Introduction
Bea [00:06]
Welcome to Top of the Ops, the podcast where we have real conversations about what happens behind the scenes of startups. I'm Bea, former VC at Lakestar, now Chief of Staff at Praktika.
Ceci [00:16]
And I'm Cecilia, former VC at Talis Capital and now FD at PortalOne. We both made the jump from VC to operator a couple of years ago. And now, when we tell our friends we're a Chief of Staff, they sort of nod politely and have no idea what we do.
Bea [00:31]
My parents don't know what I do, and it's been six years now. And when you try to explain where you're going after it, it just gets murkier. Full confusion.
Two Thirds Promoted, Two-Year Tenure
Ceci [00:41]
We're coming full circle. We started off understanding why we made the jump, and now we're trying to understand what next jump we're going to make, or have made already. And two thirds of Chiefs of Staff actually get promoted after the role.
Bea [00:57]
That sounds great.
Ceci [00:58]
But the average tenure is two years, which means if you're in your third year as Chief of Staff, you have to ask yourself some questions about why you're still there.
Bea [01:09]
The third year, you got stuck.
Ceci [01:12]
Exactly. So today we're going to try to figure out what happens after, which third we're in, and whether we can figure it out. And probably even give some ideas of options, because as we said in our last episode, this is a fairly new role, and it's not one that has a very clear progression laid out right in front of you. So I think you need to get creative.
Bea [01:34]
So we're going to get creative today. That's kind of creative.
Do You Worry About What Comes Next?
Ceci [01:39]
Bea, starting with you. Real talk: do you worry about what happens after Chief of Staff? And if I know you the slightest...
Bea [01:44]
I have to have everything planned, started three years before. Yeah, it's hard. I came from VC, where everything was a very clear career path: one year as analyst, two years as associate, three years as principal, and then you have to get promoted to partner in the third year. And before that I did banking, where it was like three years as analyst, three years as associate, and everything is so well defined. And now I'm in Chief of Staff and I'm like, no idea what's going to come next. No idea what the timeline is.
Ceci [02:13]
I think by now we've kind of figured out the timeline. The timeline is two years, but my two years are coming up, so we'll see what happens then.
Bea [02:26]
I think it's really murky, especially because you join a company and you're trying to look at what your options are after a Chief of Staff. And let's be real: either you join a company really early on and you try to carve a path towards a function, but you need to be quite early and really, really good to then progress up the career ladder of that function. Or you try to stay in these generalist roles but progress from a title point of view. The classic road that people talk about is the Chief of Staff to COO. But then a lot of people try to hire COOs who have been COOs for ten or twenty years.
Transferable Skills or Glorified EA?
Ceci [03:17]
I would go with a decision path, a decision tree. So I think the first crossroad is: are we building transferable skills, or becoming very, very efficient, glorified executive assistants? I would say that's the first point to analyse. What do you think?
Bea [03:32]
I hope it's yes.
Ceci [03:34]
Absolutely, yes, we are building transferable skills. However, they are way harder to showcase than in traditional, specific functions. If you started in sales, it's really easy to say, I've been doing SMB, hitting this much of my quota, and then progress, progress, progress. Whereas for us, the skills are murkier. But at the same time, it really depends on how you approach the role day to day. You can really own outcomes, drive strategic decisions and build general management skills, which is one of the various types of skills. And within the role you get exposure to P&L, to fundraising and investors, board prep, cross-functional execution, investor relations, projects that can really change the trajectory of a company. Cross-functional things that nobody does, and you're involved in them. What can be more transferable than that? You're a generalist who can jump in and out of anything.
Bea [04:39]
I would say then we're making the case. Yes, it's a launching pad.
Why Series A Is the Best Time to Join
Ceci [04:46]
Top of my mind, if you join the company as early as possible, you get exposed to more generalist things, so you probably have more options. Versus if you join at Series B or C, there will probably already be some functions filled. So your options kind of shrink, which is why, in my opinion, Series A is the best time to hire a Chief of Staff and get into the company.
Bea [05:07]
And something else that can happen is you join early on and start leading marketing, for example, because nobody else is leading marketing. Then the company grows and of course they want to hire a CMO, a seasoned executive for that function. However, you come with the backlog of knowledge, whatever you've learned about the company. So that lets you strategically position yourself just underneath that person, and it gives you a massive head start compared to other people in the department, if that's what you want to do. And that only happens because you started early on.
