Delivery Management at Cloudflare

Hello, everybody. Thank you so much for joining us here today on Cloudflare TV for our segment of delivery management and what it is to work with delivery managers here at Cloudflare. I'm Alex. I am the lead delivery manager for Europe. And today, I am joined by my colleague, Shelley Jones, who is actually quite new to Cloudflare. She's recently joined as a delivery manager in our team. Hi, Shelley, how are you? Hi, thanks, Alex. I'm Shelley, and I have recently joined Cloudflare as a delivery manager. If I ever simplify without diminishing what we do, I guess delivery management is a supportive function. We primarily work with engineering teams, and our aim is to drive efficiencies through the team that we work with. And for me, that's working with the Quicksilver team and looking at our processes and adapting those to foster a more efficient working methodology. It influences how we do our work and what we can achieve, and obviously without costing anyone sanity. Yeah, and you mentioned efficiency, Shelley, and that's totally right. In previous segments that I've done with some of our other colleagues and even externals talking about delivery management, we mainly focused on teams that we're working with, with product, with customers. So can you talk to us a little bit more about what the Quicksilver team does in Cloudflare within the engineering team? Sure, I guess every time a customer makes a configuration change, whether it's to their DNS or as a worker, we or Quicksilver distribute those changes to where we operate hardware. It's about 200 cities across 90 countries, and we do that within seconds. So the system we work on needs to be really fast. And also absolutely reliable. And it also needs to scale. So I think about 26 million Internet properties depend on it, and that will most likely grow. There's nine of us in the team, including myself, and they're all absolutely brilliant. That's great to hear, and I'm hoping that they're watching this. So before we go deeper into the work that you do day to day with the Quicksilver team and with Cloudflare in general, Shelley, why don't we take a step back and take a look at what's your background? So what brought you here? What steps did you take in your journey? I actually wanted to be a journalist, specifically a war correspondent. Don't ask me why. But I went off and I studied journalism. After I graduated, I got my first job producing entertainment content for an online-based Australian media company, which was also half owned by Microsoft. And it wasn't what I expected at all. There was some writing involved and it was pretty much a data administration job, but it wasn't bad. And it sounds really basic now, excuse me, but at the time it was really exciting. The team I worked in developed a custom CMS and it aggregated and syndicated entertainment metadata to most of Australia's national publications and mobile phone carriers. That's when mobile phone networks had their own mobile sites. It was a thing. And we also helped launch Foxtel's digital television service through their EPG, which was basically introducing customers to an electronic TV guide on their actual TV, rather than having to buy a physical paper or magazine guide. And it sounds, it was quite exciting. And I mean, it sounds lame to be excited by it, but I grew up in country New South Wales in Australia and I had pretty much no exposure to tech beyond Nokia 3310. So it was definitely an eye -opening experience for me. And I really did love it. I didn't end up pursuing journalism. I looked for any job that had the word digital in it because at the time there weren't defined titles, you know, titles like project manager. It was still reserved for roles in IT or civil engineering and delivery management didn't exist at the time either. Yeah. And actually you're right that I've seen so many similar jobs as what we define as a delivery manager, but with such diverse titles. And going back to what you were saying that your background, well, your educational background, let's say is very different. So you wanted to be a journalist. I, for example, also wanted to work in a similar environment. So I wanted to do PR, particularly political PR. So I ended up as one of the first things I did to write a column on a marketing, well, let's call it a digital magazine. It was called basic marketing. I was writing the public relations trends and things like that. Like I can't even remember who that person was anymore, because it's a long journey to come into that. And I wanna go back to what you were saying that like you slowly wanted to move into anything that was digital, right? So you clearly saw opportunity there. So how did you bridge that gap? Like what were the next steps that you actually took? It was a big step. I ended up moving across the country. So I moved from Sydney to Perth. And I mean, I followed a boyfriend at the time, which was also stupid, but you know, a thing to do. But the tech industry there was, it was pretty much non-existent. And the most exposure that I thought I could get was by joining an agency. And so back then, agencies were predominantly, I guess, advertising agencies and marketing agencies. They'd specialize in things like print, radio, TV ads, but with the evolution of tech and digital, so did they, they expanded their, I guess, product offering to customers to include digital consultancy services. So it would range from little display advertising campaigns to huge digital transformation programs. So replatforming legacy systems and infrastructure, as well as overhauling customer experience journeys and moving from calling themselves, I guess, advertising agencies to now what you will probably hear as experience agencies. I see. So not even digital agencies, but more experience and then it's the all -encompassing structure, yeah. So yeah, I will fully confess that when you say agency, I still kind of think of advertising agencies or maybe a digital agency of some sort, but it sounds very much like in some of your previous roles, you worked really closely with your customers, right? And it sounds like you had a lot of custom-made projects and tailored those experiences for them. So how did you find transitioning from an environment like that