Everything You Need to Know About Remote Teams in 2025
Casey Bailey, CHRO at Deel, shares how a fully remote team across 110+ countries thrives on trust, autonomy, and hyper-localized strategies. She dives into intentional hiring, fair compensation, and building sustainable cultures while balancing global complexity.
In today’s episode of the HR Leaders Podcast, we welcome Casey Bailey, Head of People at Deel. Casey shares how Deel’s fully distributed team across 110+ countries thrives on trust, autonomy, and clarity.
She dives into the importance of intentional hiring, hyper-localized compensation, and building a strong company culture in a fully remote environment. Casey also explains how HR leaders can balance global complexity with empathy, empowering teams to work asynchronously while maintaining engagement and high performance.
🎓 In this episode, Casey discusses:
Managing compliance, onboarding, and cultural complexity at a global scale.
Practical strategies for avoiding burnout in an “always-on” remote work culture.
Why intentional hiring and clear company values are critical for remote team success.
The importance of hyper-localized compensation for ensuring fair and equitable pay globally.
Deel is the all-in-one payroll and HR platform for global teams.
Deel helps companies simplify every aspect of managing a workforce, from onboarding, compliance and performance management, to global payroll, HRIS and immigration support.
Deel works for full-time employees and independent contractors in more than 150 countries, compliantly.
And getting set up takes just a few minutes.
Casey Bailey 0:00
Deel. We've got people sitting across 110 countries. It's an always on. I'm always saying this is like a game of football, right? Like 24/7 365, you've got customers on the field, team members on the field. People are coming on and off, taking water breaks, going to the locker room. Something is always happening. And you're really having to trust people to come on and off. And I think when everybody works in that way, there's a lot of trust, empathy, respect for the time zones and for how people work. I think, obviously that's changed a lot since the pandemic as well, and more people going remote, but I think that's really helped me balance my family. I'm balancing my family better than I've ever balanced my family, I guess I would say in my career, because of this opportunity to work the way that we're able to work now.
Chris Rainey 0:53
Hey, Casey, welcome to the show. How are you? I'm well, how are you? I'm good. Nice to see you. Nice to see you. Before we jump in, tell everyone a little bit more about you personally and your journey to where we are now. Yeah,
Casey Bailey 1:07
so I have spent almost my entire career in the HR space. I was a failure at law school, so I came out of college. Was
Chris Rainey 1:19
your failure? Or did you realize it just wasn't for you? There's only two. That's true.
Casey Bailey 1:24
That's true. I was getting by. I could have remained at law school, let's say that I could have stayed there. Very hard conversation with my father that day to let him know I wouldn't be returning for the second year of law school. Yeah. So I opted out of law school and decided that wasn't the path for me, but really had a passion or an interest curiosity around the employment space. And you know, my mom spent her career in HR, she had no college degree and did a plethora of different jobs in our early days, like up until I was five years old, and then kind of fell into the HR space. Grew in that space through a bunch of different companies, actually growing with those companies, as they were acquired by other bigger companies. And because she was learning the craft, doing so well and being successful, those companies actually kept her and so for, you know, the Impressionist years of my life. You know, through specifically middle school, high school, she was in the HR space, building herself up to a chro into an HR executive, and ultimately worked for the largest company she ever worked for was AT and T Wireless globally, running their wireless division for HR. And so my sister and I actually are both in HR.
Chris Rainey 2:44
I need to get all three of you on the show. It's like generational HR right now. I love it exactly. Episode Title right there.
Casey Bailey 2:53
I love it, yes. So my mom is still in HR and benefits consulting space, even after she retired from at&t, she stayed in the space. She's active today, and my sister is a chro for F 45 so
Chris Rainey 3:08
what do you fitness? The fitness company, yeah, well, we're all in it. You're one of like, normally, when I asked that question is, like, we've over 1000 sitters have been on the show, maybe, like 20 chose this career, like, actually, from the early age or, you know, and normally, 99% of time it's because someone in the family was in HR, because very few people grow up saying, hey, I want to work in H
Casey Bailey 3:36
tackle, payroll. Yeah,
Chris Rainey 3:39
yeah. Wow. That is so I, like, your mom needs to write a book. Like, right? Like, like, That is incredible. Yeah, reading. HR, yeah, wow. I'd love to have, like, generally, no, it's not even a joke. At some point, I'd love to have you all on. Like, that'd be a really amazing episode. We need to set that up with you, your sister and your mom. That's so cool. Wow, you just threw me off there. I was not expecting that way. I'm gonna go off scripts a little bit now with some questions, because I have to ask you a couple of questions, what was the biggest, biggest lesson or learning that you took away from your mom that's helped you in your career?
