The VC Chief of Staff: Building in Ambiguity with Stephania Greco
36m 41s
Stephanie Agreco’s journey to Chief of Staff at Bicycle Capital is unconventional, beginning in Venezuela where she studied journalism to advocate for her country during a political crisis. After the media was shut down and her family’s oil business was expropriated, she moved to Miami in 2009, juggling jobs as a waitress, fitness instructor, model, and retail worker to build a new life. She later earned a degree in public relations and landed at SoftBank as an executive assistant for the Latin American Fund, where she helped managing partners build a team of 70 and oversaw strategic responsibilities beyond traditional EA duties. Despite the role’s ambiguity, she embraced it, leaving SoftBank to co-found Bicycle Capital from scratch, defining her own Chief of Staff position without a job description. At the VC fund, with a small team of six, she focused on operations—setting up systems, platforms, and partner networks—before evolving into more strategic work like investor relations, fundraising, and creating an ESG department. Unlike Chief of Staff roles at startups, her work emphasizes supporting investment and fundraising teams, connecting organizational gaps, and proposing initiatives. She views ambiguity as a powerful tool for creating value, allowing her to question the status quo, identify blind spots, and embed her problem-solving DNA into the company’s growth.
[Music] Hey everyone, welcome back. I'm Scott Amenta, founder of the Chief of Staff Network. So today I'm sitting down with someone who's path to Chief of Staff is genuinely unlike anyone I've spoken with before. Stephanie Agreco is Chief of Staff at Bicycle Capital, which is a growth stage venture fund investing in Latin America. And what makes this conversation so interesting to me is that we don't talk to many Chiefs of Staff operating inside VC firms. It's a rare version of the role and it's still being defined in real time. On top of that, Stephanie's story starts in Venezuela, winds through journalism, modeling, retail, fitness instruction, and eventually lending her as an EA at SoftBank before she goes on to help build bicycle capital from the ground up. Today we get into what it actually means to be a Chief of Staff at a fund versus a startup. And how she thinks about ambiguity, delegation, and scaling herself, and some genuinely memorable frameworks for anyone in the role. All right, let's get into it. All right, Stephanie, welcome to the podcast. Nice to have you here. Thank you for inviting me. This is a great opportunity. I'm excited for this conversation because we don't talk to very many Chiefs of Staff working for venture capital firms. And it's obviously a growing position, but I'm excited to kind of dive into this with you today and learn a little bit more about your path to venture capital. And what it means to be a Chief of Staff inside for your, in your case, bicycle capital. I'm sure we'll cover lots of territory along the way. It's a new role you can say for the venture capital industry and it's still being defined. So it's very exciting to talk about it because it helps me realize how much time has passed, how much the role and the company has grown. Hopefully, it helps other people that are in my industry as well. I'm sure you've learned a lot along the way. If I've learned anything having chatted with hundreds of Chiefs of Staff at this point, the role is always being defined and redefined and that's the part of the beauty of this position. So maybe together we'll come up with a bit of a definition for what is Chief of Staff being in VC world today? Absolutely. Before we get into all that, I guess maybe just walk us through the path to bicycle capital. What were you doing before what drew you to a Chief of Staff role at a growth VC fund? That's a real interesting question when I think about what brought me here because it did start at a long time ago in my country, how my personality in order to be a Chief of Staff started to develop. Are you ready for your role? I'm from Venezuela. So I was born and raised in Venezuela. I have European parents and my past life for staff started that early in my life with my childhood, the experiences I went through, the way I was raised and helped me develop a lot of resilient personality, a problem solving mindset and like a more strategic way of thinking and looking for the gaps, how can I make this better? I mean, understand that I grew up in a country that the political and social crisis got really intensified and I chose a career base of that. Maybe it wasn't the right decision, but I decided to study journalism and I wanted to speak on behalf of my country, I wanted to defend that. I wanted to really be involved with the opposition media and as you know, the media got shut down so I'm like, I don't have a career now. So what am I going to do? So I did like some public relations internships and jobs like event production and entertainment related, but never what I really wanted to do. Then my family's business, who I helped them build that business since I was like 14, which is crazy, got expropriated by the government because it was oil in the oil industry and there's a huge industry in Venezuela as you know. And then the situation became increasingly dangerous also because of the Lincolncy. So I was forced to make a decision to either stay in Venezuela and keep fighting, you know, with the risk of something happening or moving somewhere else. So I moved, in 2009, I moved to Miami and I started something from scratch. I had to, you know, juggle between a lot of paths and responsibilities. You know, I needed a job to pay my bills. I can hear a loan at