Chief of Staff Roundtable by WaterBridge Ventures

We had the pleasure of hosting several Chiefs of Staff and Founder's office professionals at the WaterBridge Ventures office in Bangalore office. They represented the entire spectrum of companies, right from Series A startups (Newtrace, SatSure ), scaled ones ( Leap , Simpl, Ninjacart, RentoMojo), unicorns (slice, Razorpay), pre-IPO (Swiggy) to public companies (Ola Electric).

The free-flowing conversations at the invite-only, closed-doors roundtable touched upon a broad range of topics, interspersed with healthy, animated debates.

Are you a "Chief Shepherding Officer"?

The visibility that the Chief of Staff role offers is second only to the founder(s) in the company. They spend a lot of their day-to-day liaising with the investors, preparing MISes for reporting and are often tasked with getting things done.

Often, founders task their CoS with whatever is necessary and urgent. There is no fixed job description - one could be dousing fires everyday, while ensuring that the ship continues to steer with broad mission of the company intact.

All of that involves continuous communication across the breadth of stakeholders. With so manny agenda items on the plate, often the CoS has to rely on the work product of many other members of the organisation.

The constant nudges to adhere to timelines, continuous prodding to debottle-neck systems, and the acting as a conduit for strategic communications, might seem akin to being a shepherd.

A shepherd who has the respect of the organisation, and the trust of the founders to steer the band to successful outcomes.

Most strengths have corresponding weaknesses

Should a CoS be hired externally, or should be groomed from within? There is no right answer to that. But whatever be the case, there are traits that set a CoS apart from his peers, and in the organisation.

A key aspect of the job is that deliverables are mostly expected as of yesterday. And there are quite a few of them. Some of which you don't even like to do, but are important.

In such situations, recognising the tasks that align with your interests (say, Product & Tech), the ones that need urgent attention (say, running a paid campaign to cover sales target shortfall), arranging them both in order of priority (from P0 to P3) and then focussing only on the P0s - would drive maximum impact.

The P3s can be delegated to a team that is hired under the CoS, that leads the larger founder's office charter. As the company scales, the founder's office also scales in proportion.

The transition of every CoS from a pure play individual contributor (IC) to a seasoned people manager is underway the moment a company raises Series B.

While it is easy to delegate tasks and embrace the people manager role, the core strength of CoS remains their ability as an IC. Commanding respect in the organisation comes largely from the demonstrating the skills required of an IC - thorough research backed with data, ability to break down problems to the smallest chunks and ability to rally the team in times of distress.

This strength should never give way to weakness. Some tenured founders have seen this play out multiple times and set up their team for success with this in mind. In most other cases, the learning curve is mutual.

It can get lonely sometimes, but there are ways to cope.

Ask, Ask, Ask - Until you get the answer you want

Cross-functional roles offer a breadth of exposure, but also take away the luxury of spending time with a vertical and gaining depth.

In such situations, who can one uphold their primary responsibility of engineering outcomes?

The answer lies in asking the right questions

The stakeholders are seniors individuals with years of experience behind them. They are often subject-matter experts in their profession. While the CoS might come with an ask that seemingly sounds bizarre, he also comes with the context of the ask.

Context makes all the difference, and aligning the organisation leaders on shared context is a key, yet underappreciated part of their jobs.

Developing a mutual respect with the colleagues is the bedrock of this role. Knowing the strengths and weaknesses of every stakeholder is crucial to understand what is being communicated between the lines. The founder(s) is pre-occupied to decipher these nuances, leaves the trusted lieutenant to recognise and relay these subtle undertones.

Never did I ever ... Say "I told you so"

Unless expressly stated, no founder expects their CoS to be a ‘yes man’. They're expected to bring in the perspective from the ground (market) and the trenches (organisation) into meeting rooms. What happens when these perspectives clash with that of the founder?

Navigating these moments hinge a lot on the kind of interpersonal relationship a CoS has with the founders. It varies from company to company, founder to founder, and is dependent on the stage of the company and the cycle of growth.

But what stays constant is the ability to allow the founder to trust their gut. While one can pick up the reins and attempt to contain the unbridled optimism of founders, it is important to recognise that this irrational optimism is what got them started to begin with.

So disagree and commit. Instead of appearing smart in failures, be the one who tries a lot quickly, and gets to know what works and what doesn't.

Over time, a mature CoS figures out when to dial up the enthusiasm, and when to dial it down. This ability bears fruit gradually, when you're the trusted sounding board of not just the founders, but also the leaders who approach independently for advice.

At the end of the day, a CoS is the only one who has the vantage to constructively question decisions. If not them, then who?

What does a Chief of Staff go on to do?

The role inculcates so much versatility, that there are examples galore of CoSs going on to start successful companies as founders (such as Saurabh Jain of Stable Money ). Given the unprecedented knowledge of the intricacies of the startup, they can pick up a vertical within the organisation and lead / build it from 0 to 1.

With all the investor facing hours spent, one can pick up the M&A & Corporate Development vertical of the startup as it scales beyond Series C. The industry knowledge gained in the period can even help them consider investing as a formal career.

There is really no dearth of options for one to consider.

Heartfelt gratitude to everyone who participated in the roundtable! Faiz Ahmed Mulla, Gayathri G, Harsh Dubey, Mohit Jain , Manavala Thambi K T, Manasa Gonchigar, Mitali Raju , Naveen Sowriraj, Baba Prasad Nath , Sapna Goyal , Olivia Chowdhury, Pranav Srinivasan, Prakhar Agrawal, Akash Jangid, Utkarsh Singh, Rakesh Venugopal , Suryansh Bhargava, Surya Sudheer Meduri ,Vishnu Acharya, Gautam Ravi . We hope that this is the first of many more to come!

If you're a Chief of Staff, and up for a no-agenda chat, ping Raj Nayan Datta at raj@waterbridge.vc!