The what and why of how I became Chief of Staff

9 min readMay 7, 2021

Chances are that you’ve heard of the “Chief of Staff” title within a political or military context; arguably the most notable instances can be found in the US government and military with the White House Chief of Staff and Joint Chiefs of Staff. However, this title is becoming increasingly popular in the private sector as well—particularly in the tech sector—with many tech CEOs hiring folks for this role (chronicled in Washington Post here). The main reason for this newfound demand particularly in the tech sector is due to the fact that tech CEOs in particular may not always have the full bandwidth to deal with all of the various demands of the role in the context of a 10x (or even 100x) scaling startup. In this context, Chiefs of Staff (CoS) effectively act as a gatekeeper and force multiplier, ensuring that CEOs can remain efficient by filtering out the noise so that they can focus on key priorities in the given lifecycle of their business.

There are many articles out there that define the role of Chief of Staff as well as explain their raison d’etre, so rather than spending time coming up with my own definition here, I’d like to use this piece to reflect on exactly how I came into this role as a way to illustrate a potentially interesting career path for other tech sector professionals. Before doing that, let me share three categorical definitions that help to shed some light as to what exactly is in scope for this relatively ambiguous and idiosyncratic role.

Defining the role

1. Filling in organizational gaps

At an earlier stage company, a Chief of Staff may spend part of their time filling in gaps in the organization, such as working on partnerships when there is no business development team yet, or working on executive recruiting when there are high-priority hiring needs.

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As anyone who has worked at an earlier stage startup can attest to, human capital is one of the biggest challenges to scaling a business. In the early days, you have less capital and lower brand name recognition so can lose out to larger players that pay higher salaries and appear more attractive on CVs. This oftentimes means that the CEO and other early founders must don many hats, and depending on the organization this might not always be sustainable. Hence, in an earlier stage company a CoS might fill in for organizational gaps. For instance, if there’s a missing Head of HR, the CoS may need to focus on recruiting and performance reviews.

As the company matures and roles get filled, there will still tend to be cross-functional special projects that emerge from time to time, which the CEO won’t always have the bandwidth to initiate and project manage from inception to implementation. These types of situations benefit from having a CoS to fill in such organizational gaps.

2. Supporting the CEO

CoS can oftentimes get confused with executive assistants or personal secretaries, which makes sense given the fact that even the White House Chief of Staff actually grew out of the former role of “Personal Secretary to the President of the United States”. However, the important distinction here is how proactive and how much initiative does the role require given the stage of the business as well as the needs of the CEO…

As you can see from the above table, a “Level 1” vs “Level 3” CoS are two very different jobs in nature. At “Level 1”, the CoS is simply supporting the CEO in an administrative capacity, while at “Level 3”, the CoS is supporting the CEO as a thought partner.

3. Product Manager of the organization

“My responsibility is to treat the company like a product, where employees are the user. Like a product manager, I spend my days thinking about what we should build and improve on, owning the components that make the company’s culture and productivity come to life,” says Fishner.

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This last definition is something that I’m quite fond of. When we think about Product Management as a function, it’s primarily about driving user value by balancing the business, technical, and design requirements of a product. While PMs are typically focused on external users, PMs who focus on internal users are equally as important, particularly in a growing, complex business that requires cross-functional collaboration. It’s important to also consider employees as a distinct set of users in your business so that you can also consider how to create value for them, perhaps it’s through the introduction of new cadences, new dashboards, new channels of communications; these decisions impact productivity and culture immensely, especially in the advent of remote working.

My journey to becoming a Chief of Staff

For the record, I never had an explicit target of becoming CoS, it sort of became a natural outgrowth of my responsibilities…

Clarifying a career north star

After graduating from business school, I headed off to Silicon Valley to learn more about the technology sector—in particular, perhaps due to my background in economics, I was keen on learning more about data—starting out at Oracle. Though I learned a ton and began cultivating a passion for data analytics here, I realized that I wanted to apply these skills on something more personally meaningful to me. Having completed an internship in microfinance while in college, I decided that financial inclusion and FinTech was where I could make the most impact with my career.

Supporting and amplifying the CEO

Thus, I went to Kiva where I worked on their “Strategic Initiatives” team, which is basically a sort of “CEO Office” role. I worked on a few special projects, including data analytics for a new social impact model, business development and underwriting for a new portfolio, as well as product managing an experimental new product. This experience taught me the importance of cross-functional collaboration, project management, and translating strategic vision into implemented realities with few resources. Though I didn’t realize this at the time, this would prove to be tremendous learnings as it relates to grooming me for a CoS role.

Filling in organizational gaps

While Kiva was one of the best times of my life, it was a non-profit and I was keen to gain work experience at a for-profit FinTech startup that was targeting an exit, while of course still being mission-driven. Luckily, a college friend referred me to a unique company called Oportun, which was gunning for an exit (full disclosure: they ended up IPO-ing in 2019). At Oportun, while officially on the “Analytics” team with the primary responsibility of running growth experiments, due to an organizational gap, I ended up also owning digital marketing implementation. Due to this, I had to rapidly get up to speed on Google Ads, Facebook Ads, and SEO. Again, while I did not realize this at the time, this ability to adapt quickly was an important skill to learn towards becoming a CoS later on.