into Cloudflare where basically we are a deep tech company working on our own products that serve an entire market? So how did you find that transition, Shelley? It was interesting. I mean, I did work in a few agencies here in London before coming to Cloudflare. And even though in those agencies, I did work really closely with software developers and engineers, I didn't necessarily belong with that team. So in terms of like the company structure, you weren't embedded within that team at all. I think there's also a different culture within agencies. So they operate differently and they have different objectives. And the definition of success, I think is also quite different. And that tends to influence the working culture within teams. In agencies, traditionally, everything's around revenue, which is fine. We still deliver what we need to, but that's what it boils down to. And coming on board with the Cloudflare team, it was pretty exciting. And also, it was very reassuring. I knew there'd be an onboarding process, but I didn't expect it to be as sophisticated as it was. So new starters coming into Cloudflare are grouped together, I guess, in classes, like a graduating class, and the week is planned meticulously. Everything is super considered, not just the planning, but the content of what we learn too. So we have induction sessions with various teams across the business. And then both Michelle, who's the co -founder, president, and COO, and Matthew, the CEO, speak with us. And I think Michelle's session is pretty brilliant. It outlines how all the teams you've spoken with throughout the week actually fit together. So coming into Cloudflare, I feel like it was a bit of a soft introduction, but a good one. And I can relate to that very much. So if I reflect back to my own onboarding, and both you and I actually onboarded all remotely during this interesting year, that was 2020. So, and 2021 continuing, right? So it's true that we had this very structured week in which we would go over and try to understand much more about the business, the company itself, the people, the culture, how we make decisions, who are our customers, so on and so forth, even before we actually meet the teams that we work with. And I remember I didn't really meet my manager for a one-to-one session for the first five days, which in any other company that I've experienced would have been the total opposite, right? So I'm glad that actually you had a similar experience with onboarding. And I really think that we try to make sure that people understand the basics of Cloudflare before they step into their roles, because it's such an important part of our culture that we want to keep perpetuating after we start working the day-to-day. So you've completed your onboarding and I'm certain that you're still learning. I'm also still learning every day, to be fair. There's never a sense of completion in that sense. But I wanted to ask you something else, Shelley. So stepping back, so you had experience in various agencies, different customers, and now you talk to us a little bit about what Quicksilver team does. And obviously this is a team that supports other engineering teams in Cloudflare. So how does that work for you as a delivery manager, supporting an internal engineering team rather than a product engineering team? I mean, it's been great so far. And I think while we're not a product team, we still do operate in a similar way. We don't necessarily have direct customer feedback, but our colleagues fulfill that role, essentially. You know, if something's needed or it potentially doesn't work the way that it's expected, they'll simply reach out to us directly. And it's really beneficial because we can, you know, we have the luxury of being able to work with them pretty closely and as we need to deliver what's required. And, you know, even though we don't interface with customers, what we work on and what we deliver is behind the scenes there somewhere. Yeah, and ultimately at the end of the day, you still have customers. They're just internal, you know? They're employed by the same company. Exactly. Yeah. So if you think of your role and not just at Cloudflare, but think of, you know, how you built your career to bring you to a delivery manager role here, what would you say is the more challenging aspect of it? Ooh, that's a good one. I think for me, I probably don't feel it anymore, but only recently. I think not being an engineer, you know, there's sometimes I think I need to know everything, but it's not the case and it's not possible. So, you know, I'd love to know everything and I'll continue to learn, you know, anything I don't know. But in our role, we work very closely with a team, an engineering team and an engineering manager and their roles are to know. And so we complement each other well, like that allows us both to focus on what we need to. I think that makes us more effective as a team as well. If, you know, you don't need to know everything because someone else does. And, you know, I like what you said in the term you use that you complement the engineering manager well, because actually I think this is the role, right? You will have teams in which maybe they have all of the resources they need and everybody has a very clear view of what is expected of them, but there will always be gaps to fill. And the role of the delivery manager, as I see it, is not to make engineering decisions or technical decisions because this is why we employ the engineers, right? But I understand this feeling that maybe in some situations it would be easier if, you know, I held the engineering degree and if I had worked as an engineer myself and, you know, one way that I bridged that gap is always reminding myself that actually we do have colleagues who are self-taught engineers, right? So they didn't go to computer science universities, and they didn't study officially. And actually that's what I think is one of the great things about this team. And I'm pretty sure that it's the case in many and more and more companies that you don't need the academical credentials in order to be able to do a good job, right? So we're talking about learning constantly and knowing everything and teaching yourself or learning from others. And I think that that's