The Exit Paths: Finance, COO, Automation
Bea [05:44]
In my mind, it's probably a very good launching pad for finance director. We'll explore this further in your case. VP of operations, slash COO. So let's say finance path, pure operations path. In my case, I'm heading up the customer support team. Let's say I wanted to become head of customer support. That would probably be something I could do. Maybe not in my realm of options that I would love, but it's also something. Let's also consider a chief of automation officer. I think we're going to see this role popping up over and over again.
Ceci [06:27]
More than that, actually. As the company grows, you can become Chief of Staff but for specific functions and department areas. So for example, if you're a technical person, you can be across product and tech ops and R&D ops. Or business operations or rev ops, or go more into GTM, but with that function-area-minded expertise, which then lets you really progress forward.
Bea [06:58]
Absolutely. And if the company progresses, maybe you're post-Series B and you need a head of strategy, or head of biz ops, or business development. Anything on that front.
Ceci [07:10]
We're finding so many options. I haven't even thought about this myself.
Bea [07:13]
Also, the data backs it up. McKinsey found that Chiefs of Staff move up more than one level after the role on average. So you go in basically as a senior manager with no reports, and you come out as a VP or higher.
Ceci [07:31]
Exactly. And you're the first person who understands the needs of the business. You can actually foresee them, and then you can structure and position yourself to change direction laterally and go fill those gaps.
Bea [07:43]
So this is how you'd practically go about it. An example for me: I wanted some exposure to marketing. We were letting go of our VP of marketing, and it was going to take us at least a quarter to hire someone else. So I just put my hand up and led the marketing team for a quarter, because somebody needed to do it. And then I discovered marketing wasn't for me, but I was still very relevant to the incoming VP of marketing because I came with the backlog of knowledge. And if I'd wanted to, I could have become a much more strategic partner to that person, or to GTM. So you just have to see things.
Moving Up Internally vs Externally
Ceci [08:22]
Also, these are internal to the company. You can go external and do it as a lateral hire: go into another startup and make the jump. And I guess it also depends whether your company is growing fast enough for you to actually progress internally, and whether the CEO is going to let you go or is really stuck with you.
Bea [08:45]
But I guess you're the best person to explain what happens, because you've progressed past it. You're now FD at PortalOne. So how was that process for you, both internally and externally, and does it work better to move laterally, in your opinion?
Ceci [08:56]
Okay, so there are pros and cons with everything. I did it externally, mostly by choice, mostly because I just felt like a change. But I do believe the internal lateral move is slightly more difficult than the external route. That's because people have seen you as the Chief of Staff, and they won't be able to decouple you from the CEO as quickly as you'd want, just because your title changed. And also, before, you were the person leading a lot of ownerless tasks, and unless you found somebody else to do them, you're probably going to have to do your new role and that old role. So it's really important, if that happens, to establish really clear boundaries. And it's not always easy. The external route is easier because you're starting at a new company with a clean slate. What you've done in the past and the experience you've gathered is something you bring as an addition to your role. And there's a lot less ambiguity about who you are and what you do.
Staying in Your Lane
Ceci [10:05]
One thing I want to mention, though: when you change role to something more function-specific, you still have your old habits of wanting to fix everything, because that's what we used to do. I'm telling this to myself one month into the job: try to understand what is yours to fix because of your new role, and what is not yours to fix.
Bea [10:25]
Do you manage to stay in your lane? As in, as finance director, you're just, this is my job, I won't try to fix things here and there. How much do you think you're still doing it? Just give me a percentage.
Ceci [10:40]
I'm still doing it, maybe like 20 to 30 percent. There are two components. One, I have an aversion to things that are unfixed. And the second is, I think when you choose to work for a startup, you choose to work somewhere you can't just point other people at things, because there's not always going to be somebody who owns something, especially if the company is young. So we all have to roll up our sleeves and do things that need to be done, even if they're not part of your job. But if that stays within 20 or 30 percent, that's fine. If it goes to 60 percent, that's a problem.
