Name: The Automation Advantage: How Chess.com Tripled Its Global Workforce with a 4 phase HR automation strategy
Uploaded: 2025-12-03T20:16:11.421Z
Duration: 1 h 4 s
Description: The Automation Advantage: How Chess.com Tripled Its Global Workforce with a 4 phase HR automation strategy

Transcript for "The Automation Advantage: How Chess.com Tripled Its Global Workforce with a 4 phase HR automation strategy": Hello, everyone. Welcome to the Automation Advantage. We're gonna be getting started shortly. In the meantime, feel free to put in the chat where you're calling from, and we're so excited to to be with you all today. We're just gonna give one more moment for folks to to join. So thank you all again. I see Emily is calling from Seattle. We have Melissa from Bellevue. Okay. So we're almost gonna get started. We're heading to almost two minutes here. Hope everyone is having a wonderful Wednesday. The rippling team here, we're calling from New York as well. Richard, hello. Hello, Zach. And, yes, we would love for you guys to be engaged here in the chat as you watch this conversation. So, if you have any questions for Brendan, please put it in the chat box. With that being said, we're gonna dive in. But before we get started with the conversation, we just wanna give a little overview of who we are here at Rippling. So just some housekeeping. The chat function on the corner is there to post any comments and connect with other attendees. If you are interested in Rippling, and to learn more about our HR platform, please book a demo with the button on your screen. As you might know, ripchest.com is one of our customers, and so we're so excited to be spotlighting Brandon here today. And this webinar will be recorded and shared with you as well tomorrow in case you wanna share it with your friends. And if you don't know who we are here at Rippling, well, our mission is to free smart people to work on hard problems, and we are one of the number one rated HCM platforms out there. And, our platform focuses on the employee graph, which serves as a single source of truth for workforce data. And so here at the Automation Advantage, we're showcasing the power of what our platform does for incredible customers like chess.com. And so with that being said, we're gonna get started, and we're gonna welcome Vanessa and Brandon to the stage. Thank you all again, and, stay tuned. Oh, hi, everyone. Thank you so much for watching, and we hope you enjoyed the surprise. It's us. And. time to answer some questions that people had. And we've gotten quite a few questions. And so, also, before we dive in, I just wanted to mention if you're interested in booking a demo for Rippling, please press the button in the poll. If you're interested in automating your workflows today and just like Brandon has done at chess.com. And with that being said, Brandon, if you wanna say anything before we dive into some questions we got from the crew. Yeah. It was really great to to connect and talk through all of this, and I see a lot of activity in the chat and a lot of interest, not just in automation and in Rippling, but also in chess, which is great. So, let me make my own pitch. Like, if you wanna play chess, come check us out on chess.com. You can find me. Brendan w is my username. Send me a challenge. Happy to play anybody. I bet you'll get more of a challenge than playing me. Okay. So I see that we had quite a few questions regarding, the global expansion, and so I thought that we could maybe start there. I guess we can combine two questions from Andrean and Jess, about how you were able to handle global payroll, and contractors in other countries, and also just maybe breaking down what countries CHESS team members are or chess.com's team members are in and, like, how Ripley was able to support having a global workforce. Yeah. Happy to talk about that. We have a very broad spectrum of team members all in different types of relationships from over 60 countries and so most of what we're paying out of rippling in global payroll are our countries where we have entities and so from the global currency standpoint we have a entity in The UK where we have UK payroll and we pay people in great British pounds. We have a Canadian entity where we're paying from a Canadian bank account in Canadian dollars. So we didn't run into any trouble with getting set up on local currencies as we we had businesses set up in those regions and we had banking set up in those regions. So we didn't find a lot of friction with that, but, you know, think thinking to the rest of our our relationships as well, you know, we don't have the longest list of currencies that we kinda work in so, I'm kinda just reading the question as well like linking bank accounts to one company and a lot of FX change. We we don't encounter that because I think we're just working directly with our local entities in those places. Amazing. How I see one person asked, scaling without an IT team is a genuine challenge, and we're only at two fifty employees. The realities of day to day IT support and remote software management. Okay. Sorry. The reality. I find that HR teams are is the default IT. What tips or guidance would you have for think? our biggest wins came from automating, and it's a great a great question. Our biggest wins came from automating particularly the onboarding and offboarding process and trying to just get as many of our systems controlled via Rippling as sort of an identity provider as well not just a, not just an HRIS. And so