Youssef Ahres is the Co-Founder & CEO of Flagship, a company striving to build a fair and equitable creator commerce ecosystem. They are backed by Sequoia Capital and Index Ventures. Before that, Youssef was a Director of Data Science at Instagram.
In this conversation around career growth, we cover various topics, such as:
- The role of a manager
- What to look for when hiring
- How to retain top performers
- Why some people get promoted over others
- Big tech vs. startups vs. starting a company
- How to pick a good startup to work for
- What you must get right to have a meaningful career
- And more!
Kieran: Thanks, Youssef, for joining me today. To kick us off, do you want to introduce yourself?
Youssef: Hey, I’m Youssef. I’m the Co-Founder & CEO of Flagship. In a nutshell, Flagship is an e-commerce platform. We allow creators and tastemakers to set up online businesses where they can feature their favorite products. Before starting Flagship, I spent six years at Instagram, where I was most recently a Director of Data Science for all the Ads and Commerce teams.
Kieran: When you were recruiting for your first job, Sanchan, the Head of Product of the Instagram for Business team, made a compelling pitch for Instagram and why it would become the place where people would buy online from businesses. What do you remember from that conversation? What made his pitch so compelling?
Youssef: Oh man, you’re throwing me way back. I think there are a few elements of that pitch, but before we get into it, I think it’s important to baseline the context. So, that was really my first job, and like many people looking for their first job, I was looking to sort of make my mark and learn how to make an impact on the world. I had just joined Facebook, and I was talking to a few teams. One of them was the Facebook Marketplace team, which was just starting at the time. One of them was the Dynamic Product Ads (DPA) team. It was an exciting business and, at some point, became 30% of Facebook’s revenue. One of them was the Instagram Business team. When I was looking at all of these teams, the one thing that I was trying to understand is what are the drivers of the decision. What should I care about? It came down to three things. The first one was is there a future here? Is this going to be big? Is this going to be impactful? That is the objective analysis of any team, product, and company. You should be looking at it and thinking, hey, will this go somewhere? The second element is the people. You mentioned Sanchan. Sanchan was a great partner. As soon as I met him, I was like, hey, this is someone I will learn a lot from. The third one was mission alignment. Do I genuinely care about this? That’s where the Instagram Business team truly stood out for me. My father owns a small business. I lived all my childhood at the rhythm of his business. When the business did well, we were all delighted. When the business didn’t, we were all sad. I made it a little bit of my life’s mission to help people with that journey, and the Instagram Business team felt like the right place for me to do that at the time. That is what sort of leads me to Flagship today. It’s sort of the same mission all over. Now, going back to the pitch. I think a good pitch from a hiring manager or someone hiring for a team is very upfront about the good and bad things. What are the sacrifices you will make, and why does this mission matter? What’s more important than selling the person and why this will be huge is whether this person will be excited working in it. For better or worse, Sanchan was very clear that it would be a lot of work. But guess what? I was excited because that’s what I was looking for.
Kieran: Was Sanchan your manager?
Youssef: No, Sanchan was the Head of Product of that team, and he left a few years later. My manager was Jenni Romanek. She is now the VP of Data Science and Data Engineering at Instagram. I worked with her for all my time while I was there.
Kieran: How would you describe her as a manager?
Youssef: Jenni is the best. Obviously, I’m biased because I learned everything regarding management from her. She’s an incredible manager. Here is how I think about what’s a good manager, or at least what I try to hold myself accountable to. Management is a practice that aims to enable people to achieve their greatest potential. Now, if you’re a leader of a team, management is a component of your job, but not the entire job. That’s a confusion that some people have between management and leaders. In reality, if your goal is to be an excellent manager of a team, then you have to help them grow. You have to help them crush it. That comes down to helping them shoot very high. They have to have goals far above what they think they can achieve. Second, you need to empower them to achieve those goals. Sometimes, that’s coaching. Sometimes, that’s going on the ground to assist them with solving a problem. Sometimes, it’s removing roadblocks and getting people out of the way so they can execute. Sometimes, it’s allowing them to fail. It’s okay for them to fail. You have to have their back if they’re doing their best work. The third thing is holding people accountable. It’s easy to shoot very high and try, and if it doesn’t work, then move on. I think a good manager knows how to hold people accountable. Holding people accountable doesn’t need to be adversarial. It’s not like, hey, you have to accomplish this or else. I think that kind of exchange is very unhealthy. If the report and the manager are aligned on the goal, it’s healthy to check in every week and see how they are progressing. Managers are well equipped to keep reports accountable because they sit outside. Sometimes, you need a third party to observe the trend to give you feedback and hold you accountable.