Casey Bailey 4:20
Yeah, I think I mean, and I actually worked for her coming out of law school for a short time in consulting, and I think some of the best advice Shepard gave me, and you're working with people, right? You're working with people that count on you for their paycheck, or count on you for getting the right benefits, or count on you for getting an employment verification to go buy their first house, right? You're you're doing something for a human at the other end of the work that you're doing. And I think she took that so seriously, but also was like, this is a place where we can learn. We're curious how you do HR matters about where you're working. That. The work environment the founder or the executive team, the people that you're serving, looks different, maybe for healthcare than it does for manufacturing, than it does in a tech company. So always, I think, meeting people where they are and really understanding, developing that business acumen, right of being able to identify and take what you know and have learned, HR foundation wise, but be able to bring that to life for the environment that you're in, for those people, the day to day, right, the tactical behind the scenes, administrative work of HR even back then. I mean, when I started, right, I was in consulting for the first 11 years of my career, when HR business partnering was just kind of becoming popular, but she was also always very good about think about what you're doing. Don't just run what Sherm is telling you at that time or what whoever is telling you at that time. Really think about what you're doing for the business that you're serving. And I think that that has served me well in these times. She also would always say, if we haven't killed someone, we can fix it. If we have killed someone, it's just going to take a little bit longer to fix this. So very open to you know, we're going to make mistakes. Mistakes are going to be made, yeah? But how we handle them, it makes all the difference, right? Yeah.
Chris Rainey 6:12
This is so cool seeing your mom go through that process of obviously not having any formal education, working her way up through the ranks. You're seeing that at home, I'm sure, as well both sides. How hard she the work she put in. How has that shaped you as a leader?
Casey Bailey 6:31
I think Alex would probably say, I you know, I work. I work very hard. I take this job very seriously. And I think actually my mom and Alex, my current boss, are quite similar in this that the output that we're giving right is delivering something for a person. And I think because of that, I I take this role really seriously, and I take, you know, I I probably work too maybe I work too much, I don't know, but I'm always, I'm an always on personality, so, you know, I'll be at the stop light. Oh, let's check, Slack. Oh, is someone needing something? I need to approve something. I'm at my kids thing, like, you know, I'm involved, but, oh, great, they're in the locker room. Great. I'll check, you know, I just want to make sure that I'm, yeah, I'm always available, and for my team, as well as for, you know, the people in the workforce. I think I saw her doing that, just taking great care one, because she wanted, had such a drive to be successful. She was taking care of us. She wanted to be successful. People continued to invest in her, and that really ignited her to continue moving forward. And then just seeing her be able to go from, you know, HR manager all the way up to a chro level role in really kind of a short amount of time, if you think about it, and to when she learned HR for the first time and then was able to progress without that formal education or business knowledge.
Chris Rainey 7:56
Yeah, did you? Did you take away some lessons in terms of like you meant, you mentioned, did you just mentioned you have kids, right? Did you Yes, in terms of, like, how you balance that? A big challenge of people, of the guests I speak to is, how do you balance the the workload, the family and everything else is not always easy, right? It's
Casey Bailey 8:12
not, and I think specifically today, you know, she was working in companies early on that were just based in our little small town, or, you know, 30 miles away from our small town, up until she was at at&t, where she really worked, out of Seattle, Washington, all during the week, and my grandmother was there, and just seeing both the trade offs that she made for us, for her career, but also for us, and what her career was able to bring to us financially, right? And the opportunities that we had and and going to college or going on to law school, even though, just saying that one year, just really believing in ourselves and the things that we could do. And I think I try to do that with my kids, but working now, you know, at deal, we've got people sitting across 110 countries. It's an always on. I'm always saying this is like a game of football. Could be American or offend anyone. Any kind of football is fine, but it's like an ongoing game of football, right? Like 24/7 365, you've got customers on the field, team members on the field. People are coming on and off, taking water breaks, going to the locker room, something is always happening, and you're really having to trust people to come on and off. And I think when everybody works in that way, there's a lot of trust, empathy, respect for the time zones and for how people work. I think, obviously that's changed a lot since the pandemic as well, and more people going remote, but I think, I think that's that's really helped me balance my family. I'm balancing my family better than I've ever balanced my family, I guess I would say in my career, yeah, because of this opportunity to work the way that we're able to work now, which, which looked different for me. You know, 10 years ago, 12 years ago, when I had to go into an office. But. All day there, commute and trying to balance your family then is, is quite different. And my kids were young, so yeah,
Chris Rainey 10:05
and I think at this point it's more of like a more of a blend. Yes, I don't think you can really balance. It has to be, it has to be exactly integrated and blended together, right? This sort of notion of one or the other and this balancing act, it doesn't really play out too well. I've learned the hard way that I have to set up systems processes, you know, I've got a young, six year old daughter, and I have to be super intentional about how I'm setting, you know, spending my time and creating boundaries. And because I will work, I'll just continue. Otherwise, I'll just work, and I won't take the time off, and I won't all the things I preach to my employees I won't do a minute. You said it's important take time off. When was the last time you took time off? Like, today? I was like, nope. Today's the Christmas play, and we're very busy, but I am gonna go watch Robin on a Christmas play. And I like, will not, not miss, not miss that for the world. You know those moments you can't get back, right? Do you find that you have, like, a new found sense of appreciation for the work that your mom does, did continues to do now that you're sitting in the seat that didn't when you Yes,
Casey Bailey 11:10
yes, absolutely. I mean, I think she did a good job of exposing us. She gave us she would have me do translations of handbooks, or work on handbooks, or help her with an investigation or, I mean, we were in it specifically during our summer. She kept us, I love it busy and engaged. She's like, Oh, you know, you don't need to go work at Sonic or whatever restaurant I've got work for you here. And we would go to her office, and we would be exposed to that. We would go to dinners, yeah. I mean, we were, she was building our professionalism. I see that now, and I'm very grateful to her for that. But I think she was also, you know, building our business acumen as well. It's one thing to understand HR, but to understand business and be able to talk about the business is so critical, right? And building a people strategy, specifically now and specifically in some of the companies I've chosen to work for. So I'm, I'm very thankful for that
Chris Rainey 12:07
amazing and as that was not planned to all everyone listening of what our questions, but I was like, I have to, this is such a unique opportunity. I have to ask you those questions. And it's incredible that the way that that's shaped you, you and your sister, and the impact that you both now have on, you know, 1000s of people's lives that you serve as well. That's super cool.
