Birthday Week 2024: Behind-the-scenes with Project Management

Hello everyone and welcome to This Week in Net. This is the second episode with a behind the scenes look at our Birthday Week 2024 that took place in late September. For the first episode of this week, we had Cary Linder, one of our artists talking about art, and design for Birthday Week. And now we have Reagan Russell, Senior Manager and Program Manager responsible for most of the logistics of Birthday Week. Hello, Reagan. How are you? Great. Great. How are you? Thank you for having me. Welcome to the show. For those who don't know, where are you based? I am in Austin, Texas, and I'm actually in our Austin office right now. I'm in our Lisbon office, taking the benefits of our amazing offices, for sure. Yeah. Birthday Week was last week. For those who don't know, our Birthday Week is one of our innovation weeks, our main one, full of announcements, different products, different areas. This is a big effort throughout the company from different teams, putting together not only the products and then the blog posts that explain the products and the new tools, the new additions. It's a very big job in terms of having all of those elements, different teams together. For those who don't know, how does the process work and your involvement in that process? Yeah. So this is actually the third Birthday Week that I've worked on since I've been at Cloudflare. I'm a program manager by day, and typically I work on product development lifecycle, working with engineering and product teams to get products out and big programs that we have there. But for innovation weeks, there's a lot of project management and program management that has to happen. Everything from very early on, the ideation, what are we going to announce? Who's going to write the blog post? What other marketing needs do we have? How do we want to inform the media, the community, our analysts? So it's a lot of organization that takes place and a lot of cross-functional work that goes on behind the scenes too. When does it start specifically? For example, of course, when Birthday Week started, the company was much smaller. It was a different process, of course. Not that many teams, but in the past few years, the company has become larger, bigger. And with that process, it's really important. When does that start specifically? Yeah. So honestly, we've gotten a little bit better and better with this process all the time. And really, we're starting Birthday Week 2025 next week, having our retrospective and what do we want to do different next year? Of course, it doesn't mean we're spending 24-7 planning Birthday Week 2025 starting next week. But we really want to start with our ideas all year long. What do we want to announce for Birthday Week? The product managers definitely take a purposeful look in the quarters leading up to Birthday Week when they're doing annual and quarterly planning of what do I want to announce as part of Birthday Week? Like you said earlier, it's all about how we're giving back to the community, how we're giving back to the Internet. What gifts do I want to give? So when they're planning their roadmaps for the year, they're really starting to think about Birthday Week that early on. As far as when we kind of put the team together, assign the different folks that are going to own each of our coordinate, each of the work streams, we usually start that about five months in advance. But we're always thinking, we're always ideating on what we're going to announce for Birthday Week. I recorded a segment last week, Matthew here in the Lisbon office, about many topics, Birthday Week, how that started. But one of the things we talked about was the process of selecting what goes into a Birthday Week, what type of products we really want. He explained the relation with customers and feedback, different teams, what we want to give back to the Internet as a principle of Birthday Week. In that process and on your side, working with product managers, but even with different teams, director of engineering and all that, how is, and also leadership, how is that process of the decision making and finalizing at least the topics and features we really want from your side? I'd say the first Birthday Week that I worked on, one of the most surprising things to me was how involved our leaders are, Matthew, Dane, JGC, Neton, Grant, in Birthday Week and all of our innovation weeks. They really try to take a customer point of view, like, is this going to be interesting? Is this really giving back to the community? This might be a great thing we should definitely build and we should definitely launch, but is this Birthday Week material? They also bring great ideas to the table. They're not just prioritizing. They have these great, audacious ideas of like, hey, this is something I feel like we've always wanted to do at Cloudflare and the time is right because we have the right people or we have the right infrastructure or we have the right partnership right now. So it really is a great opportunity for not just the Birthday Week team, but all the product managers across Cloudflare to get ideas out and actually get to brainstorm directly with our leaders on what makes a great announcement. Makes sense. And it's quite interesting to see. One of the things that surprised me always in these types of innovation weeks, but Birthday Week is definitely one of those that resonates even more because it's different products, different areas of the company. To be honest, there's a lot of folks that don't know a lot about Cloudflare that are surprised when I say we had this day that we only talked about developers and our developers platform. Oh, we have a developers platform. And we have this day where we only talk about partnerships or free customers or new project Alexandria specifically. So we have different elements as a company. And it's quite interesting to see that those elements go into each day of the week. But