Kieran: You’ve talked about the power of checkpoints in your career and understanding where you’re progressing and where you’re not. What were your checkpoints for the audience wanting to start this practice for their careers, and how did you structure them?
Youssef: I was catching up with one of my former reports last week, and she asked me, “The team used to run a certain way, and I’m trying to make sure that my team runs similarly. What were all these best practices and processes that you had in place?” I think people tend to overemphasize processes. They’ll be like let’s meet weekly or bi-weekly, and here’s a template. I think all of that has its place and can be useful, but it can lock you into a process that doesn’t have a place to live. Many people don’t like working in big companies because it’s sometimes over-processed. But, in practice, the way I think about checkpoints for myself, regardless of how I achieve it, has to abide by two clear principles. First, I need to set up measurable goals. I need to be able to measure whether I’m succeeding or not. Maybe I’m too much of a data scientist by training, but if I can’t measure it, then I don’t know if I succeeded or not. That’s really a practice of defining clear goals. The second one is intellectual honesty. I have to be able to look back and say, hey, did I achieve this goal, or maybe I haven’t? If I haven’t, perhaps the goal was too aggressive, or I need to improve. In my personal life, I check in with myself twice a year for my career. I see what I’m doing. Am I happy? Am I not happy? Am I growing? Am I not growing? That’s one of the reasons why I ended up leaving a job that I loved at Instagram. I looked back and realized that I wasn’t growing at the same rate I wanted to, and I felt I still had a lot to learn. That was the trigger for me. Similarly, now, I have a much shorter feedback loop. I’m trying to get better at working out more often because I lost a lot of my good habits when I started a company. It’s really sad to see. But, now I’m failing, and so every couple of weeks, I check in with myself. How many times did I work out in the last week? So, it depends on what the goal is. But first, you define the goal. Then, you determine the structure to hold yourself accountable to the goal.
Kieran: You have hired lots of people throughout your career. What questions do you like to ask during interviews? What are you looking for?
Youssef: Hiring people from different functions leads to very different questions. Hiring an engineer from a skillset perspective differs greatly from hiring a marketing person. But there are common threads. I’ve interviewed every single person at Flagship, and I will continue to do that. The common thread I look for is the following. To define whether the person will be successful, I look for three things. The first thing is, can this person work very hard? I don’t think anybody can achieve great things if they don’t work very hard. I think working hard is a prerequisite. That’s a lesson you learn when you realize how much commitment and effort goes into something if you want to achieve great potential, regardless of your starting point. I saw this first-hand when I watched how hard my little brother worked to be a national champion in tennis. That doesn’t mean everyone has to work 12-hour days, but if the team needs you to ramp up or there is an occasion one needs to rise to, will this person be able to rise to that occasion? Do they have that capacity? Number two, is this person passionate? They don’t need to be passionate about the same things. Some people are passionate about the mission. Others might be passionate about the system, the problem, or the customer. It doesn’t matter to me. What I try to understand is there a passion there. Is this something that will get them excited to be thinking about when they are hiking on the weekend? Or will this be a 9-5 job unless they have some near-term goal like a promotion and will stop working hard the other times? The third thing is, are they team players? This is a lesson that I learned the hard way in management. Sometimes, you have strong individual contributors who are incredible at their jobs but can have a negative impact on everyone around them, and they can pull the entire team down. I think most managers shy away from getting rid of these people. I learned that you shouldn’t. The environment can become very toxic very fast. I’d rather spend a little bit longer looking for the right person rather than having a strong contributor who doesn’t fit into the culture. I think culture always trumps individual contributors.
Kieran: When evaluating people internally for promotion, what do you look for? Why do some people get promoted over others?