The Dead End: Becoming Obsolete
Bea [11:19]
Exactly. We made the case for the launching pad. We can also make the case for the dead end. I actually spoke with one person at the start of my Chief of Staff journey who had been a Chief of Staff and then progressed to COO. What this person told me is that they did exactly the Chief of Staff role: they figured shit out, they hired a person for it, then they figured the next thing out and hired somebody for it. So this person progressed. They were COO, they had people reporting to them, maybe a head of HR, a head of ops and the finance director. And then this person was just a useless link between all these people and the CEO. They ended up kind of firing themselves, because they became obsolete and didn't have vertical specialisation in anything. Because you're so generalist, I think at some point you have to decide what you're going to actually specialise in, otherwise you risk hiring people and becoming irrelevant for the company.
When to Go Deep, and How Deep
Ceci [12:23]
That's a big fear. A question I'd like to discuss: when is the time to go deeper, and how deep would you go? I'll use my own experience. I would always want to hold finance. I think it puts you at the centre of what's happening in the company, because everything comes down to certain metrics and numbers. And maybe not really the accounting side, I have no passion for that, but at least the FP&A side. I think it's really important, and it puts you in a very strategic position to discuss what the plan was and what the plan is. If I go down that route, maybe I'd want somebody to help me out, like a finance manager, but I'd always want to hold deep expertise in that function. And everything else, you can hire somebody. I don't feel a particular affinity with HR, for example. I like it, but I don't think it's my calling. I don't feel a particular affinity with customer support either. I think it's a good operations thing to hold, but I'm fine with somebody else leading it. So that's probably what I'd pick. But it's also specific to Praktika, for example. It's not a rocket-science model: we have consumer subscriptions, you don't need that experienced CFO who's done it over and over, because we literally have three product metrics. So that's probably my experience. How about you?
Bea [13:47]
I agree with you on finance. If I'd told Cecilia ten years ago, you're going to have FD as a title, that wouldn't have landed anywhere. But I think there are two types of finance. There's the accounting, just getting the numbers right, and there's the strategic. And this is why, for me, the CFO role and the COO role are sometimes blurring, because who you are is a partner to the CEO in terms of execution and strategy. And how you get to those roles, which is what a lot of people aim for, is really different. The COO path, for me, is a lot murkier, a little unclear. Whereas the CFO path is a bit more proven. So you can start getting that deeper domain knowledge in finance, which is what I chose to do. And then, if the opportunity arises to move to a COO-type title, you still have deep expertise in finance that differentiates you, as well as expertise in broader internal operations. So that's my thinking, but it's really not a traditional path. If you look at the constellation of C-level titles out there, it's quite limited, and I don't think it represents the growth opportunity for Chief of Staff very well. I think that's a result of this role, and these types of problems the Chief of Staff is solving, being fairly new. Perhaps we'll see more creative job titles in the future. I'd be here for it, but maybe not a chief entertainment officer or whatever.
Ceci [15:30]
It's interesting, because if I had to wrap what I do in a title, there isn't really a title available. At some point you just have to drop the expectation of having a title people would fully understand. Because if you explain it, people understand that at the end of the day the title doesn't bring all the value. Of course it's nice to have a good title, but it's also about what you actually do on a daily basis.
The CEO Dependency Risk
Bea [15:57]
Maybe going back to a question I have on how to progress. Your entire value proposition is tied to one person, the CEO. They're who gives you authority, responsibilities and legitimization. How much is that a risk? What happens if they leave, if they get fired, if the CEO just changes? How can you progress in your career without them? And is that a problem at all?
Ceci [16:20]
I would say your destiny is about 75 percent tied to the CEO, because that's the person you deal with on a daily basis. But for the rest of the percentage, you have to build your own credibility with the broader team as well. And you're always in touch with the broader team. But I'm not going to lie, it's a harsh question, because you are primarily tied to the CEO of the company.
Bea [16:56]
You can build dependency across other members of the leadership team too, but that doesn't always help, because it stretches you really thin. It's a double-edged sword. Either you end up stretching yourself really thin, or it actually becomes the way you progress laterally, and you start becoming whatever title we want to use for that other department, getting a bit more domain knowledge and progressing in your career.
Is There an Expiration Date?
Ceci [17:22]
Yeah, I agree. And I'm going to ask a question: do you think there's an expiration date on the Chief of Staff role? Should you start thinking about next steps?