Product Manager of the organization

During a family visit in Indonesia, I had a chance encounter with a former Kiva connection who mentioned that his startup, Mapan, was getting acquired by Gojek, and he was setting out to build out inclusive financial services products on top of the ride-hailing & food delivery app platform. This seemed like a once-in-a-lifetime opportunity to support scaling up Indonesia’s first unicorn in a business area that I was particularly passionate about so I ultimately decided to take this offer. Officially, I led the “Business Intelligence” function but this quickly expanded into de-facto leading risk & fraud, data engineering, as well as growth. This resulted in my team growing quite rapidly from just 2 direct reports to 15+. As someone without prior team management experience, I had to quickly learn how to best manage people in an efficient, effective manner. I ended up implementing a hybrid Agile/Scrum/Kanban framework, organizing my team into squads and running frequent cadences (daily standups, tactical cross-functional meetings, and bi-weekly retrospectives). This experience taught me valuable management lessons: “if you think of your team as end users, how are you optimizing user delight through the systems, processes, and culture that you establish?” and “what type of role should a manager play in order to not micromanage yet still give sufficient structure and guidance to drive deliverables?”

Tying it all together to become CoS

After over 2 years at Gojek and scaling from 20 to 200 people within our division, I decided that I wanted to experience an earlier stage startup again—though still within the inclusive FinTech space—hence I moved to Pintek, a lender uniquely focused on the education sector. At Pintek, I started off leading the “Data & Analytics” function, effectively establishing the team from scratch by architecting our data environment, roadmapping our needs from a data perspective, and making our first hires. My overarching objective was to “automate and streamline” as much as possible. As we began to execute on the roadmap, however, I realized that there appeared to be a slew of data governance issues that prevented us from building the pipelines, dashboards, and other data products that we needed to automate processes. Upon closer inspection, though, what superficially looked like data governance issues turned out to have a much deeper root cause.

Lesson: what might seem like a data governance issues 99% of the time has a root cause in some human error resulting from a faulty SOP, a backend logic issue that was shipped without proper QA, or some other gap in an internal system.

These bottlenecks also coincided with organizational re-shuffling and so overnight I found myself de-facto leading the Product function. With no prior deep experience in Product Management, I focused on fundamentals, asking and solving the following question: “how can this function better collaborate with cross-functional stakeholders to drive efficiencies, while effectively prioritizing and driving technical development with the Tech team?” After discussions with the CEO, this unleashed an organization-wide transformation where I drove adoption of Atlassian products such as Confluence and JIRA, re-designed our meetings through minutes-of-meeting templates, and mandated retrospectives to ensure continuous improvement feedback loops. Given this evolution in role, I was officially given the CoS title, wherein I continue to double-hat as both VP of Data & Analytics as well as Chief of Staff.

Currently, one of the initiatives that I am most proud of driving as CoS is Pintek’s admittance into Google’s startup accelerator program; consistent with a CoS’s main mandate, this program will hopefully serve to improve the way that our startup operates across the various functions.

Conclusion

So, what to make of all this? CoS is a generalist-type role that allows visibility into multiple areas of a business, hence it’s no coincidence that a lot of CoS talent have backgrounds in consulting since you’re effectively serving as an internal consultant to the business. While I initially started out my career thinking that I’d be an “I-shaped” person or a specialist, through experiences, I’ve seen my role grow into a “T-shaped” person, meaning that I still have my respective specialty (data analytics in my case), yet have shallow capabilities in other functions such as Risk, Product, Marketing, Finance, Operations, etc. Thus, if you’re in a particular function yet want broader exposure to the business, this career path could indeed make sense to you.

Shifting gears towards the organization’s perspective, I think that the CoS role is becoming increasingly important given several factors. Culture and way of working are things that startups tend to take for granted, allowing the long hours in a cramped office (or garage) drive that. However, given remote working conditions there needs to become more intentionality with regards to how this is created. Furthermore, if a startup is operating in a multi-cultural, dynamic environment (i.e. running a startup in an emerging market like Indonesia), then having a CoS becomes even more relevant.

Bottom-line: if you are an early stage, dynamic, multi-cultural, remote-based startup, you should strongly consider creating a CoS role. Better yet, if this CoS is someone that can double-hat with one of the pre-existing functions that is particularly important to your company’s stage then consider nominating someone to double-hat the function. For instance, let’s say you’re in the process of driving a massive re-factoring of your technical architecture, in that case it might make sense to have the Head of Tech double-hat as CoS.

If you’ve made it this far, thanks so much for taking the time! Also, if you’re interesting in joining an early stage, mission-driven Indonesian FinTech startup that’s uniquely focused on the education sector, do check out our careers page here and reach out to me at max.hasan@pintek.id with your CV.

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