, fundraising requirements, investor reports etc.). Briefly working with the leaders from the marketing and customer success functions also gave me a feel of what that life looks like. Heck I even organised our company’s first offsite and became the talent acquisition POC for a few important roles (so a customary check check on HR and Admin as well ;) )
For most projects I can safely say that the strategy and planning will have to be owned by the CoS, just like how it would be for a CEO owning a particular project. Your job is easier that way in a startup with a lot less senior stakeholders (and therefore less office politics and optics to navigate). If however, you are the CoS in a large-scale enterprise and one of your projects involves working with an existing leader (e.g. a BU head), you will also have to carefully navigate that relationship, and be the strategy and planning owner while not overshadowing the existing leader (a huge reason why large-scale enterprise CoS’ typically have many more years of experience than a startup CoS). The execution bit of the project can either be co-owned by the CoS or outsourced to a vendor/sub-team in the org. The CoS is then typically involved in tracking progress, solving blockers, streamlining the process and moving on to the next high-leverage priority of the company.
Another important role of the CoS (and an unofficial part of the JD) is to act as a second pair of ears for the CEO. Ideally the CoS is a little lower on the hierarchy table and therefore should bring some ears-on-the-ground insights for the CEO. I felt that was an immensely huge contribution for me as a CoS as I was able to bring a unique view point on the table - essentially capturing the pulse of the organisation. It also became a huge trust building exercise between the two of us during my time as a CoS.
This is probably an interesting section for a lot of folks reading this post. When I was considering the CoS position, I was very clear that I wanted to (quickly) understand what functional role is the best fit for me. Having a close relationship with a senior sponsor in the organisation gives you the freedom to truly shine at whatever you are picking up. It also allows you to build a trust based relationship where the executive is batting for your success - be it in the form of a fast-tracked senior position at the company or any where else that you want to go, after having identified your interest area. Again, the answer is it truly DEPENDS, but in most cases the CoS role is a way to fast-track your path in the industry while having an absolute gala. If you come from a strategy background with a decent # of years behind you, it can be a great place to say transition into a complementary business head type role. Or if you are a product marketing persona and do a short stint with the CPO, it can be a helpful transition into the PM path.
The CoS role is truly truly great as a stepping stone into any function, while allowing you to get your hands dirty with the organisation’s real challenges. However, do treat it as a stepping stone and a phase of optionality. Experience everything but with the mindset of getting into a specific role that is best aligned with your interests. I was lucky to have found Product & Growth as the vertical that best aligns with my skillset and interest. I wish the same on you, fellow reader :)