Chief of Staff: The Role, the Craft, the Community, with Scott Amenta

Alexis:

Hey Scott, can you tell us a bit more about you and your background?

Scott:

Hey, Alexis, great to chat with you today. I'm Scott, come from New York, currently living in Berlin. I've spent most of my career at early and growth-stage companies really working across a number of different fields like operations, business development, strategy, and even finance at times. I spent a good part of my career at companies going from five upwards to 500 employees, really operating in a generalist role, without any clear definition of what to call that.

It wasn't until around 2014 that I joined an early-stage e-commerce marketplace called Spring based in New York. At the time I was looking at chiefs of staff coming out of companies like LinkedIn and Google, and obviously hailing from the political space as well, and thought that there was a clear potential need for that same position within these early and growth-stage companies. So I started to carve out that position for myself at Spring. In 2016, I officially became the Chief of Staff there, after growing the company to around 80 employees in two fast years. Shortly after that, I started a Chief of Staff community titled Chief of Staff Network. I've continued to grow that community and learn a lot from the members that we have within it.

Alexis:

Thanks for sharing, Scott. What is a community builder?

Scott:

If you look at the history of communities online, really the first emergence of communities was on some of the major platforms like Facebook, Reddit, LinkedIn — these very large groups of people organizing around similar personal or professional interests, with potentially a lot to gain from one another, but without necessarily the same intimacy you might get from an online meetup, as an example.

The idea of a community builder is really a person that is willing to set aside the time to put those people together in interesting scenarios. Identifying common problems, common needs, common interests — whether they're personal or professional goals — and building the content, resources, platform, and infrastructure necessary to connect those people, bringing them together to solve and grow and learn.

Alexis:

I have a big bias on that. When we speak about community, my first thoughts are on open source communities. Do you think there's something to learn from open source communities in what you are doing?

Scott:

Absolutely. The nature of communities today has evolved in two different parallels. On one hand, you've got open source communities where people are free to join, free to self-identify with other members of the group. On the other side you're starting to see more of these private communities, some of which are free, some of which are potentially paid for. There can be value in getting a higher-end experience — not that the open source communities can't provide that, but a higher-end experience knowing that there is some gateway or wall that's identifying members before they come across that boundary to engage and interact with other people.

Alexis:

You mentioned that you started that community of Chief of Staff. What is special about the Chief of Staff role according to you?

Scott:

The Chief of Staff role obviously has been very prevalent in the political space for most of the history of America at least. It has only very recently emerged as an interesting position within early and growth-stage tech companies, albeit it has existed for a little bit longer at some of the larger tech organizations, Google and LinkedIn being the two most prominent.

What's so interesting about the position is that it's a highly ambiguous role. At every different company, for every different executive that hires a Chief of Staff, that Chief of Staff tends to have quite different responsibilities. What that leads to is a role where you have people from very diverse backgrounds coming into it. I meet chiefs of staff that come from marketing backgrounds, business development backgrounds like myself, strategy and finance backgrounds. They're entering into that position because it gives them, in some senses, unparalleled access to see the entire purview of what it takes to grow a company.

What that means is you can often have chiefs of staff that are, in some cases, earlier in their career, but operating at the highest levels of these organizations. That's probably one of the most interesting things about the role.

Alexis:

The exposure to a larger scope is definitely different for people. It's an interesting part of the role. Why your community for Chief of Staff?

Scott:

In looking at that ambiguity of the position, two things are immediately evident. One is that chiefs of staff need resources and support and an infrastructure layer with other chiefs of staff to help them grow and level up those skills to be able to excel at the position. At the moment, or at least when I was a Chief of Staff, there weren't any dedicated resources talking about the position, helping me identify the areas where I should be focused, helping me think about what my career path might be. It was immediately evident that at least somebody needed to start writing about this position and really sharing their own personal narrative and experiences to help the others entering into the same challenges.

The other side of the coin here is really education of the market. I was immediately aware of the Chief of Staff role being on my resume, knowing that I was going to have to take that narrative and describe my responsibilities and accomplishments as a Chief of Staff to another company with the potential of that company not understanding what a Chief of Staff role was. My belief is that it's not up to one individual to define and describe that role to an entire industry. It's really up to a community to do that. I felt that there was nothing better than taking a group of people that were in our role — with a lot of ambiguity — being able to define that experience together, and therefore educate the entire industry about what that role would mean and the strategic importance of it.