first and this is crazy, but I was at the same time, I waitress, I fitness instructor. I did some modeling when I was younger here and also I worked in retail. I was working as a sales representative at a polystore for men. So I just had to like develop that, like I said, resilience, resilience personality, solve problems, how to be strategic, like as an immigrant and making a new life and speaking a new language. Like working, for example, in BC, when English is not my first language, obviously, was a big challenge. There were terms that I didn't know how to do, like how to start like talking in professional English and not casual. So I had to sit down, you know, figure out what my status was going to be in the country. I went back to school. I got my second degree in public relations and somehow I landed at Softbank as executive assistant for the Latin American Fund when he just started. So he was a startup inside a huge organization and I helped the managing partners build a team of 70 people in Miami. That was a huge achievement. I was helping two managing partners each one handling a billion dollars to invest in Latin America. And I loved that I was having that impact to help that side of the continent and my country from a big company like that. So it wasn't only a job, it was actually a good social and economic impact that I was creating one way or another. What a story arc. You started trying to give back and invite for your country in a way that kind of befit your skill set, media and obviously unfortunately didn't work out. As you said, a path of real resilience, having to move to a new country, learn a new language, adapt to a new business, social profile, ecosystem, Swiss Army knife of tools, I mean retail, modeling, etc. Probably things that even if you're not relying on them directly, indirectly have impacted the way that you operating communicate today. When you worked with Softbank, you helped launch I think a $500 million plus fund. So what did those early days look like? Softbank was a big challenge and not because it was a startup because when you have a startup inside an organization that is a startup fund, you already have like all the departments feel like you have HR and you have office managers like they help you, they train you, they tell you what to do. So you're just building a team, but you have all the support from all those departments and compliance and this. So you don't have to think about onboarding HR and people and what we do from scratch, but you do have to think strategically in who you're hiring, responsibilities, what events are you attending, what founders you're meeting, what countries are profitable in Latin America. In Latin America, every country has a different political upside and downside and you have to analyze that into like a governance structure in order to know where to invest and where not to invest. But the fund was $5 billion and we had five managing partners, each one handling a billion. So I started helping one, then two and then during COVID, there was a huge layoff and I helped five managing partners. So that was a huge challenge. And this was in the executive consistent role, right? Yes. So much of the work that you're describing sounds pretty strategic and curious when was that shift of mindset for you of you know, if I take kind of maybe the traditional EA mindset, it's very much like what does my principle need today? What are the backup plans to make sure that their capacity is filled up to 100% right? And they're kind of maximizing the available time that they have to how do I double or triple that capacity as an amplifier to their work, which is more chief of staff a little bit more strategic. When did that shift happen for you? Either as softbank or onwards? It happened at Softbank. I felt like I had a lot of chief of staff responsibilities. We did hire a chief of staff at Softbank, where I was very confused, but what they were doing screen-ons with you, I never understood and never worked directly with them. But I knew that I could carry on that role and make it grow and they find and you know, depending on my personality and the industry and who I work with. So after four years at Softbank, I actually was going to leave the company and go somewhere else that you know, they offer me a chief of staff role and I decided not to do it because there was a huge initiative from another team. They wanted to create a new fund. So I left Softbank with a huge risk to create something for scratch. I mean, think about you have a secure role where you get paid well and you quit that role to go somewhere else where you don't know when you're going to get paid because there's not even a payroll platform, there's no entity, there's nothing. But because I believe in the people that we're carrying this along, I made a decision left Softbank and it took us a year to build an entire company. And when you stepped into that new role was your definition of your job description and the things that you were going to be working on, what's it different than what you're doing at Softbank? We were all defining our roles. We were at six people, you know, it wasn't a big deal. Yeah. What do you want this role to be? You weren't associated, you want to be a partner? Yeah, I'm going to be a partner. I am going to be a principal and I said, I'm going to be a chief of staff. I said that without knowing what it meant. But that's what I wanted to do. I'm like, I want to be a chief of staff, I want to do more. I don't want to be only on operations and only thinking about day to day basis. I actually want to like impact the system and improve it. And I think it can do that, you know, based on my experience and my skills.