Youssef: I’m going to sound like such a Facebooker right now. The only thing I look for is impact. Can this person drive a lot of impact? Are they driving a lot of impact actively? Sometimes people get upset because they’re like that person has a lot of visibility or whatnot. I don’t think any of that matters. It’s the role of the management to make sure that the people getting promoted in any organization are the ones who are driving the most impact, and I think it should be pretty visible. You’re trying to create an environment where there are examples that everyone wants to follow, and that example should be based on impact.
Kieran: You’ve shared that teams should focus far more on retention than hiring new people because of the compounding effects of teams working together over long periods. What tactical things can you do as a leader to ensure you retain your best employees?
Youssef: I think it’s one of the most debated pieces in management circles. For example, whenever a senior position opens up, do you hire someone new who comes in with loads of experience and can bring in knowledge that you don’t have on the team, or do you promote internally and take a bet on someone? Different people fall on different parts of that spectrum. I don’t know who is right and who is wrong. I can tell you my management style is far more on the latter. I tend to bet on internal talent. Part of the reason is what you just described. If you do that, retention is not guaranteed, but far stronger because people see a path forward. I fundamentally believe that most people are looking to grow, especially ambitious people. What they are looking for is I want to build something great, and I want to grow on the way. If you could provide those two things well and effectively on an ongoing basis, then retention tends to be high, at least among top performers. You need to be the one providing the path. When I was at Instagram, our team was reasonably large. By the time I left, it was around 40 people. What I held every manager on the team accountable for is every individual contributor should have a path forward. I don’t care if it’s written in a template. I don’t care if there’s a plan to get them from one level to the next because that’s the easy part. The hard part is deeply understanding what that person is shooting for and whether they have a path to actually get what they care about. Let’s not lie about it. They are not going to stay there forever. But, your goal is to provide them with the best environment to stay and be productive. If you did your job well hiring, then what you’re aiming for is growing people at an exponential rate. To do that, you need to have a clear idea of what that path looks like for their growth.
Kieran: After six years at Instagram, where you loved to work, you left and started your own company, Flagship. What framework or advice would you share for people evaluating big tech vs. joining a startup vs. starting a company?
Youssef: I think it’s tough to generalize. I can speak to what are decision factors that come into play. I think people are fascinated by risk. I believe this leads to a tendency for people to think being a founder is the best. I don’t think that’s exactly accurate. Being a founder can be really hard. But, I think it’s a game that biases towards people who have the opportunity to afford it. I was excited about starting a company in grad school, but honestly, I couldn’t afford it. That’s the reality. I am an immigrant in this country, and I wanted to be with my now wife, Inez. For her to come, I need to guarantee some path for immigration papers and all of that, and it’s surprisingly hard. I think you’re from here, but if you’re not, you’d understand all the H1B and immigration stuff is very difficult. Also, Tunisia, my home country, is going through an economic crisis. I needed to be there for my parents financially. So, for me, it came down to what are the constraints that I operate under. I think most people have constraints they are operating under. Based on those constraints, what are you optimizing for, and then you can figure out your path. For me, that came out after Instagram. To your point, I loved my time at Instagram. I would love to spend more time there. If time was infinite and I didn’t have a finite amount of time on this planet, I would have probably stayed longer. I was having a great time. The people were amazing. I loved Jenni, Ashley, and everyone there. But, at the same time, to my point earlier, you know everyone is looking for growth. Honestly, after six years, by all measures at Meta, I still had growth left. I had a few promotions that I could probably get in the next few years. Compensation would have continued to go up. It would’ve been great. I’m sure I would’ve enjoyed it. But at the same time, I looked at myself and was like, well, am I growing as fast? Am I learning? Am I being stretched? The answer was no. The reality is I knew what I was doing. I was part of the team that helped to monetize Instagram Stories, and it was time for Instagram Reels. I don’t know if you saw the earnings call the other day. Reels monetizes very well. It’s the same team. So, you know, you go through these periods in life where you accelerate, where it stretches you out, then it slows down, then it stretches out, then it slows down. When you’re spending too long in one place, and you’re not being stretched out, then you should ask yourself the question, am I in the right place right now? If I look back 50 years at this period, will I regret not doing something else? I think Jeff Bezos calls this the Regret Minimization Framework. I think it’s true. I looked at myself. Will I regret it? I was like, yeah, let’s do something. So that’s when I started looking into my mission in life, what I really care about, and that kicked off the journey to what is now Flagship.
