What is a Chief of Staff?

A year ago, I didn’t actually know what a Chief of Staff was. Now that I am in the role, it’s clear that it wasn’t just me - to lots of people it remains a mysterious and misunderstood position. I’m fast approaching a year at Kinde, so keen to shed some light on what I do, how I got here and what my biggest learnings have been so far.

You might have heard of the Chief of Staff role in the context of the White House - it originated in the military and government to describe the right-hand person to the President or other key leaders. These days, it’s becoming more common in startups and tech companies.

The role itself varies from company to company based on industry, size and stage but I would say most Chiefs of Staff are:

• An extension of the CEO or principal. Working very closely with this person as a trusted advisor, understanding the way they think and act and stepping in as their delegate as required.
• A force multiplier. Amplifying the impact of their principal by taking pieces off their hands so they can focus on the highest value tasks. Two minds are better than one!
• Not an EA. An EA is there to manage the time and day-to-day logistics of their principal. A Chief of Staff does not do that.

The reasons change based on the size of the company.

For an early stage startup, having a generalist hire early on can help to plug holes, execute on tactical pieces and grow the team. It’s also a great way to bring new skills to the founding team. At Kinde - Dave and Ev are engineers and Ross’ background is in design, so my strategy, operations and finance experience was complementary to their skills. Even when it was just the four of us, we were able to cover a lot of ground.

At a later stage company, the Chief of Staff will act as an extension of their principal - an extra set of ears and eyes to keep the company moving forward.

I started my career at a Big 4 bank, a natural first step from a commerce degree. I did a hardcore finance role and completed my Chartered Accounting qualification. I realised pretty quickly that wasn’t for me and moved into the corporate strategy team.

In 2020, I had a covid-life crisis. I knew banking wasn’t for me long term and decided to do something about it. I left and spent a year upskilling and working on projects that meant something to me.* During that time, I heard about the Startmate Women’s Fellowship - a program connecting women with corporate careers into the world of startups - and jumped at the opportunity to join. Through that, I was introduced to Ross.

For anyone that has met Ross, you know that a 10 minute conversation is all you need to be completely captivated by him and the vision for Kinde. I left our conversation so energised and excited. A few days later, I met with Dave and Ev and signed on the next day as employee number one and Chief of Staff.

* There’s a much longer version of this story but I’ll save that for another day.

At the moment, I think of my role in four parts:

• Strategic partner to the co-founders. I’m part of leadership discussions, board meetings and calls with advisors. I work very closely with all three co-founders but I spend a lot of time with Ross on all things business building.
• Team operational efficiency. Making sure we’re optimising our time as a team - having just the right people in essential meetings to keep things moving forward. This also means I help Ross to optimise his own time - taking things off his plate so he can focus on the highest value, highest priority pieces.
• Internal and investor comms. Putting together board decks and minutes, our monthly shareholder letter and organising the agenda and materials for our weekly team All Hands.
• Special projects. This sounds pretty mysterious but essentially it’s anything that doesn’t currently have a home. At the start, it was just about everything that wasn’t product (people and culture, finance, legal, early marketing) but now it’s more of the overarching projects like pricing our product.

The fun part about my role is it is constantly evolving. Sometimes I am spending most of my time on just one of these buckets and other times I’m spread across them all. There’s also no saying what my role will look like in 3 months time - and I love that.

There definitely isn’t just one perfect background for a Chief of Staff. I’d say it’s more about the type of person you are, rather than the experiences you’ve had. A Chief of Staff needs to be:

• Comfortable in chaos and willing to embrace ambiguity. Things change, a lot. Particularly at an early stage startup. You have to be level headed and keep driving forward.
• Communicative and clear. A sounding board but not a mirror. There’s no benefit in having people who think and act exactly the same so you need to be happy and comfortable providing alternate views and advice.
• A generalist but with some core foundational skills. It doesn’t necessarily matter what those skills are, but it helps to have something to lean into. For me, it was my finance and commercial law background that helped me hit the ground running at Kinde - helping to close out our funding round, building our financial models and setting up key processes.
• A sponge for information with a problem solving mindset. A chief of staff is usually spread across every team in the business. This means there’s a lot of information to take in and a lot of context switching. A lot of the time, you might be facing problems for the first time or being asked questions you have never considered before. Soaking up and retaining information, connecting the dots and proactively pushing for solutions is critical.

Aside from my product learning curve (which has been steep!) I’ve learned a few things about being a Chief of Staff:

• You spend a lot of time with your principal. This one might be obvious but it’s a closer relationship than you might think. You’ll spend time sharing thoughts, concerns and questions and often just chatting, so you have to make sure it’s someone you really like and trust.
• You have to get comfortable with taking action and relying on the 80/20 rule. Depending on where you’ve come from, this might be challenging, particularly if you’ve been anywhere near consulting or corporate strategy. Experiment, act fast and if it doesn’t work, try something else.
• It can be quite an isolating role. You’re likely going to be the only Chief of Staff at your company and you don’t have a natural ‘team’ like others do. You’re the only one doing what you’re doing. I’ve found it really valuable to build a network of Chiefs of Staff at other startups to share thoughts and advice on the similar challenges we all face!

As I said, until fairly recently, I didn’t know the Chief of Staff role existed but now I can’t think of any role I would rather have. I love the variety, autonomy, exposure and constant challenge and I’m excited to see how my role will evolve as we continue to grow.