and how I know my personality revolves, you know? So I left SoftBank, created a bicycle capital with the team. I said, "Chifu staff, at the time, I was very confused. I thought, you know, the Chifu staff will look different depending on industry and define in this role dependent on me more than anyone else. I didn't have, you know, a job description obviously, so I created it myself." And all I did was take a state back and just, you know, what do we need, formation documents? Now we need to be on the backup office. Do we want to hire departments or do we want to create a system of platforms and partners, consultants to work, save that money on salary until we grow more? I created this system that operationally it works seamlessly. All the systems are integrated together, you know, with time, I figured out how to make that happen. Of course, also with the help of AI. And I ended up in this operational role that at first it was confusing, but I feel like it's an important part of the process because how are you going to improve a system if you don't know the company from the inside? So I accepted the operational part and that was like a year and a half of only operations and perfecting it. And then it grew more strategically, you know, now into investor relations, fundraising, creating events. We are now creating for organizing our first animal general meeting for all our LPs and, you know, I'm trying to do a well factor there. So now you've got your hands and lots of other parts of the organization. I'm curious like from your perspective, how do you feel being a chief of staff at a VC fund is different from working as a chief of staff, say at one of the startups in your portfolio? What are most people picture that when you think they have a wrong? I don't think it's too different in these sense because this company was created from scratch. I'm guessing portfolio companies are also created from scratch. But in this role, you don't only support the leaders to make a deck and pitch this company and pitch to the other one, like depending on what industry they are, right? If they're in tech, but in fundraising, you do have to think about the thesis of why you're fundraising, you have to give it meaning. You have to sell the location you're selling into. Like if we're investing in Russia, we have to sell Brazil and Latin America. We have to convince this LPs, you know that if they invest in our fund, it's because we're investing in a country that has a lot of potential that doesn't have enough growth capital. So it's other terms at different strategy. And when it comes to like response abilities, you have to think how can you better support your executive, but it's all related to fundraising and investing. Yeah, so if the goals might be a little bit different, then it'll start up. But some of the fundamentals that make up the position are pretty similar. Most venture capital firms are not growing at the speed of light in terms of headcount and maybe even revenue, if that's even their goal, obviously returns a little bit different. The chief of staff is very much a dot connector between different parts of the organization, between different teams. And for a company of venture capital firm whose, you know, main goal is not necessarily growth by all means and growth usually comes with headcount. And nature of the role doesn't evolve in the same way. So I think there is like one difference there just in terms of how you work with, not just your principal, but the rest of the company, which is worth exploring. Yes, no, definitely. That's actually a good point because on a small investment firm, first of all, a huge difference is not only on the industry, but is the headcount. And I feel like that changes the role of a chief of staff, depending on, you know, the headcount, if you have five to ten people, if you have five, if you have seven, or if you have a hundred plus. But usually this is like you said, we don't need that many departments. It's smaller. People have a lot of agency, you know, partners and associates that are only focused on investments. You have a team that is only focused on investments and another team that is only focused on fundraising, which is the leadership team. So you have to support them. That's why it becomes operational because the little motor, it's a car, the entire machine, the motor, you have to set it up as a chief of staff so that it can run smoothly. So it can run better. And you're at the same time, the gaps that keep it going. The leaders are not going to think about operations strategically and the system and the partners are just going to be focused on meeting founders. So the responsibility is changed because of that. But I think they also change because you need more agency when you're supporting a venture capital firm, meaning a lot of the strategic initiatives are not born in either side of the fundraising or investing, are born in a chief of staff role. And you are located in a tower where you can oversee the little organization and you know what's missing and you know what's coming and you're the one