Casey Bailey 12:29
It's sweet. Someday she'll just send us a text message saying she's
Chris Rainey 12:33
proud of us. So, oh, you send her this episode. I'm gonna, I will you guys. Sentence, what's her name? Her name is Karen. Karen Houston, shout out to Karen. So you mentioned so deals grown to 44 and a half 1000 plus now.
Casey Bailey 12:49
Yeah, we're, we were just looking at some of this data today. We're about 48 a little over 4800 people in 110 countries.
Chris Rainey 12:55
Wow. One of the big questions, and it's an ongoing challenge, is with with such a rapidly scaling, scaling workforce, how do you manage, sort of the that culturally, but also respecting the local nuance?
Casey Bailey 13:11
Because, yes, it's highly complex, right? I'm I tell people, wow, you know, if I wasn't working here and able to leverage all of the knowledge base, all of the individuals that we have working to create the compliant knowledge base for our customers who are trying to do the same thing. This would be a very hard and a very expensive thing to do, to really, truly be opening, open to hiring anyone anywhere, and although more of our roles now are like, specific to a region, or maybe we need someone a specific country, but still, we have a lot of flexibility in truly hiring anyone anywhere, and to do that compliantly. Just think about the cost of that. We would bring
Chris Rainey 13:58
that down for people, by the way, that don't know. Break that down. Yeah, so for like, you just said that, but most people really don't understand the implications.
Casey Bailey 14:06
So if you're you know, we are a US based company, and we could just be operating in the US, but instead, we've chosen to operate literally anywhere, but even if you're going to be in five other countries, right, where you're going to have people engaged with you as a contractor or as an employee, you've got to understand deeply and have the confidence right to administer compliantly against that country's regulations and laws, and in order to do that. So let's think about this. If I was, you know, I'm in 4800 people, I'm definitely in the enterprise category of a large company, if I was sitting somewhere else, maybe I've got work day as my core to my HR technology stack, as my HRIS. Maybe I've got greenhouse sitting on top of that as my applicant tracking system, and then I've got maybe a plethora of other systems that are sitting underneath workday, like a culture amp for. And, you know, performance and engagement or other things as I think though about it's not just those. Those tools aren't coming with compliance built in. They're not coming with policies or the right employment agreements that I need to use for the Netherlands versus Spain. They're not telling me that in France, I've got to pay x coefficient $50,000 for this role, instead of $48,000 to be meet the minimum requirement for pay. It's not telling me the pay parity rules in Brazil. It's not tell it. I have to go find that, right?
Chris Rainey 15:31
I gotta go buy How did you do that in the past versus now? Like just you
Casey Bailey 15:35
go buy it, right? You have to go find the resources, either through a consulting partner right legal fight, or you can hack together your own legal finance, tax compensation. You got to go get those consultants to build that database for you, but one of the and that can work, but you've got to keep maintaining that database, because if I go pay a million dollars to get five countries worth of information. I bring it in, have my people build it into work day, build it into all of our policies, create the new handbook, but then it could be static right away, right? Because, unfortunately, every country in the world is not on the same schedule for changing things. So then you've got to keep up. You've got to have a way of what cadence then are we going to look at this? What's our risk tolerance? Can we go a month without making sure it's correct? Three months, six months, 12 months, what are we willing to do? So that's, I think that's the burden that we're up against today, and specifically with, you know, we've got a new administration coming in in the US. We're a US based company. We've got to react to that. If you're sitting in Australia, do you have new works councils or things coming in depending upon where you're sitting. You're dealing with different things at different times of the year based upon election cycles. I mean, it's, it's just immense
Chris Rainey 16:49
things to keep up to date with.