Kieran: For job seekers looking at startups, how would you identify a good startup to work for?
Youssef: One thing to understand about the startup ecosystem is it’s extremely opaque. It’s not like the public markets. For example, Flagship has been around for a year and a half. I bet you have no idea what our metrics look like. There’s no way for you to know because they are not public. We don’t share them. We don’t have an obligation to share, and we don’t want to share until we feel ready. So, if someone is interested in going into startups, I would tell them to stay off their computer. Don’t go and Google and Glassdoor Search. Just go talk to people. That’s the only way to know. It takes longer because it’s not as efficient. There is no S1 to look at, and no earning calls to listen to. It’s a little bit more complicated to find something you’re really excited about. The best information, the rough diamonds, exist in the community. If someone is interested in healthcare, what are the top VCs in healthcare? Start there. VCs love to talk to everyone because it’s their job to know everyone. I would start by building a great network and by joining the community. Find these proxies. VCs are typically a good proxy. If someone is backed by a good VC, typically, there is a story there, and they are happy to make intros. I would start looking into the communities and trying to dive deep. What are the real problems? For example, if you tell me you’re interested in ads, I would tell you, well, look at privacy, what’s going on in privacy? Privacy has been one of the most significant tectonic shifts in ads in the last 5-6 years. What’s going on there? Who is going to win that race? Who is going to win the race of advertising when there are no more cookies in the world? People develop expertise in these areas, and the more you talk to people, the more you get a view of what will really make a significant change in the next few years.
Kieran: For people wanting to start a company down the road, what are the best things they can be doing today? What skills should they work on, what network should they develop, what environment should they put themselves in, etc.?
Youssef: That’s a good question and something I had to reflect on. During my time at Instagram, I was on the builder side. We were building a lot of small times, and at some point, I moved to management and org leadership. Some parts are relevant, but most of my work looks more like my first years at Instagram than my latter years. The main thing for me is if you’re joining a small company or starting one, you want to be a builder. You want to be someone who thinks from first principles. If you’re an engineer, for example, what you don’t want to do is go into a very established team working on iterating over algorithms or over specific UX’s based on robust design systems that are in place. What you want to do is build the system. So, if you’re going to a big company, looking for teams earlier in their lifecycles is far more beneficial than going to very established teams. If you are open to startups, then the earlier, the better. If your goal is to start a company, then you want to go to the earliest possible stage because you want to be part of setting the foundation upon which the company will be built. After all, that will teach you how to build the foundation down the line. It turns out that optimizing the Instagram Ads system and building Flagship is very different.
Kieran: You’ve been building Flagship for just under two years. Reflecting on the journey so far, what have been your biggest learnings?
Youssef: The thing that shocked me the most, and I had a good adjustment period, is when you work at a big company, especially a cool one like Instagram, you come with the benefit of the doubt. If you reach out to anyone, honestly, they reply, whether that’s a candidate, customer, or friend. If you reach out to anyone and tell them you’re a Director at Instagram and want to help them, everyone will reply because you come in with this credibility that is Instagram. When you leave Instagram, it doesn’t matter if you’re Ex-Instagram. You’re a nobody. You’re on the same line as everyone else. What I didn’t realize is how much everyone gets pitches all the time. So, my first few months were a lot of hustle. What I was trying to do was explain to people what we were trying to do and close design partners. A lot of the people I work with are using the tools that I helped build. I’m very familiar with their use cases and how they use Instagram. Getting past that first line was much harder than I thought. I think what it comes down to is you have to earn the right for people to care about you. I think that’s the biggest learning for me. The reality is when you join a company like Instagram, Instagram has earned that right. Kevin Systrom earned that right a long time ago. When I joined Instagram, I was surfing on the efforts of Kevin Systrom when I built and reached out to people. But building that from scratch is really difficult. That’s why I mentioned if someone is thinking of starting a company, joining a company at a very early stage will show you how people can do it. I think Flagship is starting to actually have a name, even though we’re still pretty hidden and not trying. People sometimes tell us they’ve seen Flagship everywhere. Not many people, but a few people say that. So, it’s starting, but it did take us six months of hustle since we launched Flagship Stores and about a year and a half of work before that.