Bea [17:31]
It really depends on what you want. There's actually scope for a career Chief of Staff. Somebody who jumps from company to company, finds a lot of joy in going in, doing something for a couple of years, seeing how things go, then moving on and using that knowledge as a transferable skill. I don't think there's anything wrong with that, if that's what you want to do. I think the longer you are a career Chief of Staff, the harder it becomes to break the ceiling and move up. So that's something I want to clarify. There is an expiration date, and it's two to three years within one company. If you're the Chief of Staff of the same CEO at the same company and you're entering year four, now that's a problem, because you're not learning anything new anymore. You're solving little bits of problems and just operating on knowledge you gathered before.
Ceci [18:30]
I also think, and this might be slightly controversial, if you have the calling to go into multiple startups from zero to one or one to five and keep fixing and doing the same processes, maybe the problem is you. Maybe you have an attitude to be the "crocerossina", I don't know how to say it in English, to be the fixer, to just be the helper. And at some point, don't you want to progress to something else? Apologies for being very blunt here, but maybe if you feel the calling over and over and over again, the problem is you.
Bea [19:11]
Maybe, yes. I do have a bit of that calling myself. I think there's something scarier about a large company, something that gets to 500 employees. Some executives just love the zero to one or zero to five and then keep doing that, because they love to feel the impact and be in a company where they know everybody's name. That's the comfort zone, not in terms of tasks, but environmental comfort zone. If you're used to working at a certain pace, breaking things and having a lot of freedom and authority, then progressing to an environment with a thousand people, so many layers of management, a bit more bureaucracy, it can feel really daunting. So I see it slightly differently, but that's because I'm a forever anarchist.
Ceci [20:06]
I must say, perhaps the type of companies is changing with the role of AI, because I can't see many companies becoming thousand-person organisations. Perhaps you can have a greater impact on revenue with a smaller team. So that period of agility and flexibility might stretch way past Series D, or even until IPO. Of course, if you IPO, you have to have certain structures internally. But I think that's changing too. There are new types of startups coming in, way less bureaucratic, way fewer people, where you can do whatever you want with AI. I think that's way more fun to progress in, past Series B, C and D.
Founder and VC as Next Steps
Bea [20:55]
We've also forgotten about probably one of the main areas of progression after Chief of Staff, which is founder.
Ceci [21:04]
I was about to say something else actually. VC.
Bea [21:13]
Okay, okay. So let's go. Let's go founder first. Not to name names, but I'm going to shout out Emilie Spire. She was originally OG VC, then a founder, then head of operations, and now she's back in VC. Shout out. Taking a bit of a founder break.
Ceci [21:35]
Okay, so what's the case for Chief of Staff to founder? We touched on it in our episode with Gaby, and I actually know one. Aurelia, ex-SpeedInvest, then Chief of Staff, now founder. I'm naming names here. Shout out to all the women. You're so generalist that you have a little bit of competence in every function, you're quick, you're fixing things, you're wearing multiple hats, and you work closely with the CEO, so you see what's happening on that side. I think it's very easy to make the jump and be tempted to do it yourself, with the deep knowledge and awareness of how hard it is. You're very conscious of it, so that might also be a deterrent. But I could see myself being a founder at some point, maybe later in life. I'm not sure if it'll be a VC-backed business or not, but with the competencies I've seen in a specific sector and business model, I think I could do it.
Bea [22:38]
I've been a founder before. No more for me. But I agree, I think a Chief of Staff would actually make such a great founder, in terms of execution and running a tight ship. Especially if they're working on something they're personally passionate about. When I was building something deeply technical that I knew nothing about, I could run a tight ship but I couldn't have the vision. So if you can merge those two areas, I think that works perfectly. What's the case for VC? Let me know.
Ceci [23:13]
All right, so you're great at working with founders, but also understanding founders, understanding when there are red flags or difficulties before they arrive, and building rapport. Number one, super important. Number two, you've literally been on the board, you've been part of those strategic conversations, so those aren't new to you, and you've seen them from the partner side too. Number three, you know how a company is run, the problems and the areas, and you have that instinct for seeing a problem before it arises and trying to be helpful enough to fix it. Now, as a VC you probably won't be able to jump on and actually fix it, but you can have the conversation sooner rather than later with the founder, you can suggest how to fix the problem, you can introduce people who can help. So you have those three things that can be really, really good.