Casey Bailey 16:52
I mean, it's fascinating, right? I think I've definitely learned. I thought I had learned the most in my career working well, one for my mom, and then two at Uber but now deal is is up it's up here. And just the complexity that we're dealing with every day we get something new that's like, wow, okay, hadn't thought about that. Let's, let's go find out that answer, and let's see how, how we want to deal with it here. But yeah, that the complexity that comes with operating in just more than one country, even can be astounding, but certainly 110 is next level. How
Chris Rainey 17:27
does it feel now, being in a role that? One, you're obviously doing this for customers. But two, you have, you have, you know, the tool internally to be able to access, utilize this, you know, yeah,
Casey Bailey 17:39
we're product managers. Me and my direct reports are in the product working with product managers, giving feedback. Our motto is kind of like, if it works for us, we're our most complex customer in terms of number of countries that we're in,
Chris Rainey 17:56
living and breathing.
Casey Bailey 18:01
Living breathing, building, iterating, start again. Yes. So if it works for us and our level of complexity, it will work for any company, like, how
Chris Rainey 18:11
many more countries should we get into this year? Yes, exactly, exactly. Let's just keep going. By the way, I mentioned to you before we went live, that we've just started, I am now ideal customer. And we have, I think we got seven employees in deals that are working in other parts of the world, and it was so easy. Like, I'm not just saying that as like to sell it, but like, it generally, like Shane and he and my co founder, that he's really picky, and he was, like, super easy to set up. Like, I think he did it, like, literally in a couple of hours. And then all of our employees got an email and, like, we just added a few things. It was, like, it was almost too simple, too simple to do it. Because we really focus on that, yeah. Because when you think about payroll and the compliance and the legal, you think, Oh, this is going to be an absolute headache. And as a small business owner, you know that was like, Oh, okay. And, and
Casey Bailey 19:04
then you have the confidence, right, that your people are seeing what they're supposed to be seeing and how they're supposed to be saying. Also,
Chris Rainey 19:10
me and Shane said we should have done this a long time ago, because we had it all over the place. I shouldn't be saying that, but we added, like, Excel spreadsheets. We're like, Okay, this is one source of truth. It's really simple as well. So yeah, and people could start using it for free, yes, so that I'm putting it out, I thought I'm standing for you now at this point, but I didn't know that. So Shane was like, we can use it for free to do X, Y and Z, and then when we start doing payroll, that's when we start paying, right? So that, so you that was just didn't know that. So yeah, as well. Yeah, super interesting. So I want to delve into the question a little bit more, though. Like, you know, culturally, how do you maintain the deal culture values when you're so distributed?
Casey Bailey 19:54
Yes, this is the number one thing I get asked by anyone, anywhere that I speak to about deal. How fully remote and distributed that we are across the globe. We really focus on this intentionally in hiring. Now, I joined in December of 21 so I just completed three years here. But in 21 the team had gone from 50 to 550 people between September and December of that year. So massive hiring, and zero to 50 million in ARR all in that back half of the year, right? So, tremendous growth. I come on in December, we're on spreadsheets. Yep, some people are getting paid in deals. It was everything, right? Every everything, everywhere to bring into consolidation and really focus on that single source of truth in our HR administration, but also in the people. We were like, hey, whoa. We've hired 550 people. And just really, our C level leaders have been hiring in silos, no aligned values or vision statements, no aligned compensation. Nothing is aligned. Let's figure out who we've got here. How did you go about this? What was important to you in hiring? Let's start working on some of our values statements so that we can begin to build hiring for those understanding what it's looking like. We were only in like 30 countries. 3035, countries, I say only at that time that we had people sitting across which seems like nothing today for us, and figuring out, okay, what's important, what are the attributes of these people, and then quickly seeing who was going to work out right as we moved into the next year, so that we could, we had to start building talent acquisition, because we went 550, to 1300 the next year, or 1500 a lot in that next year, so we had a lot of hiring, and we did want to make sure that we were hiring for deal. I think we've come an incredibly long way from 2021 and being able to explain what it's like to work here, talking about that ongoing game of football, talking about the self, direction, the autonomy, the comfort in working remotely. What it actually is to work remotely slack is our office. We have so many things that we talk to people about all throughout the hiring process to try to get in front of. So I think it's success when people opt out at that point, like I think I really need to go into the office two days a week, or I might not ever see my manager in person. I don't know if I'm comfortable with that or
Chris Rainey 22:25
but it's okay to be okay with that, though, right? That's the thing that you're like, not people avoid that part that it's not going to be for everyone, right? And it's okay to address that as a company and say, we appreciate that this is not going to be for everyone. Exactly that type of company and culture we're going to be
Casey Bailey 22:42
you have to be intentional, just be honest and true to what it is to work at your company, and then find all the ways to express that and find out if people really behaviorally can deal with it, is my recommendation. But what did
Chris Rainey 22:57
that look like from a practical point of view? Did you create like guide, like guidebooks, so you have, yes, map, everything you know like this is what like, because when you have that, you have to have a very well documented processes for everything, right? Yeah, what did that look like? And I'm
Casey Bailey 23:13