proposing initiatives to change the system, to make up the fundraising strategy and process better, to make sure the team goes to this conference because it's worth meeting these people. So you start thinking about ecosystem building and strategic initiatives. There's an interesting dynamic app play there that I'm hearing, which is the chief of staff. In your case, at the growth fund, is almost operating like a mini CEO, right? Helping to set the kind of strategic direction and making sure that all of the players within the fund are focused on the right things, right? So the investors only want to be focused on new deal flow and getting their fund into the best business as possible. And that doesn't necessarily mean that they want to spend their time on the operations, on the people ops, on the other strategic priorities that might be beneficial to the fund if given more time and capacity. And so for you as the chief of staff, that's where you kind of have this bird's eye view to say, all right, directionally, this is where we all need to be headed. How do we make sure that happens? In addition to like, how do the day-to-day things just work on a regular basis? Absolutely. Another thing that you said, you know, the role, the responsibilities grow with the team growing too. In my case, for example, responsibilities and the growth of the organization has been insane. More things are falling on my plate by default and it's because I know how the company is working, right? So one example is we are creating an ESG department. We didn't have it before, but now that we've been running for three years, some of the LPs do require for us to have ESG officers of people prepare. So responsibilities do grow, but it's based on the growth of the funds now and people. Which I think probably leads to a lot of ambiguity, right? Yes. Let's talk about our favorite word, ambiguity. Most people probably treat ambiguity in any role, but the chief of staff role especially as a problem that they need to solve. We've talked previously. I know you see it differently. Tell me a little bit about how you approach ambiguity and why you think it actually leads to a lot of power in the position versus a challenge that needs to be fixed. So get ready because this is my favorite topic. And I might get excited. So a lot of people see ambiguity as a problem, because things are not clear. They're uncertain. There's multiple possible interpretations. There's so many paths, so many solutions. And a lot of people work with a job description, with metrics and they need to like, what be in a box, but they need instructions to know what they're doing. I understand completely that it, but a chief of staff will see the ambiguity as a chance to evolve and an opportunity to create value. So I feel like ambiguity is a space where value is definitely created. You have to understand that it is not a problem. Problems don't belong to a single department. And you have to actually put a white lens, see the entire company, see the different paths and come up with solutions and part of coming up with a solution is embracing ambiguity, questioning the status quo and saying how can I make this better. So with no ambiguity, I feel like the role wouldn't be what it is. Because a lot of companies, they're looking for a chief of staff because things are not working 100% well. A leader or an executive won't tell you, this is everything that's not working. I need you to help me with things. You have to have the initiative and you have to have agency. You have to embrace the ambiguity. You have to question the status quo and you have to analyze what the blind spots are. They will certain things give you an opportunity to create solutions and to actually give it meaning. Like I said, to add value and to engrave your DNA of problem solving and strategic thinking into the company. And that's how your role evolves. Where ambiguity doesn't matter if you solve one problem and if you figure out one path, it keeps popping up. And it's good to recognize it and actually use it on your favor. And in the favor of the company, of course. There's one thing to be said about, can a rigid role definitions that create a limit to the impact that you can have because maybe the job description was framed a certain way. And you're now in a position that feels less like a chief of staff role and more like a functional leader role, like looking over a particular part of the business. And that might be fine for a limited time. It's another thing to be said. Because there's various ways out of that. In terms of redefining what we're having conversations with your principal. Yeah. There's another thing to be said about the self-imposed boxes that we create for ourselves of like, well, I'm good at this or I've been doing this for so long. And therefore that is my responsibility. How do you practice the discipline of just constantly breaking out of those self-imposed boxes? There's two things that I like to think about, about ambiguity and what you're saying. If the chief of staff role were fully defined, it wouldn't be. as powerful, not