Bea [24:19]
You're at the forefront, because you actually see a lot of software, especially at a company that experiments with new things, so you can spot trends early. You see patterns within the company and outside it. Your job is always to be thinking strategically. Obviously, talking about it right now, for me it's a bit different, because I had invested before. So the pattern recognition, seeing how the world works, being able to build rapport with whoever is building something, those are all qualities I had to work on before. So for me it's a little bit easier.
Ceci [24:55]
If you had to go back to VC, would you go back as an investment partner or as an operating partner?
Bea [25:00]
I don't know. Moment of silence, pause for reflection. We have to think about it. I don't know. Nobody else has asked me that question, and I can't answer right now.
BS Titles and Showing Progression
Bea [25:09]
But I actually have a question for you, because I sometimes see this role being like, okay, so you go from Chief of Staff to chief strategy officer or whatever. Are there some BS titles that are just used to create progression for a Chief of Staff, if that person couldn't be a COO, for example, or if you already have a CFO?
Ceci [25:34]
Like Chief Strategy Officer? Yes, yes, there are many bullshit titles. I think people need to feel progression, and society looks upon a title held for more than two years, unless you're C-level, like seven years as CMO, that's great, as a lack of progression, whereas in reality maybe your scope is changing. So you sometimes have to dress up your role with a different title just to show progression externally, because in most cases we might not retire from our current businesses, and we're going to have to find a job in the future. So yes, there are some BS titles that just show progression, but they're useful in the grand scheme of things.
Bea [26:15]
I think I'm here for BS titles, actually. Whenever I was talking with my old CEO, I came up with so many random titles I could have, just for fun, just to keep people on their toes about what I'm up to. I had Chief of Staff with a U. I had VP of BizOps, et cetera. I had ops, just random things. But nothing serious, because we're actually a more serious company.
Measuring Success Without a Function
Bea [26:51]
Well, after dissecting this topic, can we draw a line? Do you think Chief of Staff is a launching pad or a dead end? Which one of the two?
Ceci [27:00]
Launching pad, 100 percent, if you use it correctly, of course. If your tenure is two to two and a half years, by the end of year one or year one and a half you should try to position yourself for the next step. Understand if there's space within the company, maybe build more vertical knowledge in that sector, or if not, try to look around.
Bea [27:26]
And if you were to boil down what really determines your success in evolving past the Chief of Staff role: build trust with the CEO, but also the broader executive team, and spend time developing some vertical knowledge. I'd say those are the main ones. What do you think?
Ceci [27:46]
I'd say, first of all, try to figure out what gives you energy, first and foremost, and where you're interested. Second, focus on strategic outcomes rather than just operational projects from the beginning, so you show you're more than execution. And keep your eyes and ears open, because within a startup things change really fast, and you can be the first one to hear them and put yourself up to take on those challenges. Those can shape the trajectory of your career.
Bea [28:19]
Also, have conversations early on. I think there's nothing wrong with talking about it with your CEO. Like, how do you see my role progressing? What gives me more joy? And, wait, do you disagree with me? You're making a face.
Ceci [28:33]
I have a question to ask you about it. How do you measure success? How do you showcase success? And how do you benchmark yourself as a Chief of Staff, which perhaps doesn't even own a function? I have my own answer, but I want to know how you think about it.
Bea [28:48]
It's a bit hard, because you're typically doing non-revenue-generating functions. I have my Notion tracker with tasks, department, priority, impact. I'm just reading right now: priority, impact, status, type of task, delivery, but also outcomes and KPI next to it. So let's say you're working on a marketing project that's generated this many leads, and X leads converted into that. For finance, I'd say, I understood that these expenses were useless and we just cut them, so I generated this much in savings. Even just opening up a savings account that generated X amount of interest. Just try to put a number next to it. And I'm pretty sure there are certain things you cannot quantify, like preparing a Series B data room, but that has an impact implicitly. You can't maybe put it into numbers, but if you end up fundraising, that's probably a certain percentage of that fundraise.
Ceci [29:47]
The way I looked at it personally was: list the problems I solved for you or for the company, list the things that are now working better, and that's the impact. And then new systems, new processes, whatever I was building. As a Chief of Staff, I wasn't owning as much of a function. I was owning biz ops, and the outcome of that was quite clear: we built this, we built that, and this is how other departments are using it. But for me it was very much, showcase the impact, solve some problems, create new processes or redo things in a better way.