my question for you is, how is those days put together in terms of making it really valuable on specific days for specific areas? Yeah. So that's a big role of each innovation week. We have a product manager that's kind of championing across all the different products and representing product. And between the product manager, the product marketing manager, and our communications team, one of the things we like to think of is like, how do we bubble up a message that sticks? Like, for example, when we have our developer day, how do we bubble up the message that this is the platform for all your developer needs. And that would be a combination of announcements, whether those are GA announcements, or maybe it's a beta announcement or an early access announcement. It could be technical blog posts, maybe something that we've launched, but people don't realize that you can use this product in various different ways. So we actually give tutorials and technical blogs on how you can do this. But really, that's kind of the thought process is what message do we want our customers or really anyone on the Internet to take away with the announcements of the day. And that's how we like to kind of group things together, kind of bubbling up a big message that's going to stick. Makes sense. You spoke about five months as the job increases in terms of needs, of things, processes that have to be in place. How is that process like in terms of blog posts that must be ready, folks that need to review them sometimes from specific teams, and then more generally, even leadership sometimes? How is that process put together in terms of creating the deadlines, but also challenges that occur? How is that process? Yeah, yeah. You know, it's kind of like any project or program, you kind of do a high level work breakdown structure. And we've done it so many times now, we actually have a playbook, so we don't have to do that from scratch every time. But it really starts with the ideation. And when we land on, okay, these are the big things we want to announce. What do we need? What teams do we need to help support this? And that could be anything from, you know, marketing team and landing pages, you know, maybe emails and other types of communications. I know you spoke about how you talk to Carrie. What visual assets do we need, whether those are for the blog post itself or even in product assets that we need for this or for what we're announcing. And so really kind of thinking if we want this message to land, what support do we need? And then rounding up coordinators across all those different areas. And it's actually really fun because typically I work mostly with product and engineering on most of the projects that I launch. But when it comes to an innovation week, I get to work across marketing, sales, communications, product design, all of these teams across Cloudflare. And we're all kind of coming together for one common goal. And that is, you know, what are we going to do? How are we going to give back to the community and how are we going to help as a company build a better Internet? So it's a lot of coordination. It's a lot of work, but it's also super fulfilling to be able to work, you know, outside of just your regular working group comfort zone, work across the whole company. I mean, you and I have even worked together on innovation weeks, right? One thing that surprised me, to be honest, is there's this element of you need teams to collaborate. Some teams collaborate almost immediately. Others potentially is something different. Authors are different from each other. In the meetings I've been with you, one of the things that I feel is there's this element of this is fun. Let's make it this fun. Let's let's follow the process. Let's do this well and right. But let's also make this fun in terms of this doesn't have to be something loom or difficult. It could be something that we enjoy doing. Right. And you bring that spirit to those meetings, which I think is quite relevant and interesting. Yeah. Yeah. I hope so. That's what I try to do because it is fun for me. And to kind of when you're bringing that large of a group together and in asking people to do things a little bit outside their normal comfort zone, like you have to make it fun. Right. And also just keeping that end goal in mind of why are we doing this? What's the purpose of what we're doing and how are each of you kind of contributing to that overall goal and purpose? So we have weekly meetings, as you know, with all of our contributors and all of our coordinators. And we make sure to make those very goal focused so that folks know this is important work that we're doing and to to get excited and stay excited about the end goal there. Working with different teams, what lessons did you learn from the past few years, three years that you're doing this specifically in terms of different contributions from different teams can be sometimes a good collaborative effort, but also there's challenges sometimes. Sometimes someone has to make a decision. Right. How is that decision making? Let's follow through. Let's advance what we need to advance process like. Yeah, I'd say the biggest types of decisions we have to make is make sure that everyone understands what the priorities are and why we're doing what we're doing. And as a program manager, aside from that, it's also what obstacles can I help get out of your way so that you can help deliver on this message? And it could be really small things. It could be just maybe getting some operational support in to help them with their kind of day to day jobs, because we all have day jobs, right? Like nobody is like removed from their day job just to work on birthday week. But I think the biggest thing is just listening to people and hearing their ideas of of where they're maybe stuck and how they can get unstuck, how we can help. And and one thing that I think we've also gotten a lot better of is early planning and making sure that all