we have things set up so that when someone gets hired we have countdowns to when their accounts will be provisioned, and they'll first get their email set up, and they'll have all of their invites waiting in there. We also have done deep integration on that so that if they join a certain team, they'll be added to either that team or that group or that permission set within the application. And so, for example, if you're hiring developers and you're using GitHub or Jira, you can set them up to be placed into the right permission groups so that on day one, there just really isn't any lift necessary there. Similarly, you know, if you if you have off boarding, if someone moves to another organization, you can coordinate all of this so it automatically off boards. And similarly, like, we're a a Google Workspace company. So if we're offboarding somebody and it's in Google Workspace, we can automatically give temporary provisioning to their manager to transfer files and all of that too. So a lot of the tasks that would be that would fall on our shoulders, we've tried to automate as much as possible. It Yes. It always comes back to automation. does. It really does. I think Jesse is curious about she's struggling with implementation. Was wondering how you were able to get all the information you needed, with such a lift to find administrative information. We're finding this to, the we're finding this all is falling via being able to pull from a payroll system. We implemented a long time ago, and so I think there's a big said a big portion of the answer for us specifically is that we were around a 100 or so head count at the time. And we had disparate systems, but we were able to pull together our best known information and and proceed with that. And because it was maybe a hundred, hundred and twenty headcount, if I remember correctly, that's manageable for a human to look at that list and validate that information and upload that. I think if we had to do that today and let's say we were 700 or a thousand people and we were on all these different systems that might be be more painful. But if I think about solving that, data integrity and cleanliness and consistency and formatting is your friend and yeah it is it is painful it is painful to pull all of that together but if you're pulling from multiple systems I don't. know that there's a great way to just automatically pull it all together. I think that. there is a little bit of work that has to happen up front to create your source of truth. and so you start there, you pull the information together, you get it into like columns, so that you're you're operating from one consistent dataset, and then you implement from there. Yeah. It's not like an overnight thing. It's still and that's with any type of implementation process. Yeah. Yeah. Absolutely. Galena do you see the question from Galena? Yeah. I just flipped back over to chat, and I saw that there's there's. conversation here too. So, If there was something your implementation interested experience, in. from day one through final phase, key phases of the journey, each phase was managed, and what resources. So, again, this kind of connects to the last one where my my very transparent honest answer is that, I joined chess.com just after it was initially implemented and we implemented at the 2019. And so Rippling as a company and a product and chess.com as a company were very, very different. And so the lift and the nature of implementation then was very different. Like, Ripline didn't have a talent stack. It didn't have a lot of the global features that existed today. It was global capable, but it wasn't really global integrated. And so sharing those phases, they don't really map to today's reality, unfortunately. You know, we had a, I think, a positive experience through that, but it would be hard for me to compare something from from six years ago now to what you're going through. And then Francis asked and and I hope that I I apologize that it doesn't give you the best answer, Jolina, but I I hope that that gives you some insight into what our experience was. Francis asked too about process of deciding what to switch to. And, again, the decision was made just before I joined. We've gone through a number of renewals with Rippling, obviously, and continue to to partner with Rippling and feel good about that relationship. The biggest thing initially was that as a very lean operation and, again, having disparate tools for our US employees versus our global contractor relationships and things that we were working on back then, really the few key things was a single source of truth so all of our information was in one place. And then it it felt again, it felt to me at the time that this was something disruptive and there wasn't a lot of this type of automation happening even in some of the administrative basics. So we were really excited about that and ended up moving forward with it. And then continuing just as we've renewed over the years, Rippling continues to expand how they're viewing the the back office and what tools they're offering. We continue to implement new modules as they come out and and fold our talent stack and information in there, fold our performance management, into Rippling as well and just find that having everything in a a single again, I I'll say this a 100 times, but having everything in a single source of truth just helps us make decisions faster. It helps us have consistent information, and then we spend more time trying to solve the