 I'm Natalie Gibralter, and I joined Squarespace over 10 years ago, drawn in by the company's mission to make it easy and accessible for anyone to build a beautiful and professional online presence. And that anyone includes me. Years before I joined Squarespace, oops, sorry, years before I joined Squarespace, I built this website for the nonprofit that I ran on the Squarespace platform. Now I know that it's not much to look at now, but trust me, in 2010 this was pretty great. Instead of paying someone thousands of dollars to build this website, for a few dollars a month I was able to build a website that I believe added credibility to the work that we were doing and contributed to our early success. I was so inspired by how Squarespace leveled the playing field for ideas that when the time came to look for a new job, I knew that I wanted to be a part of Squarespace's mission. And there are so many stories like this that I've heard from our customers over the years. In fact, just 20 minutes ago I was talking with the founder of Product School, Carlos, and he was telling me that the first website that he built for Product School himself was on the Squarespace platform as well. Squarespace was very much a startup at the time, with about 70 employees and tens of thousands of customers. Fast forward a decade later, we are over a thousand employees, a public company generating millions of dollars and having millions of customers. So much has happened over these 10 years, and I got to be a part of many various stages of growth. The pattern that I saw repeated over and over again through those various stages is that what gets you to point A often won't get you to point B. There are operational processes, organizational structures, strategies, roles, people, approaches that work at a certain stage of a company that you might later outgrow. And the very same things that might drive your success early on can be exactly the same things that hold you back later on. So a key part of the journey to scale is being open, nimble, and willing to identify when you've outgrown something and able to shift to something new that will help you get to that next stage. It tends to be hard at times to let go of the things that drive our early success, and we can often hold on to them for too long. But being able to adapt and let go of the things that contribute to your early success are key to both long-term organizational success as well as personal professional success when you're in a growing company. As I was telling my friend and former colleague Andrew Bartholomew about this talk and the lessons that I internalized throughout those years, he told me that my talk made him think about how animals molt or remove the shells or skins that they've outgrown to make room for new growth. And I found this to be a perfect metaphor. As product managers, the essence of our role is being able to adapt to change, adapting to new market dynamics, to new consumer behaviors, new technologies, and, if we're successful, adapting with our organizations as they grow. Adapting to change is in the very fabric of our work as product leaders. It is so very natural to outgrow the shells that serve us at a certain stage and yet in the same way that a crab is most vulnerable in those moments of molting from one shell to the next, we too can find these moments very scary, especially when we're experiencing them for the first time. There's a reason why these moments are often called growing pains. But the key lesson that I've learned throughout these years is that change is inevitable. And if you approach it with interest and with curiosity, rather than denial and fear, opportunities can abound. So today I'm going to tell you about some of the pivotal moments of molting that I experienced at Squarespace over the past decade and four of the lessons that I learned through those moments that I hope might be helpful to you as well. Lesson one is narrow scope and go deep to grow. So let's go back to the beginning. I joined Squarespace in April of 2012 as the first business development hire. That function didn't exist at the time, and so my job description was pretty fluid. Squarespace had been working on a major replatforming for a couple of years that would allow us to serve a broader set of websites. And I was asked to think about two specific opportunities. The first was should we go after restaurants as a vertical and the second one should we pursue students as a market. I threw myself into these questions, developing a strategic perspective on each and also partnering closely with the engineering team to explore product solutions around them. One day over lunch, one of the engineers that I worked with, Thomas Chow, here he is, dear friend, told me how he was playing around with the new Stripe API that had just come out to build an integrated shopping cart feature. I found this idea fascinating, not only because this new technology was unlocking completely new possibilities for how we could serve our customers, but it was also different than anything else we had built at Squarespace. At the time, we explicitly built products for ourselves and scaled them to the masses. Our team of engineers and designers understood the problem spaces intimately well because they lived them. They were photographers, bloggers, artists, and had built Squarespace to solve their own use cases. However, e-commerce was different. No one on the team, not even Thomas, not myself, actually lived the experience of running an e-commerce business. No one was fulfilling orders, shipping boxes, or managing inventory. So I offered to speak to some prospective customers to better understand their needs, and that is how Thomas and I started working together on building the commerce product. Our new platform, Squarespace 6, launched that July, and by the start of 2013, we launched our commerce functionality. Here's the photo that Thomas took when we hit our first 100 stores. While working on commerce, I also continued the rest of my business development work. In addition to the product work, I was leading multiple large partnerships, having a lot of fun, and contributing to the business growth, which was moving at a very rapid pace. There was so much opportunity that my boss at the time, the COO, Jesse Hertzberg, knew that we needed to grow the business development function as well. I vividly remember the day that Jesse and I were in our weekly one-on-one meeting, and he told me that I needed to choose a more narrow category focus. In that first moment of hearing this, it was felt very hard and actually quite scary to make that choice. I was proud of all of the work that I had done, really enjoyed the breadth of responsibility, and I didn't want to give any of it up. Plus, I was afraid of making the wrong choice. But not choosing wasn't an option, and ultimately, I ended up shedding the shell of my first role and becoming the category manager for commerce. In retrospect, that ended up being the single best career decision I've made to date, but it was far from obvious at the time. Commerce ended up being a critical part of company growth, and today is frankly the core of our strategy and our future. And our company trajectory