very OCD anyway, so yes. So we created our first hiring for our values playbook, hiring for our workplace playbook. And then we've come a long way in hiring, like those intake panels. What is the job? How are we hiring for the job? Because when I first started, it was like, hire a payroll manager. Okay, well, is this person? Junior payroll manager, senior payroll manager, manager. Like, what is this job? Because we had a lot of work on just what the jobs were. But hiring for our culture, it meant people really understanding what deal does. And that's actually, I think, I mean, it could bring you to tears, reading our engagement surveys, people talking about their connection to our mission and vision. Wow, I get to sit in Bulgaria and work for this US based company that is helping other people like me, sitting all around the world work for the best companies that they want to work for. This is incredible, right? And so people like are so tied when you can't buy that stuff, right? Like, people are so tied to that mission which makes them work harder, makes them more engaged in work, makes them try makes them care, just like my mom was telling me right back in the day. Alex is now the work that we do is about those our customers, right, like the companies that are our customers, but it's about the person, the human at the other end. And people here take that very seriously across every element, and we talk about that a lot culturally, it's driven through our objectives and key results, all of our OKRs goals are tied around that delivery for the human and again, that's really resonated. Yeah,
Chris Rainey 24:49
you know, I mentioned one of the use cases for the platform. We, our entire development team, are in Nigeria, and I would never have considered i. Hiring a team in Nigeria if I didn't have a tool like deal, to be able to do that as well. Like, we were looking everywhere. I mean, we're looking at the normal places that everyone looked like, where UK and other countries which were easier to open up entities in. And we were like, wow. Like, this opens up the entire world to us and to be able to do that as well. So I want to switch gears a little bit. One of the other challenges on this topic, which always comes up is, how do you then make sure that you compensate people, yes, fairly? Because we, there's a lot of, you know, you've seen a lot of LinkedIn posts about this topic of, okay, you're now going to outsource your team to this country to pay them this much and, you know, it's a whole mess, and many companies are still, to this day, really struggling with I love to understand your approach.
Casey Bailey 25:48
Yeah, so we take a pretty hyper localized approach to compensation. Compensation. I mean, there's 100 ways you could do compensation. I don't think that there's a right or wrong way. I think it's just how do you want to spend the money that you have available, and what's important culturally and from a values perspective. So actually, on compensation, when I first started, I spent a ton of time with Alex, our CEO, and with Philippe our CFO, to understand the budget, what do we have to spend so that we can determine what do we want to go build right? And that's has really stemmed from Alex, because Alex is a US company founder, but Alex is not a US citizen. Doesn't live in the US right. Has a very different perspective, honestly, to me, and my experience sitting in France and across Tel Aviv, and, you know, really challenged me to understand the global market more deeply than just, here's what US would pay. Oh, let's discount that by x percent, yes, for these other countries. He's like, that's not gonna be what we do, right? Like, let's, I wanna go. Figure out, go deep. What's cost of labor, what's cost of living, what's inflation, what's impacting people on the ground? You know, how can people, how do people live in these countries? Yep, there's always going to be people that are going to come in and just pay a US wage to everyone. Well, we need to be profitable, so that's not going to be awesome, but let's understand what makes sense compensation wise. And when we first started out, we had pay ranges. So at that time, we probably only had about 600 job profiles, and we had pay ranges for 30 countries. Like every job had its own local pay range. Okay? Well, as soon as we hit 50 countries, that wasn't scalable. So we needed to understand how then do we go about from a total compensation perspective, cash equity benefits understanding, how can we tier these countries into similarly situated countries and then operate? What's now, what over 4000 job profiles in just four country tiers. So four pay ranges every job. So, yes, so they're like regions, yes, essentially, wow, yes, interesting. And you know, you have to, like always, tell, remind people, like people believe that deal is a very US centric, us focused company, because we are US based. But we only have about 450 people in the US, the rest of our workforce, it's across the world. We have a little over a third of our population sits across EMEA, and then second is EAP, and then the Americas. So we're very much built. We very much built like a what I think is more of a true global compensation program, where we go seek out the country level details, rather than taking those percentages off of us. So that's been very core to who we are as a company, as a culture, philosophically values perspective, and we do a lot of work to educate people. Your workforce right? Can always agree or disagree with how you do compensation, right? You can any engagement survey will tell you you could always be doing it better, but we spend a lot of time educating people around how we do compensation and why that's important to us, and then that flows over into our product too, and some of the things that we've done from compensation reports and what we're seeing from our customers as well,
Chris Rainey 29:16
I was gonna ask you that, is that something? Maybe I should know that come our customer now, but, well, you knew that's something you help customers with. Yes, yep, yeah,
Casey Bailey 29:27
it's a number you could do. There's a lot of salary insights and salary calculators and things that you can look across the platform. We also put out an annual, basically like compensation report. It just came out maybe two months ago, as what we were seeing is some of the trends and where, you know, engineer salaries are on the rise in places like Nigeria and places across South Africa. Really interesting details for for folks looking at cost, but also looking at where various talent pools sit, and how to access those talent pools. One
Chris Rainey 29:57
of the things that came up while you was the. Sharing that was you're doing this at scale globally. How do you ensure you have a good onboarding experience?