actual problem instead of understand the problem. Mhmm. I think that kind of relates to as well to the someone asked about, when you, like, do your automations and you you automate a lot of processes, how do you, like, account for the human component, like an employee who receives an instruction but doesn't understand how to execute? I guess the human component is somewhere where you would have to spend time, like, solving that problem, but that's also a harder and more interesting problem to solve than, like, administrative work in a sense. So Absolutely. And it's really important to us as well. We don't we don't wanna replace the human element or the the human feeling of how we operate with cold automation. Right? That would just wanna do is automate yeah. What we wanna do is automate all of the prework to that moment. So sad. if you're gonna if you're gonna meet with somebody to talk about something, they have a question a question or a problem or something you're trying to solve whether it's for an individual or for a team or for the company, there's a lot of lifting that goes into that administratively, right. If you're in again non automated systems you need to go and pull a report or pull a census or pull this information and then evaluate and assess. And if instead you had just this, you know, digital assistant who had everything prepped for you and sent it to you just in time so that you just show up to that moment. fully briefed with all the information that you need, that seems like a better reality. You're still having that human moment, but you're having more of those human moments instead of Totally. as many as your calendar can handle because you need twenty minutes to research the thing before you have a fifteen minute conversation. Yeah. You can fit more human moments in a day. Totally. And that's, like, the most important piece of it all because at the end of the day, it's human resources. Like, we gotta put the human back. Heck. Yeah. Yeah. And whether you call it yeah. Human resources or, People system lot. of companies are are people. Right? Yeah. It's it's the most important part is the human part. That's the nuance. and the element of it that no amount of automation will replace. A 100%. And it's the most important part of any business, really, because without people, you don't have a business. Okay. Let's Here's a follow-up. This is a good follow-up. Needs resources. So if your HR team needs resources or guidance on setting up workflows, administrative tasks, processes, is there a resource library? Are there how to materials? This is a a great question. I think that depending on the size of the organization and the breadth of your organization, you may have slightly different experiences just to say that out loud. Like, you may have a different size of account team working with you. In our case, we're fortunate to work with a technical account manager who, if we have, you know, challenging questions or more technical questions that we need to work through, we can get support that way. We can work directly just with the general support team to learn information. Rippling also has a library, both a training library as well as a help center and content library where a lot of this stuff is talked about. And what was the other thing? Is there a community or is that had I I don't wanna we are actually in the process of we have a community, an HR community that we're building at Ripley, which is exciting, Okay. and it. just got launched. know if that was out or not out. it's like called we didn't know that. it, so it's like a baby community. But, hopefully, Okay. Gailita, I'm also, I'm apologies if I'm pronouncing your name wrong. But, hopefully, that community would also serve as a as a space where you'd able to learn more about automation for HR and get, like, actual examples of use cases from people like Brandon who have already kind of been in the weeds with it. Happy to share more information as well if you wanted to reach out. I can put my contact there in the chat. I I'm really excited about that piece in particular. I think that one of the things that I've witnessed is there's a lot of thought leadership out there in social media, but not a lot of actual sharing of resources or tactics. And I would love to share the things that we built. I would love to go and say, like, here's some stuff we made. What do you think? How could we improve it? What did you build? And. I think that if we were more willing to trade LEGO, that we could all We this out way faster. a 100%. Because it's like we there's not, like, one way to build. Also, I so previously on the automation advantage, we had Karen Wilkins from the guarantors. And something that was really interesting was just how she's been, like, iterating on all the workflows and automations that she's been building from, like, a year ago. So it's not like you automate a system or a workflow, and it's like, oh, I'm never gonna talk or see this again. No. It's like you can always find ways to make it even better. And so I think have the community will hopefully empower everyone to, like, learn from each other and constantly iterate because it's like a never ending kind of process, which is a good thing because there's always room to improve. But yeah. Agree. Agree. I think that's I'm caught up in chat. I'm scrolling. I don't see anything else. Another one. Oh, another one from This one's for you. I I don't know what Ripline's thinking is, there. what's Rippling's thinking? Are you agentic