impactful. Ambiguity is not a problem to solve, but it's a space for the chief of staff to come in and make it better. And for me, every quarter, I have a meeting with two years that I recently hired, and I start outlining the entire system, what's working, what's not working. For fundraising, I talk with my boss, for like anything operational, I talk with them. And even if things are running smooth, I always ask, like, how can I make this better? And I train them to have the same mindset, regardless of the ambinease, because when you're in a startup, you're basically your own agent. And I try for my entire team to have that personality that they come up with solutions. So I'm training this CA to actually question, how can they make anything better for the EA that is working with one of our executives, it's like, how can you make his life better? He's relocating. How can you make that relocation better and smoother, and like less stressful for the executive? So it's sitting down and analyzing what's working, what's not, and seeing the opportunities of improvement, and there always are opportunities. Like something might be working, and this has happened to me a lot throughout, like these three years in this company, but it could always be reshaped to be better. And with better, I mean, efficient, cost effective, better for the team performance, and also simpler. I have a good story for you. This is related to this, because when you crave value, and you want to change things, people think, I'm just adding more things to my plate, but you're not. Your responsibility is to make things better, and you have to be basically available for all the things that come in, and you have to be strategic to reshape them in favor of the company. When I was at Softbank, I had an executive, the one that hired me, Brazilian, Pablo Basoni, and I loved him. He was great. He taught me so much, and I would say that he prepared me for this role of chief of staff. He thought like a chief of staff, even though he wasn't, and he was my mentor. He did two things. One, I would text him a lot. I remember I would text him, "What's up? We communicated, what's up to plan everything?" And I think he didn't like that I wrote so much, so one time he gave me a book that's called, "How to Write With Our Bullshit." And I'm like, "I don't know if that's an insult, or he just wants me to make it better." And I read it, and I liked it a lot, because he helped me simplify systems, communications, emails, to make it straightforward. After I read that book, he gave me a task to print little stickers that say, "The word simplify," and he made me paste it on everything member, meaning 70 people of the Latin American fund for self-bank. And then he gave us a chat about simplifying, right? So when I sit down with my EAs, and I see the system, what we're doing, it's a lot of tasks all at the same time. It could be overwhelming for everyone. So it's like, "How can you make this better? Like this? You know, we come up with a solution." And then I think about simplifying the process, to actually make it effective, less time consuming, and gives you time to actually prioritize your tasks. So that's the route I take to be strategic, and not only like think on the box, you don't have the white lens that the chief of staff will require to see the gaps, to see the blind spots, to identify, you know, a team member there is not doing well, what's not working for him. So you're gonna talk with them, "Hey, you're not the manager for your chief of staff, what's going on? How can I make it better for you? What's working? What's not working?" And then you analyze from that. But a chief of staff always not only, like I said, "Operation, I'm not only to work the leader, you have to think about the system, and you also have to think about your team." It's a thing about the entire company. - Yeah, the phrase that came to mind while you were speaking is founder's mindset, which doesn't mean that you need to be a founder on paper. You know, my definition of that is really like, every problem is your problem. That doesn't also mean that every problem is your problem to solve. But it is within kind of your remit to make sure that those things are solved, meaning you're helping to direct and orchestrate, ensuring that the highest priority items are being paid attention to, and you need the widest lens to understand all of the problems, to know what the prioritization should be. A founder's mindset is, yeah, like you need to be in the weeds, as much as you need to be in like the high level strategy. But for me, it's all about solving problems, and you need to understand the breadth of the issues to really make sure that you're spending the time appropriately. - And I like that you said that it's also about orchestrating, right? Like, I think about, in my role, it's funny. I always compare it to the drummer. So it's like, I'm dictating the rhythm, and everybody's going at that pace. So as if a staff, I would say, like, it's also the drummer. You're dictating the rhythm, you're dictating the pace, and people