Bea [30:17]
I never had to properly do that, because I worked so closely with the CEO that I just have to remind myself first what I worked on in a year or half a year, whenever we did performance reviews. But I think I need to start taking notes now.
Ceci [30:34]
Also, did your trajectory vision change from when you started in your first Chief of Staff role to right now?
Bea [30:44]
It changed a lot. I always knew finance was something I was dealing with, but when I first joined, I wasn't sure. Maybe I wanted to get closer to product, closer to marketing and sales. And then, as you're in the role, you start finding what gives you energy and what you enjoy doing. For me it was a mixture of GTM types of ops for a B2B company, mostly, and the more strategic or finance side. I felt that was the most interesting. So that changed a lot. How about you? Now you've been two years into the job, how has the way you look at progression changed so far?
Ceci [31:28]
I think sometimes I tend to be quite stubborn. I go into something with a plan already, and I'm not very flexible with changes to that plan. Over the past year and a half, I understood that the important thing is what impact I make for the company. And then there's going to be a progression that happens. Whatever that progression is, it's probably not going to matter in the grand scheme of things about my daily job. My daily job has increased in scope and is still increasing, and I feel like I'm having more and more impact. As long as there's some recognition of progression, I think I'd be less strict on a specific path, because at the same time, some titles are just BS, and it's what you do on a daily basis that matters.
Bea [32:13]
I very much agree on job titles. We care about it just externally. Internally, they're just a tool to help us do our job better. Do you think CEOs need some education on career paths and opportunities for a Chief of Staff? The reason I'm asking: you hire a head of product, they do really well, they become a VP of product, they're amazing, they become a CPO. Very simple, the CEO knows that. But do they know the opportunities and how to use and help progress a Chief of Staff?
Ceci [32:52]
I think there should be a bit more education on that front, and it's something that's going to happen organically, because it's such a new role. In a traditional sense, like in American government, it's a role by itself, you don't really progress to a lot of things. But in the tech space it's completely different, and it's going to come with more people who progress to something else. So far the role has been around for four years, maybe more in the last two. And I can already see examples of people going to founder, recruiting for Chiefs of Staff, going into head of operations, going back to VC. So we just see more examples, and I think now it's becoming a bit clearer.
The Verdict: Launching Pad or Dead End
Bea [33:42]
So here's the answer. Chief of Staff is both a dead end and a launchpad, depending on how you, or your company's growth, or your CEO, is impacting it, and also whether you are deliberate about your exit strategy. And I am the biggest supporter of making your own destiny. I actually do not believe in manifesting, in waiting for things to happen. No, you have to go after it. And if you're in the right role, just ask yourself: am I building transferable skills? Does anybody besides the CEO actually value my job, or know what I'm doing? And what's my timeline to get out? If you don't have a good answer to those questions, you might just be drifting towards the dead end, and you have to check yourself.
Ceci [34:20]
And if you're thinking about taking a Chief of Staff role, I really encourage you to go in with your eyes open and think, this is an opportunity, an accelerator for me to do something else. But it's also an opportunity to learn where you're drifting towards, and what might be there for you to go and get. Those opportunities are most often not clear cut and not super straightforward, but you need to be the person in charge of understanding, looking at the opportunity, and making a job for yourself, whether within your company or outside it. It's something that should always be in the back of your mind. Three months in, one year in: okay, what should I be looking at? What is there for me to go and do and learn, so I can be ready for the next stage and the job I want?
Bea [35:17]
The uncomfortable truth is that yes, in most cases, Chief of Staff has an expiration date. And if you don't respect that expiration date, it stops being a launching pad and starts being a trap. I hope this podcast, where we've tried to be as creative as possible about what the options are, has given some inspiration. Maybe someone thinks, I didn't consider that path, maybe I should. And if there's a path we haven't considered in this episode, do let us know.
Ceci [35:40]
Please let us know. I'm very eager to understand more options, or more BS titles we should be using but don't know about. Thank you so much for listening to our whole series. This is the last episode. There might be a guest episode after, but this is our last solo episode. I should cry.
Bea [35:57]
We may be back. Maybe. Thank you for listening.