Kieran: "Earn the right for people to care about you." How did you go about doing that? How would you frame that for someone trying to do that for their own company?
Youssef: For me, it came first and foremost from happy customers. The number one way we get brands and creators is through the network by doing good work. There are different ways you can do that. I’m wired in a very Facebook way where I always look for K-factors. I always look for ways to make my network grow by itself, which is how Instagram and Facebook grew. In reality, I think people do it differently. For example, I know some founders who were very successful at building an image for themselves. If you stand out as a thought leader in that ecosystem, then people look up to you, and that will translate to your company. In fact, that’s the feedback that I got as a founder. I was told I should be more visible. I should be talking more about ads, influencer marketing, and how it’s evolving. But honestly, it comes down to prioritization too. Do I have time to do that? Straight after this call, I will go back to building and coding. It’s just a matter of where is the best place to allocate my time. You have to earn it somehow. How you earn it is a little dependent on who your customers are. Are you trying to sell to SMBs or enterprises? This is actually a big question. Because if you’re selling to enterprises, then you can use tools like Salesforce. If you’re selling to SMBs, then you can’t. So, you have to be a little bit more creative about how you earn that right.
Kieran: How do you think about risk tolerance as it relates to one’s career? When should you take risks in your career?
Youssef: Yeah, I think there is a real fascination. The common wisdom is to take risks while you’re younger. Everyone is like, oh yeah, you’re young, you can afford it. Because you can afford it, you should probably do it now because maybe later you won’t be able to. In practice, I think it depends on the person’s risk tolerance levels. Being more risk-tolerant is not necessarily better. I think there is this mindset that being a founder is the best. It’s not true. Honestly, I’ve done a bit of both, and the jury is still out about what’s better. Identifying one’s constraints is where I would start. You don’t want to blame yourself. You don’t want to be in a position where you’re being dictated by what society does. Ultimately, humans tend to mimic each other. We like to say this is how we think about the world and whatnot, but most of the time, we’re just thinking about what the 5 people we spend the most time with are thinking. Whether we’re considering starting a company or discussing what’s happening in the economy, we’re driven by that. So, I would start by identifying and understanding one’s honest constraints. Then it’s a matter of what will get you excited to wake up in the morning. If you do something that keeps you excited every day, you’re stretching, you’re growing. Whether that’s starting a company or working somewhere, it doesn’t really matter. That’s how I would think about it. I have to call it out because I find that at least in the founder space, or the founders that I hang out with, I think there is this perception that you must take a lot of risk all the time. In reality, not everyone can afford it, and I think we should be open to that as a society rather than trying to drive everyone down the same funnel.
Kieran: If you want a meaningful career, what is the one thing you think you must get right?
Youssef: I had to reflect on this one a lot recently because my wife was switching roles, and she had a lot of offers and was thinking about it. We were trying to figure out a framework of how to best think about it. If you want a meaningful career, what are the few things that are most important to get right? I think where we converged was you want to be in a position where what you’re working on is growing and you’re being bet on. An example is you want to be working on a startup that has a lot of potential where people are making bets. As a founder, you want investors to bet on you. You want people to bet on you. Ultimately, it’s about people taking risks with you. Every person who joins Flagship is taking a risk on me and my co-founders. It’s not a very established business where you can read the numbers. There’s a lot of trust involved. Similarly, if you’re going to join a company, is that company growing? Is that space growing? Is that product growing? Is there potential, somewhere it can go, and will people bet on you? You’ll be surprised at how much those two things in combination really compound. Let’s take it the other way around. Imagine you work on something growing, but no one is betting on you. You’re stuck because maybe they keep hiring above you. What ends up happening is you’re in a great company that’s growing, but you’re not growing as an individual within it. The other way around also doesn’t really work. If you’re in an environment that is not growing by itself, but people are betting on you, then everything is zero-sum. When the environment is not growing, if you’re taking a position, then someone else is not taking it. That creates pretty adversarial environments. I was lucky when I started my career to be in a place that was growing a lot. The Instagram Business side grew a lot during my time, and frankly, I had incredible mentors in management. You mentioned Sanchan earlier. There’s Jenni, Vishal, and Ashley. There are a lot of people who took bets on me. I think the combination of those two things can allow you to grow really, really fast.