actually go at that pace without you imposing. And you're doing a sort of way without being, you know, authoritarian or direct. You do it by having one or one of the people checking on how they're doing, seeing little gaps, seeing weaknesses, trying to strengthen them. One of the things that I did that I can compare it to this was, we had three partners, we have one managing partner. Our managing partner travels a lot to conferences. It's exhausting to travel so much, especially when you have the fundraiser, and you have to work. And I'm like, how can I make it better for this? So I spoke with my team and I asked them, how would you feel speaking in a panel at a conference on behalf of bicycle? And they were a little shy, they didn't know what to do. So I placed them in different panels. I went, I observed, I thought they were good. One had to project their ways a little bit more. So I just flew them to Miami for an outside, and I hired a public speaking coach that is also a stand-up comedian. And he gave them a week of intense public speaking lessons. And he made them feel uncomfortable. He recorded them. He made them see them on the screen. And now, they might not be at 100% because it was just one week, but they're more prepared and more confident when they step into a stage. And now the managing partner, whose my executive doesn't have to travel to all these conferences. So it's like little things like that. If I'm just an EA, I wouldn't think so strategically about it. My boss is going, he's fine. You know, I wouldn't think this is a lot of weight on his shoulders. I asked him, how are you doing? I want to spend more time with the kids. OK, let's make it happen. Let's send the partner who can go. Who should be better to go? So it's definitely a lot of orchestrating. Besides, you know, the operational or strategic part of the role. Yeah, it's also a great example of scaling. In this case, the capacity of the team, right? So that there's not only one stopgap to fill in that specific part of the operation. You now have multiple people that you can tap on. Talk to me a little bit about building capacity, generally, as a Chief of Staff. There are a few options kind of available. One of them is obviously hiring more team members. And, you know, typically with under a Chief of Staff remit, sometimes you see executive assistance. I think in some cases that those make sense. In other cases, I've seen biz ops teams potentially report into a Chief of Staff. If it's very like strategy and ops heavy work, then that becomes more part of the office of the CEO. In a lot of cases, Chief of Staff are not managing anyone directly. Talk to me a little bit about how you've scaled yourself as a Chief of Staff. If it's not human headcount, it could also be a Gentick headcount, which is another option. Not just, of course, starting with the worst simplify when I created this back office, which is HR, which includes benefit, some payroll and taxes. And other things that I didn't know require until I started doing it. IT, accounting, and then financials, they're different, financials and accounting. I didn't know that. We have legal compliance. Now ESG, IR, like all this, I created a system of platforms and AI and also consultants that I hire per hour when I need it. For example, the financials I hire are consultants, CFO that doesn't work inside of the organization. And I said, this takes most of my day. Like it takes four days of my week to be fully doing this. I have to have weekly calls with each consultant or spend time in these platforms and all these things. And I'm like, how can I get rid of all these HR stuff and responsibilities that I'm doing that I shouldn't be doing every day without hiring an agent? So I look into it. When I open this HR platform, I open our own entity, create our own account. And I had to start running payroll. But we have people in Miami, in California, and New York. And then I didn't know that I had to open a workers' conversation insurance for each state. And now I run everything in this platform with having to worry about its urances, with having to worry about producing W2s. Or how the benefits are handled. They handle everything for us. And this is something that I didn't know existed. And with this process, just changing into this, we're saving like $600 a month on just consultants fees. I already have more time to spend time in other things. How do you figure out what stays on your plate versus what gets delegated? Like at what point do you say, okay, it's enough of me doing this. I either need to rework the operational process so that it requires less of my time. Or I need additional human to come in and take this work over. Where is that breaking going? I am actually in that process and this is what happened. I hired this EA and I said, you know, you do anything related to the executive. Because I was helping him with like scheduling some calls, some minutes for meetings, and these things that also took my time. But I never needed the extra help. But I delegated anything administrative or, you know, that could be confused.