these teams are accounting for the different innovations weeks we have, especially birthday week. It's always the same time of year. It's always the same week. Our birthday is September 27. So it should never be a surprise. But make sure that folks are planning for their teams and their project work around birthday week so that it doesn't feel like these are just last minute requests coming in. On that note, actually, with that comes a lot of process, a lot of early start working on these things. But as I know, as you know, there's unexpected things that happen, something that happened and we must react to have that in a product potentially. How does the unexpected work in terms of accommodate things or changing things? Yeah. So we talked earlier how we have these brainstorming sessions, right? And we have great ideas early on. But then the thing about innovative ideas, they don't always come five months in advance, right? Sometimes we have a great idea that comes a few weeks before birthday week. And one of the things I've been so impressed with at Cloudflare is just the level of innovation and ownership that teams take when this happens. And it's not a matter of us having to convince the teams. It's the teams themselves that are usually bringing these great ideas. And they're like, how can we make this happen? I think a great example of that is the research team might be working on something and they're like, hey, this is actually a really great announcement for birthday week. I know we're only three weeks away, but can we fit this in? And we had to talk to our product managers about it. We talked to our leaders about it and they'll say, yeah, this is a really great idea. We should fit this into birthday week. And so that's why we bring it up with our coordinators. And that's why we have a plan in place. We have a plan in place that is agile enough that if things change, we can kind of flex and fluctuate. And the point is, we want to deliver the most important things and everyone knows that. And so I think it's kind of built in. If you're part of birthday week, you're going to be flexible, too. And we don't stifle innovation by saying, sorry, we didn't plan that five months ago. We're not going to do it. If a great idea comes in, we're going to figure out a way to share it with the world. Makes perfect sense. And to be honest, I've been surprised many times seeing that happening, like making if a great idea appears, that takes like sometimes a big push from the from different teams, actually, sometimes. And if it's a great idea and folks can realize, oh, this is really interesting, this would be wonderful to have. You can see like a team effort of, hey, let's make this happen. We can do this. So that resonates in terms of drive, motivation. I really enjoy how those great ideas that appear sometimes close to the date. I'm so impressed with how self-motivated our teams are, right? They're like, it's not like, how can you make this happen for me? It's like, this is my idea. This is how I think I can make this happen. Can you help? So it's really amazing. I was, let me share here my screen, you were mentioning the Clawflare .com birthday week hub, it has all of the updates, announcements, blog posts, a short reference to them. This is one of the things that is done, like a hub for where people can see Clawflare TV segments about the specific episodes, press releases, and also relevant past birthday weeks. Do you have a favorite? We're showing all the blog posts, do you have a favorite announcement from our birthday week 2024? From birthday week 2024, that's a great question. I mean, it's really hard to pick which of your children are your favorite. I will say I always really liked the founder's letter because it's kind of that voice of Matthew and Michelle speaking directly to the whole community, which is internal and external. Like I read that and it's almost like a great like recap of my year as I'm reading what he's talking about. I remember all the things we've worked on as a team over the last year, and I feel like it's the best way to really introduce the week. Also, Sam's announcement, the AI audit, I thought that was a great, really exciting announcement, very timely with everything that's going on in the world. And then also, I know like a lot of our fan favorites are very technical blog posts and more of our how-to blog posts. And those are the ones that get lots of questions and lots of excitement in the community. So I don't know, they all have kind of a little bit of a different message and they all, there's something for everyone. It's like such a great buffet of options for folks to read about on birthday week. But those are some of my favorites. Makes sense. Actually, you were mentioning technical ones, this zero latency SQLite storage in every durable object. I was surprised on folks commenting not only in excitement about this, but, oh, I didn't know this was possible. So sometimes it's good to see surprises in some of our announcements and blog posts, for sure. Exactly. And the same thing with the Cloudflare TV segments. I will say that there is a builder episode of Cloudflare TV on Thursday that was really, really awesome. Rita was in it as well as Craig Dennis. And they were talking about all the great things that we launched for our developer community on Thursday. And it's a great recap, but then it's not just talking. It's actually showing and very interactive. I think the segment was an hour. We actually had a session in our Austin office where we watched it together. Yeah, it was definitely great. And there were, you were mentioning that we had in our Austin office, Builder's Day with developers there, also in the Lisbon office, London. There was a bunch of places on Thursday doing that. You were also involved in some of the office gathering, in this case in Austin, right? Yeah, yeah. And in addition to being a program manager, I'm also the site lead for our Austin office and partnered