really, really valuable ultimately because that's how we bridge those gaps, right? Yeah. So thinking back at your experience again, you talked about how you came to be a delivery manager. So far, I think you're doing a really good job at it. So what do you think differentiates, you know, a good delivery manager and a great? Ooh, I think, where to start? I think there's a few things that probably come to mind. I think you need to have initiative. You have to be a pretty skilled communicator. Obviously have a bit of empathy, but probably one of the most important things is having like a fearlessness when it comes to the unknown. I think, you know, our intuition, you know, we'll wanna know everything. We'll wanna control every aspect of a project or a situation, but I think it's the ability to accept and I guess roll with that uncertainty. And I think it reflects the level of great versus good. And I think, you know, if you can show how you add value, that doesn't hurt either, but definitely being able to accept uncertainty. I see, yeah. And I like this term of fearlessness that you mentioned. And I think we're on the same page here because I call it managing uncertainty. I really think that this is one of the best lessons that I've learned in my career and in this journey. And just accepting the fact that you can't always know everything. And that's okay. That's perfectly okay because the answer is there. You just need to find it. And coming back to what you were saying about the instinct is to want to control everything, you know, to have that feeling of security and of certainty. Well, that's not realistic. So we might as well say it out loud and move on, right? So this managing of uncertainty definitely has been one of my best allies in doing the delivery management work. And even more so with Cloudflare because it's such a big environment. And we have so many teams working with various technologies, always innovating, always putting out new features for new customers and different approaches to work. So I don't know if it's sane to think that at one point you will be able to grasp all of that, right? And if you do, then what's the beauty of it? Exactly. Sorry, I tell myself. Good. So Shelley, we talked about your experience. We talked about what differentiates a good delivery manager from an even better one. Let's say if we have some of our viewers who might be curious about this role or who might maybe be shy about trying it, what would be your recommendations for somebody who is considering such a role regardless of their background, definitely? Ooh, I think just go for it. Try it. I mean, you don't know if you don't try, I think. And if you begin to suffer from imposter syndrome like I very much did at the beginning of my career, or if you have that self-doubt, just ignore it and carry on. That sounds easier said than done, but I think it's one of the biggest challenges that you'll probably face is like your own challenges. And I think, you know, learning, reflect and learn from your experiences today. I think no one ever starts in a role as an expert. And I think one of the biggest misconceptions around making mistakes, especially if you're just starting your journey or your career, is that it's your fault. And the feeling that you get as a result, sometimes it makes you wanna give up and just not try. But it's when you make those mistakes it's probably most likely a result of a particular, you know, support or system or structure kind of not being there for you, whether it's a process or people. And it's easy for me to say now, but a decade ago, I would not have even considered that. But if you can identify those things and learn from it, I think you're already halfway there. Do the job. Yeah. Just, you know, try, don't give up, challenge yourself every opportunity that you can. Yeah, thank you for that. That sounds very, you know, encouraging and I think inspiring to be able to put together all of these thoughts, but also acknowledge what is unknown and what can go wrong. And that's perfectly okay. Like I have to keep reminding myself that it's okay. You know, make a mistake, you try something, it doesn't work out, try a different angle because ultimately there is a solution for everything. So Shelley, what would you say is the most surprising thing so far about the clouder? Ooh, lots of things. Probably autonomy. Okay. Okay, so this is interesting. Tell me a little bit more about what do you mean by autonomy and why is this surprising? So I think all teams are kind of, you know, they're self -managing. You know, we have the autonomy to progress things that we see fit and as we see fit. And I think it surprised me because I think at Cloudflare, it seems silly, but it seems like there's so much more at risk. In an agency environment, I guess, internal processes allow for everything to be managed pretty rigidly and robustly. And the risks encountered in that environment, I think they absolutely pale in comparison to what could be at stake here. And that's not to say those risks aren't important or that we don't manage risks at Cloudflare, we do. It's just that the potential impact could be so much greater. You know, like we could have an incident or an outage. And for whatever reason, I kind of attributed that to autonomy, but I don't think that's necessarily the case. I see, yeah, that's very interesting. And you do mention some of the risks and it's true. I mean, in no business, we wouldn't be able to have this business if we wouldn't acknowledge and embrace the risks and sometimes they happen, right? So can you talk to me a bit more about the risks? So what's risky about autonomy? Because obviously we see a lot of good things in it and definitely it means empowering the people who work here, but what is really risky and how would you think that this will evolve for a company like Cloudflare as we mature? Yeah, well, I think with autonomy, I just, I'd made the wrong assumption that, you know, with that came, well, risk. And I just thought that it wasn't managed, I guess, in like the sense of the experience that I was used to, like, you know, let's have a raid log or a risk log for all sorts of things. We still have those things, but I think my assumptions were just wrong. I mean, the teams are super experienced, they're