AI? Either as a platform or as a tool for clients? Are you reinforcing flywheel effect. We are actually, well, stay tuned for 2026. It's gonna be very exciting. We have some really, awesome announcements coming up about AI and how we're integrating AI into our platform. So there's gonna be a lot of opportunities there to delve into that, and, I think that Rippling does wanna be on the forefront of it. So I would say stay tuned for updates in 2026, but there is gonna be something around that for sure. I think there's a new question too. Yeah. Customer service related. I happy to happy to talk about that and just share again, share our personal experience with that. Typical response time so there's a few avenues to connect with support, with Rippling. There is a in platform AI driven chatbot, which can be generally useful if you're looking for surface level information or kinda, your your first troubleshooting steps on trying to work through something. I I find it to be fairly accurate most of the time and mostly useful. If that's not helpful for you and you need to reach out to support, you can either do it through the chatbot or through email directly in my experience. And, usually, if I'm going through email, I'll find a response within a couple of hours most of the time. If it's a really complicated or complex problem, it can be a little bit of a longer time line, but I usually find a pretty quick response by email. If I'm going through chat, I'm sure you guys have chat hours that are specific. I don't know what they are because whenever I'm on chat and I need help, somebody's usually available live, and I can turn my AI chat into a live chat. And if it is something particularly complex and we need to work through it in person, I've been able to get live video time with that agent fairly quickly. So, again, I don't wanna speak for the program details itself on Rippling's end and and exactly how those come together, but that's been my personal experience working with, with support. So that answers your question. Okay. There was one question that I thought was interesting too, and it's, like, not very rippling focused. It's more about your journey, Sure. and I thought we should we should kind of end it off on this note. So I guess reflecting this is from Daniel Ashton. So thank you, Daniel, for submitting, no. this question. Reflecting I know that guy. wait. What's is he he's from just.com? I believe he may be. Okay. Well, Daniel, if you are here, you're I'm asking your question for you, I guess. Reflecting on the wild last six years, what brings you joy today? And I guess just reflecting on your experience and all the work that you've done and the impact you've made, what what has brought you the most joy? I, I get a lot of joy, working with great people. And so, like, working on meaningful things, and building meaningful relationships and working with positive, like minded, really passionate people brings me a lot of joy, and that's where I take that from. I I still have a a lot of love for digging in on the automation, but the difference now, I'm really fortunate that in the first couple of years, there was a lot of digging in alone, or. quietly into some of these things. And now I have this this really, I had such great fortune to be able to dig into these problems with a team of incredible people, Daniel included. And so I I I just find so much joy in solving these problems together, and and I love doing that. Well, that's amazing. And yeah. I mean, I relate too. I think, like, automation is great. And the reason it's great is because at the end of the day, it leaves us to do the things that really, really matter, which is, like, the people stuff and focusing on making an impact on the people that you work with. So I'm sure you've done a lot of that at chess.com and that they're very lucky to have you. So, I hope I'll find out. I think there's a bunch of the team watching, so I'll get razzed appropriately, after. hello, But, chess team. there's there's one there's one last question that I'd love to answer in our last minute here and, near the start of it there's this really really profound question that was asked and the question was Chess And the answer to that question quite clearly is Chess. love it. Well, you heard it from Brandon himself. Thank you so much, Brandon, for doing this and for sharing your journey and your wisdom and your automation secrets with all of us. And thank you all for coming and watching today. We hope you enjoyed and learned something and hopefully start automating your HR systems and put time back to focus on the people. So with that being said, I think that concludes our our webinar. And, yeah. Thank you so much. Thank you for having me, Vanessa. Thank you everyone for all the questions now hope to connect with everybody again. I really believe in a future where we can share Yeah. details and and some of the things that help make our our lives better for us and our teams. So, I hope to help create that reality. I hope so too. And, also, I have to give a special shout out to Brandon. I don't know if you guys have watched our trailer, but oh my gosh. Last thirty seconds here. Brandon dressed up in an entire chest piece costume. If you haven't seen it, you have to check it out. Let me see if I can find it really quick, but this was by far the highlight of the webinar experience. I have it in two seconds. Can I upload it? But. yeah. Go. Go. Oh my gosh. Okay. That's it. Have a great Wednesday, everyone. Bye. Go. Thank you.