with an EA role, let's say, to her. Plus, you know, helping me with other operational things. And I felt like I was overwhelming her because it was a lot. It was a lot on my plate and falling on her plate too, because the ESG department then fell on my two and I made her ESG officers well. So it was a lot. So I flew one of R.E.A.'s from Brazil to Miami. And I sat with them and I wore. This is like the messiest way you can do this, but this is how I did it, and it worked. And I said, listen, guys. I need you to help me to let go of something. So I'm going to write everything I'm doing. So I wrote like the department by department, I started like going crazy, I'm staying mode on the board. And like every responsibility that I was doing, all the events that I was creating, all the partnerships I was working with, all the conferences that I was working with with my boss and the content for his presentations. Inside every department, there are so many steps. And what I do with IT, the onboarding, the off-boarding, the workstation setups, the office management, because I managed the office too. So I said, everything I circle on red, I can't delegate because it's strategy, confidential, like HR and payroll, but everything else is subforgrups. Who wants to help me? So we had a discussion and they started saying, I can help you with this, I can help you with that. We put it like an AI companion, meeting notes, even though we were in person, so it would help us get organized with the next steps. And now I meet with them twice a week with a project list when I put like who is in charge of what, with the deadlines, and I am learning myself how to delegate. It's really hard to delegate when you build something from scratch and you're so like overprotective of what you've done. And there's always like, I think I can do it better and you do it yourself. But like stepping back and saying, I am delegating, I'm not going to monitor. I already trained you for two months. This is your project take over. Now if there's an issue with that, then I have to have a conversation with them. But the question you just asked, this is something I'm going through and I'm learning how to delegate. It's not easy. I understand. It's important. It's important for the growth of the company and for you as a professional. Given what you've learned in your chief of staff role, thus far a bicycle capital, what is one thing that you tell someone new stepping into a chief of staff role at another VC? I will say, the goal of a chief of staff is not to do everything, but is to design an organization where the right things happen without constant intervention, first of all. That would be like one of the most important things I will say. Definitely learning how to delegate as the company grows. And when you see systems in a company and you feel like they're working correctly, you have to sit down and analyze it and think that every system should remove friction, not create it. And sometimes friction can be overlooked because you're just used to doing it. So never be comfortable with how it's running, always have that mentality of like Western in the status quo as well. And while we're talking about embracing ambiguity. Is there a question that you wish more to use a staff would ask them so much? Yeah, definitely. I will say that they should think if they are thinking inside that box or thinking outside it, if they really have a good feel and understanding of how the company runs, it also, I guess it depends on the size of the company. And then start looking for the company's running perfectly. You know, my boss is perfectly. So that start having more initiative and agency when it comes to communicating with your executive don't wait to receive instructions, but actually ask him, look for one or one's, sit down with them, have a feel about what they're doing or what they're uncomfortable with if they're trained and where, you know, like why are you working right now? I feel like a lot of chief staff don't ask their executives why are you working right now. And then they tell you, no, I'm doing this and I'm doing that, I'm building the thesis for the second fund. I have to figure out how fundraising works. I don't know how to track all the LPs that I'm meeting. Then just like, let me help you with that. And then you become proactive. It's not a production of a day to day, it's a production of the entire organization and the system. So you have to always ask questions. You cannot just sit there and wait for things to happen. You have to be involved. And part of that is having agency and initiative and speaking up. And with speaking up, I mean ask questions. The question that you just proposed, what are you working on today? Is a really simple one, but a really effective one? Probably something that is easily taken for granted. I'm just assuming rather than really acknowledging where that time is going. Yeah, it's a simple question. And again, the concept of simplicity doesn't revolve just around how the system works. It revolves how you think because there are a lot of simple questions you can ask that will give you a hint of what could be better. And I'm using the example of that question, because history really stress with the fundraising process. And I want to sit with him and I want to help him propose, a platform where we can track all peace. How can we integrate it with our outlook so that it can be updated, dividing our own peace by location, maybe going to a conference with our location and having an entire day of peace with those health peace are in that location. So helping him be more efficient will help the entire organization. Stephanie, this is a great conversation. I really appreciate the time today. Thank you for joining us. Thank you Scott, you're the best. All right, that's a wrap on my conversation with Stephanie. A few things I'm still thinking about. The drumming metaphor really stuck out to me. The idea that the goal of a chief of staff isn't to do everything, but to design an organization where the right things happen without constant intervention. And honestly, just a reminder that asking your principal, what are you working on right now? What is your highest priority? Is somehow both the simplest and most underrated question in the role? If you enjoyed this one, please subscribe, leave a review, share it with someone in the chief of staff world. It genuinely helps us. We'll see you next time. (upbeat music) (upbeat music)
Podcast Summary
Key Points:
Stephanie Agreco is Chief of Staff at Bicycle Capital, a growth-stage venture fund investing in Latin America, a rare role within VC firms.