Alexis:

I really like that — community to support you so you can excel and grow. The role is sometimes the lonely role. You're working with your principal — the CEO or a high-level executive — and with the leadership team, but it's a little bit of a lonely position. So having a place to find support and the resources and the peers that will help you to excel and grow is where the community is really valuable. I didn't think about that part about educating the market, but based on the number of times I need to explain what a Chief of Staff is, I think it's a very good point.

Scott:

And to be fair, we're still a long way away from a world where everybody understands what a Chief of Staff is, and again, the strategic importance of it.

Alexis:

In the Chief of Staff role, I really think that building the leadership team around the principal is something important — and part of the responsibility of the Chief of Staff. Do you think it's part of that role?

Scott:

Yes, I certainly do. If you look at the Chief of Staff role and the reporting structure, a Chief of Staff doesn't tend to be an owner of any specific P&L within the organization. What that means is that they don't have ownership over any particular group or unit, and instead can focus on the holistic picture of the company. The organization needs to be designed around a principal, and the Chief of Staff is there to support that principal — making sure that other direct reports are getting the information, getting the resources, and getting the attention that they need from that principal. It really becomes this interoping layer so that the organization can run more smoothly, more effectively, without any individual bottleneck. And the principal tends to be that bottleneck sometimes.

Alexis:

Very good point. What does being a leader mean to you?

Scott:

I look at leadership in a few different contexts. The first thing that a great leader really does is creating a vision for the team — a vision and a mission that the team can really get behind, that they understand, and that they're motivated to work towards. The second core component is really, then, how do you build the team? How do you choose and pick the right players that vibe together well on a cultural level, but also have the tactical skills necessary to achieve that vision — so that every new person that you add to that team is not just an incremental add, but is an exponential add.

The third thing that drives a great leader is the ability to inspire. In order to create the motivation to go and achieve great things, to work on difficult challenges, you need to be able to inspire the people around you. That takes a lot of courage to stand up, give great examples, tell great stories, and make sure that people are really interested in the work that they're doing and have that dedication to the challenges that they're trying to solve.

Alexis:

Really difficult challenge. I love the way you are framing that. I particularly love the idea of exponential add, which means that you will need to look at a diverse team, not only adding skills with people that are similar.

Scott:

Exactly. Diversity means a lot to a team — diversity in experiences, diversity in terms of where that person is coming from and the types of problems that they've worked on before. I worked for an e-commerce company back in New York as a Chief of Staff. Very few of the people we hired were from the e-commerce world. They were from the retail world. That diversity led to the creation of some very unique product experiences for our consumers that were, in a lot of ways, fundamentally different than what the rest of the industry was doing at the time. That really speaks to the value of hiring a diverse set of candidates that can run the organization properly.

Alexis:

Excellent. What do you think are really the first steps when you build a leadership team?

Scott:

There are a few things to look for when building a proper leadership team. The first is really background and experience. That goes without saying — you want to make sure that the people you're hiring are equipped to do the job. Going back to the three points I made around leadership, they're able to bring those elements to the table to inspire not just their immediate reports but also the rest of the company. You have to imagine that any leader that you're hiring on the executive team can step in and essentially run the entire organization if they needed to. In the absence of the CEO, for example, could that person stand in front of the company and drive the same level of motivation and inspiration that the CEO may be doing every day?

The second piece really is around cultural fit. Does that person meld well with the way that the company was built from the beginning? The way that the employees have come to reflect their culture — do they prescribe to the values and mission that the company has, and what are the examples that they've demonstrated in their own careers?

The third element is really around work style. The way that they work, the way that they think about even work-life balance — does that also correspond to the way that the company has been operating? These things, in some cases, can be written in stone — things like culture or work style — and it can be very difficult to have one leader that is swimming against the grain of those things and trying to convince the rest of the team that it's okay. You really need a leader that sets examples, and ideally those examples are things that the company has already prescribed to.

Alexis:

Great summary. What do you look up to as a leader to learn from, to be inspired from, and of course, why?

Scott:

One person that I certainly look to as an inspiration for leadership, and certainly within the context of community building, is Alexis Ohanian, CEO of Reddit. His story is in a lot of ways fascinating — not just in the sense that he started a company, sold that company, left as CEO, and then later rejoined as CEO to lead it into its next chapter. Alexis has always been there as a person, really fostering — back to this idea of open source communities — the idea of connecting people, helping people foster relationships online that in other ways was very difficult to do. Reddit has always been a source and destination for great information, interesting people. You name the niche, it should probably exist on Reddit. Alexis Ohanian's vision is really behind that and he's championed that even from the early 2000s. I've got a lot of respect for what he's built there.