skilled, they're dependable and everything they do is done with that risk in mind. So it's a shared responsibility and it isn't managed by a single or one single process, it's considered throughout. And I think it's that kind of maturity and mentality. I think it's throughout all of our teams that sets us up for success, you know, just because I can't see it written somewhere or, you know, it doesn't mean it's not considered, it is, it definitely is. Yeah, definitely. Yeah, I also believe that it's part of our fabric, right? So you don't need a written policy on this. To make it your, like your company's common sense. I think that this is how we operate, definitely. Right. And Shelley, I wanna go back to, cause we still have a few minutes left. I wanna go back to an idea that you mentioned earlier. You mentioned imposter syndrome, I think a couple of times. Recently, we've had a really, really good session with Amy Cuddy, who was talking about imposter syndrome as well. That session was part of Women's Flare, which is our Cloudflare employee resource group for women. I believe you're part of that and of Women in Engineering. What does that mean? Can you tell me a bit about your experience there and how are you finding it? Yeah, I mean, I am. And it's the first time I've ever been part of an ARG or an employee resource group at all. I think, you know, initially I did feel like an imposter being part of the Women in Engineering group because I'm not an engineer, but I am in the engineering team. But that's the whole point of the group. You do need to be within the engineering team. You also don't need to identify as a woman to join. It's, I mean, both and all of the groups, I guess, across Cloudflare, they're super inclusive. And I feel incredibly lucky to work within a company that supports and highly values just that. I mean, to have groups that specifically support, you know, your professional development and success within Cloudflare, I think that's so valuable and so important. And, you know, it's such a great thing for a company to, you know, put their money where their mouth is, sort of thing. Yeah. And it's actually, you've just quoted the mission statement of the Womenflare, right? It's to support women's professional development and success within Cloudflare. And we've seen, we have so many segments led by women from Cloudflare. Also one of our founders, Michelle, she leads this weekly session that is, well, segment that it's called Yes We Can, right? And it's interviewing a lot of successful women. And I personally find that really, really inspiring, exactly as you said. It's good to have access to the platform, to have the conversation and everything, but also the resources and the concrete actions that the leadership team, and the rest of Cloudflare actually, because it's not just top-down, right? It's taking to support different kinds of groups is quite inspiring. And I find it really, really important. And actually we're very much on theme with what is happening this month in international, today's International Women's Day. Also we have Women's Empowerment Month. So one of our themes and this year's Cloudflare theme for all the celebrations around International Women's Day, week or month, is it's called Choose to Challenge. I wanted to ask you Shelly, what does that mean for you personally, choose to challenge? That is a very good question. I think besides challenging, I guess, inequality and gender bias, which we should do every day, for me, it's probably preparing to be uncomfortable. So both when it comes to personal development, being involved in initiatives like this, that terrify me and also exposing myself to, I guess, concepts or things that I've not had an understanding of before. And also, I guess, having uncomfortable conversations with those closest to me. So whether it's to challenge ideas or even just hear about other's experiences. I mean, if I can't manage that, then I can't be part of change. Yeah, I like that. I like how it sounds. And thinking of choose to challenge, you talked a lot about yourself. And I've actually heard a lot of our colleagues and a lot of women in the cloud, they're saying, I wanna challenge myself and I wanna challenge my own thinking. And I must confess, when I first saw the hashtag, choose to challenge, I thought of, yeah, I wanna challenge the way that I see things, the way that I respond to things and the way that I react and I engage. And it made me think a little bit, hmm, maybe I should challenge others or lead very different conversations. But ultimately, it needs to be part of me because I can only control what I do, right? So for this month, I am putting a challenge for myself to speak up a little bit more maybe than I would have done otherwise. But also to push to learn various different things. So it sounds like we're looking at it from a very, very similar angle, Shelly. Shelly, we have about a minute left from this segment. So the floor is yours. Is there anything, any closing thoughts you might have for the audience or any question you might wanna leave them thinking about? Ooh, not too sure. I think mostly this has been such a great opportunity. I've never done anything like this before. And I think being on International Women's Day, it's pretty impressive. But I think it's also testament to Cloudflare's, I guess, commitment to, I guess, equality and inclusivity. And I think it's not just, and it doesn't just revolve around International Women's Day. I think we practice it and believe in it every day. So I think this has been really good fun. I'm really happy actually, Shelly, that you joined me. First of all, because I got to discover a few new things about you. So you mentioned that this was a little bit scary in the beginning and you haven't done something similar, but remember you wanted to be a journalist. So there you go, you had your chance. But also not just because I got to understand a little bit more about your background and how you work and everything, but it's always really interesting to connect with women with Cloudflare and beyond Cloudflare, obviously, who would share very similar thoughts and have these inspiring ideas for myself and for anybody who would be viewing us. So thank you so much, Shelly. Thanks, Alex.