with some folks from our events team and our marketing team to put on birthday parties that were open not just to our employees, but also externally to the community. And so we had about 200 people in our office celebrating Cloudflare. Michelle actually came in and Mark and many of our other leaders from other places in the world. And we got to talk to customers, developers, some of our new partnerships that we made they came into. And it was really just a fun night of networking and sharing stories, talking about the announcements, especially all the exciting ones that were announced on Thursday. And one of the questions that I got at the party that I specifically remember, because people ask me every year, like, gosh, it seems like a lot of work. What do you enjoy most about the week? And I always answer it the same. It's just getting to work with people across the company that I normally would not get a chance to work with and kind of understanding how their processes work, what their teams are made out of, how they're similar to us, how they might be different to us, what their end all goals are. It's just it's just a great time to be able to network and understand what our different functions are at Cloudflare. There's also a global element, right, because it's not only U.S. based, it's Europe based, there's folks from Asia, there's folks from different places. Yeah. And it's been amazing this year. Shelly, who is on my team, Shelly Jones, she's a program manager. She's actually in the U .K. and we partnered on on launching birthday week from a program management perspective. And it was just great because as I was going to sleep, she was kind of like waking up a few hours later and getting everything going. Right. And so it's like we had round the clock coverage and support for all of our global teams. And you mentioned product managers, Brandon, that was our product manager of the week. He went to London to to have like more time in the morning, in a sense, because of the time zone. Also during birthday week, which was interesting, actually. I think he went to London so he could be part of the U.K. birthday week celebration. But I'm sure part of that was so he could support after hours that we had Brendan and Kelly, who were typically both of them are in the SF office, but they did do that kind of splitting up and dividing and conquering. So we had a product manager available to us pretty much 24-7. I'll have to say it doesn't matter what time zone Brendan's in, he's always working and he's always available. So it was great to have him close to Shelly, but he's always available. He's great. And now he should be sleeping in terms of the week after taking some rest and you too potentially. These weeks are really heavy in terms of of being available, of dealing with the changes and all that in terms of work, right? Yeah. Yeah, it is. I would actually say the week leading up to the week is probably the busiest. And then once we have all the decisions in place and once we have everything ready, it's just a matter of hitting the go button and letting our blog team do their thing and get things out and publish, letting our marketing teams do their thing and getting landing pages out and publish. Same thing with Cloudflare TV. So it's actually probably most hectic the week or two leading up. And then the week of, we actually get to be able to relax a little bit, except we had a lot of parties. So relax slash party. Actually, on that note, how was it like to deal with the deadlines on those weeks and pressure the blog authors? How is that like? You know, I think that that everyone's trying to add a little bit of like one more thing to make their blog post even better, or maybe they get feedback from someone and they need to to make it better. One of the things we did this year to move that earlier in the process is having earlier reviews and then also doing peer reviews, letting different folks from maybe other product areas, engineers, even JGC and sometimes even Dane will review blogs very early and give feedback so that they can make adjustments. We also had demo. Did you see John Graham-Cumming, our CDO and leads our emerging technology team. Yep. Yep. And we also did something a little different where we did demos for both Dane and John of this is something we plan on announcing at birthday week. And we want to show you how it's going to work. And that's really important to both of them. We don't want to just announce a bunch of ideas. We want to make sure that these that these products are really landing with the community and make sure that it's something that developers really need and are going to use. Makes sense. It's been interesting to see the process there. Last but not least, and I enjoy doing this question sometimes, anything about Cloudflare that your job during birthday weeks taught you in a sense that most folks don't know, but they should? I would say that Cloudflare is a very flat organization. And when I say that, I mean, anybody is willing to help you. I even Sunday morning before the founder's letter went out, reached out. And I know you did too, to Matthew himself and said, hey, is this is this blog ready? Is there anything you need, any help that you need from me, anything you need from Gary? And he responds back right away, right? Like, no, we're all set, all's a go. And I think that most of our leaders are very are very humble and they really want to be servant leaders and help. And so I didn't really truly understand that until I worked on Innovation Weeks, that they're rolling up their sleeves and they're getting dirty. They're reviewing code. They're reviewing blog posts. They they are involved. They're not just sitting up at their desk and and getting updates from me. And I had no idea how involved even our founders are with Innovation Weeks until I ran one myself. Makes sense, makes sense. Thank you so much, Regan. And that's our show. All right. Thank you so much. And that's a wrap.