Her path to the role is unique, starting in Venezuela with a background in journalism, modeling, retail, fitness instruction, and later as an EA at SoftBank.
At SoftBank, she helped build a Latin American fund team and transitioned from an EA to a strategic Chief of Staff role, eventually leaving to co-found Bicycle Capital.
In a VC fund, the Chief of Staff role is operationally focused due to small headcount, involving setting up systems, supporting leadership, and driving strategic initiatives like fundraising and ESG.
Ambiguity is seen as an opportunity, not a problem, allowing the Chief of Staff to create value by identifying blind spots, proposing solutions, and shaping the company’s direction.
Summary:
Stephanie Agreco’s journey to Chief of Staff at Bicycle Capital is unconventional, beginning in Venezuela where she studied journalism to advocate for her country during a political crisis. After the media was shut down and her family’s oil business was expropriated, she moved to Miami in 2009, juggling jobs as a waitress, fitness instructor, model, and retail worker to build a new life. She later earned a degree in public relations and landed at SoftBank as an executive assistant for the Latin American Fund, where she helped managing partners build a team of 70 and oversaw strategic responsibilities beyond traditional EA duties.
Despite the role’s ambiguity, she embraced it, leaving SoftBank to co-found Bicycle Capital from scratch, defining her own Chief of Staff position without a job description. At the VC fund, with a small team of six, she focused on operations—setting up systems, platforms, and partner networks—before evolving into more strategic work like investor relations, fundraising, and creating an ESG department. Unlike Chief of Staff roles at startups, her work emphasizes supporting investment and fundraising teams, connecting organizational gaps, and proposing initiatives.
She views ambiguity as a powerful tool for creating value, allowing her to question the status quo, identify blind spots, and embed her problem-solving DNA into the company’s growth.
FAQs
At a VC fund, the Chief of Staff focuses on operational strategy, ecosystem building, and supporting a small team of investors and fundraisers, rather than managing rapid headcount growth. The role involves setting up systems and proposing strategic initiatives from a bird's-eye view.
Her upbringing in Venezuela developed resilience and problem-solving skills. She later gained experience as an EA at SoftBank, helping build a team of 70, which taught her strategic thinking and how to amplify executive capacity.
She sees ambiguity as an opportunity to create value, not a problem. It allows Chiefs of Staff to question the status quo, identify blind spots, and develop solutions that shape the company's direction.
She created the role from scratch by assessing the company's needs, focusing first on operations and systems integration, then expanding into investor relations, fundraising, and strategic initiatives like organizing LP meetings.
She left a secure role at SoftBank to build the fund from scratch, with no payroll or entity in place for a year. She took a risk based on belief in the team and had to define her own responsibilities.
They set up integrated systems and use partners or consultants instead of hiring full departments early on, allowing the small team to focus on investments and fundraising while the Chief of Staff ensures smooth operations.
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