Casey Bailey 30:10
Yes, I mean, we are, well, we'll have hired what it was it yesterday, 2028, 81. 2881 people this year, because how many people we've hired, and
Chris Rainey 30:24
so you need doubled yes this year alone. Yes, wow. Set to put in a context for
Casey Bailey 30:31
a second. We do have a 20% attrition rate sitting in there too. So some of those are backfills against our original headcount. Still okay, and we closed 6m and A deals this year, which increased the head count as well. So but yeah, we've hired net new having to onboard right 2800 people, and we have tremendous learnings across onboarding. We used to be just very focused on that, really just day one experience, because we had just so much downward pressure, just how many people we were hiring every year to date, just focusing on day one, day one. And since we've built out a people success team focused on, okay, let's sit back and map what's happening pre day one. Because, like in many European countries, you could be waiting three months for that person to start. So from the time that they've accepted an offer to this time that they're their notice periods, right? Yeah. So, you know, in the US, you don't have that two weeks, two weeks onboard someone, yeah, but we wanted to make sure that, because we're doing so much hiring again, a third of our population sitting there. How do we make sure we're like, they just don't get the offer, and then they hear nothing from us right until day one. So it looks different by country, even by individual, based upon that time that we're waiting to actually onboard them. So we've done a lot more work over the last 12 to 18 months around keeping people engaged, whether that be videos or messages from our C suite, or things about the product, or things about their specific team note from their managers, really keeping that engagement to make sure they start day one and have a great experience, and then we are still hyper focused on that day one experience, but also really kind of the first you know, it sounds traditional, but that first 90 days, we're in hyper growth, Right? We've added so much. Arr, so much. Head count. Things are constantly changing. 6m and A deals this year, like, if you just track someone's first year here and what's happening to them in those moments that matter. That's what we've tried to back up and say. What are the key things that are happening in that that first three months, let's say, and how do we make sure that we're also enabling the manager to help make sure that the person is onboarding and wrapping based upon what their job is. And how can we serve things up in self service and automated but also, and using AI, some of our AI tools on knowledge, but also, how do we make sure that they're feeling good about their role and then checking in on them? So it's come a long way, but again, I would just say the theme is just being intentional with it, and we still have a lot to learn. Look
Chris Rainey 33:04
looking back, you just mentioned one already, which is you realize we need to communicate more often in that time period. What are several other areas that you look back and say, Hey, we could do we could have done this better, and you are doing it better now, some mistakes that others listening can avoid. Yeah, I think
Casey Bailey 33:21
it's just organization, honestly, like being the business that we're in, there's a lot of not sexy things that we have to have people do around compliance, right? And compliance training or these things. Well, it was really messy and organized. It was coming in at the wrong times. It's actually a really great time to catch people when they're first onboarding to do those types of things, they kind of just have the space, right? Yeah, to get those things, those housekeeping items. So like, what are our housekeeping items that, like must happen, that no one loves, get those done. Give people the space. Tell the managers this person has got the space to do these things in this time period. I think those have really helped with one just getting those compliance things done, but then also making sure they can get that out of the way, and really thinking about in a regimented way what's happening in those first few days, first few weeks, at a more granular level. And I think that's helped the managers, too, because the managers were like, well, what are you doing versus what are we? You know, what's HR doing?
Chris Rainey 34:21
It's HR, no, it's your job.
Casey Bailey 34:25
You're a manager, yeah, this is what you're gonna do. You know? We, we like every, every company like us, right? We've invested a lot internally with promoting people into management. We also just have a lot of first time managers, yeah. And so we, we built a whole new guide program this last 12 months just focused on managing it deal. Because even if you've been a manager somewhere else, managing here is a next level, because you could have people, on average, our managers have people sitting across at least three countries, yeah. So just that alone,
Chris Rainey 34:55
one, one is hard for like, you know, right? So free. That's a whole nother complexity. It's different.
