My experience as a Chief of Staff and my new title now

People always wonder what a Chief of Staff does. So do I, still.

Before we jump in, I want to say a huge thank you to all of the people who’ve subscribed. Please reach out if you have thoughts, questions, or ideas for what I can write about. I’m all ears/eyes. And, I do love words a lot, so let it be known that there will always be a tl;dr at the very bottom of my posts and I won’t be (too) offended if you jump straight to that part.

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I think some of life’s best learnings come when we jump into new situations with open minds. It’s a big part of why I was so excited to leave management consulting, because I found it very constraining to always have an existing framework or approach for a problem when jumping into new cases. Early on in my time, I’d always wonder, “What if I have a good idea that doesn’t fit into the framework?” As I got more seasoned in the role, I realized that I started to only think within the bounds of that box. It made me very efficient – I was good at problem solving quickly and running with minimal context, but it also made it hard to be creative and I always played in a “safe” band of options and ideas. It’s rare to hear a management consultant talk about an absolutely groundbreaking or risky project because of the way problems are approached.

When I got to TestBox, I’d never worked a day outside of professional services.

(If anyone from work is reading this, I know this is a real shocker, right? 🙄 For all the others, there’s an ongoing joke at work about how I can sometimes be too consultant-y. Early on, I often got called out for saying “Back at Bain, we would do this…”)

My first internship was in credit rating, which is a pretty traditional and risk averse space (duh). My second was in investment banking and my third was in management consulting. When I started at TestBox, you can only begin to imagine how excited I was to work on a MacBook, be allowed to wear leggings, and…take arbitrary breaks in the middle of the work day without being attached to my phone / Slack / Teams / whatever. (Fun fact: I have Slack notifications muted on my phone permanently and instead tell everyone who works closely with me to text if I’m offline when there’s something urgent/I’m a blocker.)

Since the start of my career, I’ve been a big fan of the advice to follow the people, not the work.

This is why I joined TestBox. TestBox is cofounded by Sam, one of my former managers from Bain, whom I had apparently promised to follow. (There’s a card that I penned in 2018 that said “I hope you come up with a great startup idea…I’ll be there!” which I have zero recollection ever writing, but it is actually my handwriting.) 

When I “interviewed” Sam about my role at TestBox, Sam told me it would probably be a bit of everything and would likely be whatever we were missing the most at each point in time. I asked him if he had a title in mind, and his answer was that I should figure one out for myself. This little exchange captures a lot of how startup life has been so far for the last two years. I landed on Chief of Staff as my title, because it seemed fitting for a job I couldn’t quite describe. Over the past two years, I’ve rotated through a number of roles on the team and owned a rotation of responsibilities. 

The things that I have done since day one that I continue to do include:

• Running our team wide meetings (most notably All Hands)

• Leading our annual goal setting and planning process

• Championing our team fun events and onsites (in the early days I did the planning myself though nowadays I work with our awesome committee to plan these)

• Steering the exec team on a number of culture and people-related topics

• Supporting different teams in cross-functional collaboration and on ad hoc efforts

The things that I have done at varying phases of the company’s history include:

• Being a stand-in product manager

• Running our partnerships program (from selling to new partners to managing the experience for existing partners)

• Spearheading a number of marketing experiments and running our community building efforts

• And, most recently, serving as our de facto user success/enablement team, by working with our newest users and monitoring our usage stats

It’s generally been the case that I take on an area of ownership for a few months before the efforts scale and require the next level of maturation from someone who has actual experience doing the job. At that point, we hire a full time experienced person to take over the efforts and polish them to the next level. I’ll usually spend a lot of time with our new hires early on transferring knowledge and giving them context on what we have or haven’t tried and where we’re succeeded vs struggled.

I always read job descriptions for Chief of Staff roles and wonder what it really means, and hope that the way I’ve laid it out here brings a bit of light to what the job can look like more concretely. 

Another tidbit that I often like to share with others is that the Chief of Staff role tends to be defined by the roles that are missing from the rest of the leadership team at a given company. Say, for example, you’re hired as a Chief of Staff at a startup before a marketer is hired, but there is a CFO and a CEO who was a former Product Manager. There’s a decent chance that you’ll wear a marketing hat for some period of time but unlikely you’ll need to take on any finance or product duties. If I’d been given this advice, I could have looked around TestBox in our early days and predicted that I’d probably rotate through quite a few hats before settling down into a more narrow role.

In January, my title officially changed.

After a series of conversations, Sam and I felt that I’d done my two year tour as Chief of Staff and it was time to focus my role a bit more. A large impetus for the conversations was that we’d finally hired someone for each functional group at TestBox and it wasn’t likely that I’d be rotating through different functional areas in the near future. I was finally going to have some time to step back and focus on strategy for TestBox overall, and alongside that, I could start taking over more of the ops pieces that were still on Sam’s plate, so he could shift his focus to more selling. 

Nowadays, as Director of Strategy & Operations, I’ve taken over a few additional responsibilities including managing all of TestBox’s finances, the budget, and our fundraising planning. I still rotate to support different teams or to tackle different strategy questions depending on top priorities and where we’re feeling stretched at any point in time. Most recently, I’ve been splitting my time between ops, acting as our success/enablement person, doing financial planning for the year, and leading analysis on our sales processes to pinpoint where we can be more efficient and collaborate across teams better. 

At the end of the day, I don’t think the title change has affected the work that I do a ton. I do think there is an appropriate title for each state of the company’s growth, and my current title reflects our current size and team composition better than Chief of Staff. It is definitely also easier to go into certain external conversations and introduce myself with an area of clear ownership vs being a generalist as Chief of Staff, though there are also times when I feel that being Chief of Staff has its unique advantages as well.

My general hypothesis – and what I’ve also heard from others – is that this won’t matter significantly until we either hire a new Chief of Staff or grow and I can build out a team for Strategy & Ops. At the end of the day, I still see my role as a hybrid of tangible ops pieces that are very much of the “keeping the company running” nature, which is my safe haven where I know an hour of work will yield an hour of progress, and a smorgasbord of more intangible work that really varies by the day, which is what keeps me on my toes and often has higher variance in success vs hitting roadblocks.

TL;DR

As Chief of Staff, I wore a lot of different hats. (I recommend perusing my bulleted list above.) Chief of Staff roles can sometimes be defined by whatever a given company is missing. As I’ve transitioned into Strategy & Ops, my scope has narrowed and become slightly less rotational. I’d love to hear from others who’ve held either role and see how your experiences stack up.