What it means to be the Chief of Staff at an A16Z start-up

Toronto. Home of 500px. Photo cred: Jeff Shin (500px.com/photo/62334209)

Nine months ago I joined 500px, a Toronto-based start-up, as Chief of Staff to the CEO. The role was presented to me with a few disclaimers; it would be a high-intensity job, would require excellent organizational skills and needed a ‘get it done no matter what’ mentality. I had just finished three years in Investment Banking, it was my first job out of university, and I was not going to be deterred by the challenge. I did my fair share of Googling because at that point, my picture of a Chief of Staff had been painted predominantly by White House TV dramas (read: Scandal, House of Cards) and I was fairly certain the CEO wouldn’t require me to dispose of any bodies in the desert or cover-up illicit affairs. After looking through articles and blog posts not unlike this one, it became apparent to me that the Chief of Staff (‘CoS’) role does not have just one standard definition. Some skills and tasks are consistent, but the roles and responsibilities of the CoS depend almost entirely on the specific needs of the leader they support. Despite my uncertain future, I was inspired by the CEO’s vision for 500px and wanted nothing more than to work for him; so, I tentatively took the plunge and accepted the job with only the slightest idea about the adventure I would embark on. Nine months in, serving as CoS has been one of the most mentally stimulating, challenging and fulfilling learning experiences of my life. Disclaimer: This role is not for everyone, but if you’re even slightly intrigued and are looking for a unique opportunity, here are the highlights that they don’t share in any CoS job description:

The Struggles

1. Determine how to spend your time

After having discussed the job with people in the same role at different organizations, I learned that a consistent challenge across the board is determining how to best allocate your time to ensure that you add the most value to your team and company. At a fast-paced, growing start-up like 500px, there are a million interesting and all-consuming things going on at the same time across the business. It can be a challenge to prioritize and go where you are most needed at that exact moment!

2. Striking the balance between contributing vs. just doing it yourself

A significant challenge in my first few months was to strike a balance between providing the right amount of insight and analysis to help guide the decision making without taking over the task at its entirety. This allows the owner of the initiative to come to their own recommendation. As CoS, my role is often to contribute, not necessarily do.

3. Defining your role

Because CoS is a less well-known position within many organizations, it is crucial to lay out what the role is and what it is not. Without defining the role to the team, one can easily begin to drown in requests, meeting invitations and analysis/research that doesn’t fall under the umbrella of the role. Without clarifying your role and responsibilities to the people around you it can be difficult to allocate the necessary time needed to perform the tasks where you can contribute most effectively.

4. Learning how to work with the person you support

The first few months as a CoS is an exercise in over-communication and learning about the person you support. By definition, the people who hire a CoS are executives who are so busy that they need one, so it can be difficult (and frustrating) to find the time to get to know each other. However, it is crucial to understand how the other person thinks and works in order to work together efficiently and effectively. There can be growing pains here and there but the time spent up-front will come back to you both in spades down the line.

The Learnings

1. How to form and voice an opinion

I was initially hesitant to voice an opinion in the already intimidating Executive Staff meetings into which I was thrown. I was asked to vote on every decision and explain my reasons. At first, every opinion I offered was qualified with “I don’t really know anything about this but….” and closed off with “but I am probably missing something”. I often was (missing something), but I have come to understand and appreciate that in business as in life, one rarely has perfect information. In my opinion, nothing is more detrimental to a business than a lack of debate and discussion fostered in unique opinion.

2. The value of candid discourse

The fast-paced environment of a high-growth startup does not answer kindly to watered-down double speak, intended to spare feelings and above all else ‘not-offend’. Our CEO is a firm believer in radical candour and though I must admit I was initially thrown by his deadpanned honesty, I’m now converted. As CoS, I have learned that I am of limited value to the CEO if I do not communicate opinions candidly, confront issues directly and embrace conflict in discussion.

3. The utmost importance of communication and team work

During Week 1 as CoS, my new boss explained to me what he wanted most: make sure he kept his finger on the pulse of the company. Despite a fleet of tools implemented to encourage communication within the company, it remains a constant struggle to keep everyone apprised of all the moving parts as we grow (and continue to grow) so quickly. This aspect of my role has boiled down to judgement. Understanding if and when the CEO needs to be brought into a decision making process and what issues and changes he needs to be aware of, is a constant learning process.

4. Decision making

On my first day on the job, the CEO granted me the authority to act as his proxy and make decisions in his place. I was granted unbridled exposure to the tactical and strategic decision-making process of the executives. My role is to act as a CEO multiplier — I am to take decision making 90% of the way, freeing him up to make the last and most crucial 10% of decisions.

So What’s Next?

Another unique element of the Chief of Staff position is that it is temporary. Generally, the tenure of a CoS in tech is limited to 1–2 years. Over a third of the way through my time as the Chief of Staff at 500px, I am already starting to think about what will be next for me. Because the role gives you the chance to get your hands dirty in so many areas within an organization, it prepares you for a wide variety of opportunities. After matriculating from the CoS role, people often go on to run a business unit, become a functional lead, or do an MBA. This is another reason why I believe the opportunity to take on the role of CoS is one that any young professional should jump at.

Nine months into the CoS role, there are no dead bodies or cover ups, but rather a tremendous amount of learnings with a ton left to do in a very fast changing, fast-paced life of a start-up. I could never have imagined what the CoS of role would entail and that being said, no two Chief of Staff roles are alike — so this is by no means the playbook. In fact, the job is defined by the person to whom you report; therefore, my biggest piece of advice — pick a boss, not a job. The job is a difficult one to perfect and there is still no shortage of course-correction happening but it is incredible to have the chance to learn directly from my CEO. I continue to be given new and challenging projects every week, and am continually impressed by how much more I still have to learn.




Chief of Staff at 500px

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Emma Ainley

Emma Ainley

Chief of Staff at 500px

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