Casey Bailey 35:02
Yeah, so we want to onboard, and we've done a lot more in onboarding our managers specifically into the environment as well. So that's something I wish we had done a little bit earlier, especially
Chris Rainey 35:14
in the environment that you've built and the way of working you, it's even more important that you map out that entire journey and the moments the matter. And then you can kind of look at that as a team and say, Where are the moments that the human steps into the loop, where? And you can kind of like, map out all your comms all the way along the journey, right? Do that, and then you can map out all of the tech along the way, and then you and then the human, and you're like, Okay, we can see these are the moments about this. Is it? And, you know, like, and there's this, there's, there's technology out there that actually helps you do that. Now, I can't remember name a company on top of my head. It's really bad. I saw one recently that literally just does that. And it's so it's a game changer to be able to do that right, because trying to, trying to, it's hard enough to doubt when you're in an office to get together, you then do that globally, exactly. It's tough, so it's really important. And there's loads of research to show that that first 90 days in terms of whether someone's gonna you're gonna retain that individual, or they're gonna leave, is like the most important time. So if you, if you don't spend the time and energy up front it's gonna cost you? Yes.
Casey Bailey 36:23
I mean, we can already see in mapping our first year leavers, they leave in that first 90 days, if they're leaving exactly
Chris Rainey 36:29
as well. How do you ensure during the interview process, or you know, that even, maybe even before the interview, that you communicate that this is what it means to work here, so you don't get someone that comes in expecting something that, oh, okay, this is really not for me. This whole remote thing is that, do you have a specific question that, like managers ask? Everyone's
Casey Bailey 36:54
asking it, everyone on the panel is asking it in a different way?
Chris Rainey 36:58
Give us some examples. Yeah, so even
Casey Bailey 37:03
starting with the screen, we're going to be asking someone questions like, you know, tell us how you work today. Just starting super high end of the funnel, right as we start funneling, and tell us about how you work today. And if they're depending upon what their their answers are there. Oh, well, I'm working, you know, I'm at Amazon, and I've been called back into the office. Oh, well, you know, how do you feel about that? How do you feel like you best work? And you just kind of start digging in like you're an investigator on the police force, right? Like, okay, like, really wanting to get into them, telling you without any bias coming from our side. How do you like to work and in what environment do you work best? Because usually that is the most honest answer, right that they're going to give. Because when you start talking about when they when they move to the hiring manager, and the hiring manager starts talking about how we work here, Slack is our office. You know, using the technology, being comfortable with, you know, you could you are like, for me, for example, I'm in Utah, in the US, second worst time zone for deal, I believe, because,
Chris Rainey 38:10
like, a competition internally of who has the worst time zone, I can already see it, like, who has the hardest time zone? I do. I have these continents
Casey Bailey 38:19
because, you know, it's but it's real, like, I'm gonna wake up to 40 WhatsApps and 130 slack. That's just what it is, right? Because Europe is and then some of them are, like, waiting on Casey to wake up. Casey, are you up? What time is it there? It's 6am for her, she should be up. You know, it's like a whole funny thing
Chris Rainey 38:35
on that point, like, how do you create the boundaries that you don't cause burnout? And this is always on because, especially I've seen that happen, even to me personally, because we've got a lot of us clients, and they're like, I just kind of just was working non stop, day and night, day and night. And I was like, I just can't do this.
Casey Bailey 38:53
I guess this is where that how you control your day. We were actually just doing this with a company that we we acquired. They're based in South Africa, predominantly their workforce. I mean, 95% of their workforce is in South Africa. And they are like, Oh, how do we work here? We've got to work our whole work day, and then we've got to wait, you know, to work with these people at deal. It's like, okay, well, let's think about what you need to do, right? You're predominantly software engineers or people building our SaaS technology and payroll. You have a lot of flexibility. Like, do you need to work your work day, like a nine to five? Or, how do we think about your day and how you need to spend it? If you and who do you need to work with, and who do you need to interact with what's async? Are you not comfortable with async? So you're there's a lot of like, root cause things that we go through and to understand, like how based on role. But we've seen this most with the M and A work is, how do we think about reimagining that work day for you, because for myself and I give a lot of examples specifically as we're on. Hurting other executives, you know, that's their first question. Like, whoa, you know, I'm based in Austin, Texas, and like, the rest of the team sits in, you know, in Europe, how's that gonna work? Or I have a two team members saying, EAP, I'm doing it's like, you really have to, yeah, you have to take control of your day.