could have looked quite different had we not chosen to focus here so deeply at that time. But at that moment, e-commerce for SMBs was still fairly nascent, and it wasn't obvious that this bet would pay off as big as it did. Had I not reduced and focused the scope of my work at the time, I would not be the VP of product for commerce today. And as scary as that moment was, this ultimately ended up being an incredibly important lesson. To see the narrowing of focus not as losing something, but creating space to take on something else, something new that might be a new stretch. All too often, people feel like the only way to move up in your career is to take on more stuff, to broaden your territory. But often, moving up has more to do with going deep and demonstrating success and effectiveness rather than just taking on more. Both developing a mindset about your own scope as well as your team's scope if you're a manager, just as Jesse did, that puts strategic growth for your company first will often result not just in better business impact, but I believe also career impact for you and for your team. I saw this lesson repeated so many times over at Squarespace over the past 10 years, and it is not unique to us. If you align yourself with value creation and particularly strategic value creation, the rest will follow. Our second lesson is to be consistent with principles and fluid with rules. So from its very first days, Squarespace was a company that inspired creativity, valued the power of the individual and held the belief that great ideas can come from anywhere and anyone. These foundational principles were core to the products that we built and the work environment in which we built them. As I shifted my focus solely to commerce, these principles were at the forefront of my mind. I convinced the CEO, our founder, Anthony Casilana, that we should begin hiring engineers onto a dedicated commerce team to help them develop expertise in that customer use case, whereas before we just had one engineering team that worked on everything. And before long, five engineers were on the team. Here's where we used to sit at the time, watching our screens together as we hit some meaningful milestone. And having the team dedicated to these customers helped them develop a really deep understanding of their needs. The team was full of passion for these merchants and great and varied ideas for how we could better serve them. As the team was growing, so was our customer base and the variety of their needs. This was both tremendously exciting and also meant that we now needed a more defined and ordered way to prioritize which problems we would solve. My role evolved at this point to provide the necessary strategic direction, to identify the most valuable problems for us to solve, and then engage this team to unearth the best solutions together. And as a result, the team actually gained agency and became widely regarded as our most motivated team of engineers. It was at this juncture that my role evolved into more pure product management. But it was really scary for the organization to call my work product management. And let me explain why. Up until that point, there was no product manager role at Squarespace. In fact, the title product manager carried somewhat of a stigma at Squarespace. We had made it a point to entice prospective engineers to join our company with assurance that they would have full agency around what work they would do without a product manager telling them what to do. And the reality was that for the first number of years of the company, when we were smaller in scale, there truly wasn't a need for product managers. Our Anthony, our founder, was the head of product solving the needs that he had identified for a better way to build websites. And our development team, as we talked about, was full of photographers and bloggers that understood the problems they were solving innately well. So not having product managers worked really, really well until we got to a scale where it no longer did. Not having PMs at our smaller scale was designed to maintain the agency of the individuals on the team and was core to our building the initial stages of success of Squarespace and to the entrepreneurial spirit and culture that so defined that early success. And that's why it was scary to let go of that no PMs rule that had worked so well for so long. But it was undeniably clear that at the customer base and the employee scale that we had reached and at the rate of growth that we were continuing to experience, the role of product management in providing strategic direction and prioritization was now essential to preserve that very principles that had defined the company since its inception. At this point, developing a more nuanced set of responsibilities among the team members emerged as an essential roadmap to our growing success. So this was another molting moment for us. We shed the rule of no PMs and replaced it with a more nuanced view of how we could drive motivation, impact and efficiency by adding PMs. In mid 2014, I officially became the first named product manager at Squarespace. The commerce team proved to be a model that the organization wanted to replicate elsewhere. And by the end of 2014, other teams began hiring PMs as well. At this point, we had hundreds of employees, hundreds of thousands of customers, and the need for product managers was very clear. The core lesson here is that as you scale, the rules may need to change in order to adhere to the underlying principles. It's important to never lose sight of the principles themselves as they are the core part of the culture, so that you can be fluid with the rules when they no longer serve the principles. Our third lesson is codify rules and processes, excuse me, or in other words, write it down. By the end of 2015, we had surpassed 500 employees and over a hundred million dollars in annual bookings. We had multiple, thank you, we had multiple product managers across various teams who were hired by different functional managers with varying expectations of that role. And while early on it worked really well for people to wear many different hats with fairly fluid responsibilities and a loose structure, we now found ourselves at a developmental moment where consistency was starting to become essential. There was great inconsistency in how product management, design, and engineering worked together across teams. And almost more importantly, a lot of inconsistency around how those different product teams worked with other departments such as customer operations, finance, legal, and marketing. This began to create a lot of inefficiency as every team had a different way of developing and launching new products. Customer operations couldn't count on a consistent way to train and prepare their teams for a launch. Marketing couldn't have consistent expectations on how to partner with product teams to go to market. We had gotten to a point where there were enough interdependencies between these functions that having each product manager and their teams have their own ways of operating made it very difficult to be rolling together as an organization. It was hard to hold each other accountable