Alexis:

Very good one. What gives you energy? Where do you find your energy, and what drains your energy and maybe your tactics to avoid those energy drainers?

Scott:

The thing that gives me the most energy — and honestly, the reason I really enjoy this idea of community building — is the one-on-one relationships. I never really found myself as driven or as eager, even having worked at companies that have hundreds of thousands or millions of users, where those users ended up becoming numbers on a spreadsheet, numbers that we were looking at in terms of retention and conversion and growth, never really with that one-on-one personal touch.

What I've found with the idea of community building is, even with thousands of members, you still have a very personal relationship with each one of those people. They may not be your best friend, but you know them almost by name, you know their backgrounds, you have conversations with them. What I've come to realize is that you can build substantial businesses that are built on top of communities and still retain that personal nature of the business.

Every time I get off the phone with a Chief of Staff, it's new reinvigorated energy to just keep doing it, to continue building resources, to continue fostering more relationships, to continue connecting people together. Seeing their successes is essentially my success. That's a really rewarding part of the experience.

Alexis:

So the other face of the coin is what drains your energy.

Scott:

Most recently, Zoom calls — but I think we're hopefully moving on from a world where everything is just virtual. The thing that drains my energy the most are, frankly, internal meetings — meetings that could otherwise have been solved by email, by Slack, by more asynchronous methods of communication that don't require 10-plus people in a room where the conversation never really comes to a conclusion. It just comes to more work and more to-do for everyone where the problem may never have needed to be solved in the first place. I'm lucky now to be working as a co-founder of a company and can really set the cadence and way that the company operates around that internal communication style. But it's certainly not something I missed working for some of the larger companies I've worked with that just have way too many internal meetings and never enough time to do actual work.

Alexis:

That's a good one. I like your tactics to avoid those. There's a lot that can be achieved with asynchronous communication with the tools that we have today. Sometimes a shared document is much better than trying to define a problem statement with 10 people in the room.

Scott:

And in some ways this is the benefit of having a Chief of Staff: they can really be there to help figure out what that cadence is for companies that have, in some ways, lost their direction when it comes to too many internal meetings. Certainly something I've done as a Chief of Staff is really review every team's internal cadence and do a deep dive on the importance of each one of those meetings — and scratch them if they're not necessary.

Alexis:

Really good advice. What would be the first things you would recommend to people who want to improve their skills in whatever their domain is?

Scott:

The first thing that I would recommend is to try to identify a mentor for yourself. That mentor can be someone that works at your company that maybe is not on your direct team but someone that you look up to as a leader. It can be someone external to the company — maybe someone you've met through former classmates or former colleagues. Having that person — not necessarily a professional coach, although that's equally important, but a mentor or person you can ask deep questions of about your career, ask questions that are more tactical focused on some of your day-to-day challenges, with unabashed advice — is super critical to being able to get that real-time feedback and that confidence to take the next steps in your career. Those are the things that have probably helped me the most as I look back over the last 15 years.

Alexis:

Very important part. Are there any resources you would want to recommend to people?

Scott:

From a resourcing perspective, the most obvious thing to say is — well, there's probably a community out there waiting for you. The best thing to do is to go out and look for the online communities that are available to you, again based on your personal and professional interests. I've seen communities in basically every industry at this point. If there's a niche that you're interested in, it probably exists in one way or another, and those people are there waiting for you. You'll be surprised at how many people share those same passions as you and are going through some of the same challenges, and are willing to help.

Alexis:

That was, of course, the answer that you would provide, but you're absolutely right. I like what you're saying — think about any niche that exists, there's probably a community waiting for you. You are not alone. We have the opportunity to reach out to those people. This is very cool, very inspiring. Thank you Scott for having joined the podcast today.

Scott:

Thank you, Alexis. It was a pleasure. I really appreciate it.

Alexis:

Thank you for listening to this episode of Le Podcast. Go to blog-alexis.monville.com for the references mentioned in the episode and to find more help to increase your impact and satisfaction at work. Drop a comment or an email with your feedback, or just to say hello. Until next time, to find better ways of changing your team.