and it created a lot of unnecessary frustration. Again, this became another moment of malting. We decided to centralize the product management function and my scope broadened beyond commerce as all of the PMs moved to report to me. We developed a set of guidelines on how we develop and launch products across the company. We defined consistent roles and responsibilities for all product managers and created our first product management career ladder and hiring process and we got it all down on paper. And while it wasn't necessary to have this codification early on, as conversations between small groups of individuals completely sufficed in getting alignment, at scale, codification became important to collaborate effectively across large groups of people. And again, this was scary for the organization as teams and individuals had been so used to complete freedom around how work would get done or decisions would get made. And this meant that many folks needed to change approaches that had come to feel quite comfortable. But ultimately, by writing down roles and responsibilities, processes, strategies, we were able to streamline the workflow of the organization to better ensure efficiency. At a small scale, individual agency can come from fluidity but at a larger scale, the clarification of roles and processes creates coherence and can enable agency to thrive again. And our final lesson is to identify single points of accountability. By 2016, our product portfolio was growing and we had expanded into selling domains and brought in an additional product leader with deep expertise in domains to co-lead product together with me. Over the following years, I assumed I assumed various roles and responsibilities for different parts of our product portfolio and also we also acquired products like appointment scheduling and social media content creation tools that brought in additional product leaders into our organization. We all reported to the CEO and while we worked well together, the complexity of our product portfolio grew and as the buck didn't stop with any one product leader, we became organizationally fragmented. We had two heads of customer operations oh, sorry, this fragmented leadership had also existed in commerce and in other parts of the organization as well. We had had two heads of customer operations. Marketing as well was split across multiple leaders and so forth. This was a remnant of earlier days of our company when having a flatter organization that wasn't hierarchical actually helped foster our earlier success. But as we grew, we needed a cohesive product strategy under one product leader that had at its core a vision for optimizing our organizational success. By 2020, it became really clear that having a single point of leadership and therefore accountability for coherence was critical at our scale. By now, we were well over a thousand employees and had millions of subscribers. We had already successfully centralized customer operations under one leader as well as marketing under one leader and it became clear that we should do the same in product as well. We were also preparing to go public and there was public company experience that we lacked on our leadership team at the time. This became another molting moment for us as we moved from having multiple product leaders reporting to the CEO to hiring a chief product officer to lead all of product. And again, this was another scary moment for the organization, for everyone. Our CEO Anthony had led product up until this point and this organizational change was a really big one but it was so necessary and ended up being not only great for the organization but also for each of us as product leaders. You see, with the CPO in place, I was freed up to bring my undistracted attention back to commerce. By this point, commerce was generating over $150 million in annual recurring revenue was the fastest growing part of our company and I wanted to align myself with the greatest opportunity to drive overall business value. Commerce had the potential to become the core part of our company strategy and here was my chance to return to earlier lessons learned, specifically narrowing scope to grow. I relinquished responsibilities for parts of the product portfolio that distracted me from the school and I molted yet again to take on a new role as the VP for all of our commerce offerings. The impact on the company has been palpable. If you listen to our earnings calls, you'll now hear our CEO talk about how the future of the company is being driven by sellers and how much they sell on our platform. We launched a marketing repositioning last autumn, one that gives you everything to sell anything and all of our teams, not just the commerce ones are now gold to think about the seller and their success. This strategic focus has been meaningful not only for the Squarespace business but has also been the most rewarding part of my career so far. Narrowing my scope back to commerce enabled me to have a more outsized influence on our company strategy and drive business impact and it also helped me grow so much as a leader and as an operator. Returning to lesson one, narrow scope and go deep to grow. Both for the company and as an individual, here again was another example that growth doesn't always come linearly and it doesn't always come from taking on more breadth. When as an individual, you align yourself with creating value for the company and a company aligns itself with creating value for its customers, good things will follow. That has proven as true in this chapter of growth as a public company as it was in earlier stages of growth as a startup. In conclusion, I want to go back to the idea of melting. I think the reason that that metaphor so resonated for me is that it represents the coincidence of vulnerability and opportunity. Just at that moment when one of those crustaceans sheds its shell in a moment when the future looms with uncertainty, that same creature grows a bigger, better shell and strength and endurance emerge. Over these 10 years that I have been at Squarespace, I have certainly molted several times just as the organization has. There were certainly moments of unsettling fear and surely of uncertainty, but I learned to see each as a chance for growth. Every stage, every shell helped me get to where I am today. Every level of organizational development, every challenge, every new approach contributed to where the company is today. And over these years, I've deeply internalized these lessons as I saw them repeated over and over again. If I can leave you with one thing today, it's that I hope that you do what I have learned to do over these years. To remember that whatever change you might be going through, or whatever evolution your company might be going through, there's an opportunity in it, both for your company and for you. If you approach it with curiosity, rather than fear, opportunities can abound. And in doing so, I'll bet that you get to the next step, the next structure, the next shell, faster and more effectively. Internalize whatever lessons you learn along the way and they will become a part of your toolkit that you will use over and over again. Thank you so much.