Chris Rainey 40:18
When they're in a meeting. It's like, well, we just gotta work around it, right? Like, exactly, like
Casey Bailey 40:23
you have to be, everyone here has to be very comfortable with async, first of all, and again, and have a high level of trust. So Alex is kidding, right? Like, oh, waiting for Casey, waiting for Casey, yep, sometimes they do need to wait for me, but they're also trusting. Like, she's gonna wake up and she's gonna take it right, and she's going to take it as far as she can on her time zone, or how she's running her day. I don't think any of my days look the same. I mean, I'm trading off with my husband on who's taking the kids to school or to the bus stop that morning. Oh, somebody's got a doctor's appointment. Oh, school got out at noon this day. Oh, and then the afternoon. I mean, everybody's in a different sport, and so that, you know, you got to divide and conquer, but so my day never looks the same. I mean, I might start early one day to reach a pack or late. I mean, just, you kind of just have to look at every day as a new day. That's my motto. I had my team made notebooks that say every day is a new day. And you just got to kind of take it for that, but be comfortable with that. And people who need, like, a more regimented, like, I need to work nine to five. It's not going to be the best place. We have some roles. We have some roles that that could work for. But
Chris Rainey 41:30
also, you're not measuring, like, the nine to five was invented during the Industrial Revolution, right? Yeah. And we're no longer not man, as I said, it all time. We're not we're not measuring time. We're measuring the results and the impact, right,
Casey Bailey 41:44
right? We don't care, as a company, when or how you get it done. Yeah,
Chris Rainey 41:49
you know, I mean, we trust you, just because you're here, all that you could be in your office all day and do nothing like, like, quite literally, right? And as an entrepreneur, I'm working the way you're describing anyway, because that's just the nature of being an entrepreneur, and it that took some getting used to, if I'm being honest, of not having, like, a time as well. The other challenge, I know, I know we're like, already way over time, but I'm just really enjoying the conversation with you, is like, how do you measure what good looks like in terms of results and and then hold people accountable without, without being the overseer of like, are you logged online? We can see you've not typed a keyboard.
Casey Bailey 42:30
How do you do but that's interesting, though, because we do. People can get lost in this environment, right? If you let them, if you're not intentional, if the manager is not intentional. People across three countries, three time zones, people could get lost. And so we, we really focus on on two things. One, I call it total engagement. It's really like a lot of inputs from making sure, like, if someone hasn't logged on to Slack or let their man and like none of our systems show that they're out, we should check on this person right, like making sure that we're equipping the manager and enabling them with data and insights across the people space on engagement, everything from our actual engagement surveys to use utilization of tools to making sure people are taking time off or Utilizing
Chris Rainey 43:20
if you can see that person is always online, you're like, hey, that's also a problem. Yes,
Casey Bailey 43:26
yes. So we really, we focus on that perspective again, and supporting and surfacing things to managers to enable them in their management of the teams in this environment. But then also from a driving high performance. Gosh, we've been on a roller coaster here and trying to figure out what, how are we going to do, OKRs, our objectives and key results. Are we KPIs, are we OKRs? Are we goals? What's happening? We've had a lot of iterations of these Since 21 and really, this year is the first year that I feel like, OK. This is feeling the best that it's felt we got on a cadence, a quarterly cadence, of business and individual planning, if you will. So every quarter, we revisit what's happened with the OKRs, our objectives from the prior, what was our attainment. But also we're looking at the individual, so business and individual every quarter as a wrap to see what's happened. What's going on? Did things get reset? How did you do we have a continuous feedback cycle that we've really built a strong muscle around in the past 18 months, but having those for sure quarterly check ins that are really things that everybody should have already talked about during the quarter. It's no new information. But yeah, this has really helped speed up our ability for people in ramp with all the onboarding that we're doing for people that were struggling or saw a dip in performance for some reason, where priorities changed, where M and A people have come in and changed the course, like product, road mapping, anything that's happening. We're a startup, so you know, we can't plan like annual we. But doing the quarterly this year has been, has been good. It's been our best. Can
Chris Rainey 45:04
you still call yourself a startup at this point?
Casey Bailey 45:08
I mean, I don't know. I still felt like when I was at Uber and we had 20,000
Chris Rainey 45:14
Yeah, we're a star, world's largest startup. Do you know, I speak to so many companies, they like start. I'm like, you know, you've got 80,000 employees. You can't, you can't keep telling me you're a star. I don't know what point that ends, just
Casey Bailey 45:27
curiosity like, what system do you use to measure, oh, we're using deal now, yeah, well, to measure the work. So we bought a company called zavi Earlier this spring, and we've rebuilt zavi into deal. It's our deal engage product. So we're testing this internally for ourselves.
Chris Rainey 45:47
I did not know about that gets fully launched. I don't think so. So much sense.
Casey Bailey 45:56
Again, it's you said it earlier, single source of truth. So we believe in the consolidation of the HR tech stack as much as we can, we still have an external vendor for applicant tracking, but everything else we're using, I love the fact
Chris Rainey 46:07
that you're building what your business requires, and that just so happens to also be your product. Like, that's like, hard to get your head around, where you think this is also how we make money, but it's also how we service ourselves, and we also succeed, because we keep reinvesting back into that loop that's super fascinating, like as a founder, to think about that full circle approach. Yeah, wow. I listen. I need to let you go. I was enjoying the conversation so much as well. I'm looking forward to that new product, because that'll be interesting. Because that's a challenge for us even now, we use, like, monday.com right now to mention, but I feel like there's room for improvement that can be made. But again, it doesn't talk to our other systems right in the same way. So we're still kind of like, you know, we've got like, integrations through Zapier and stuff like that. But, yeah, it can be. It's a bit of a headache sometimes. So before I let you go pie, piece of advice to other HR leaders now that are going to be embarking on this journey, or currently in the midst of it right now, where they've kind of got a distributed workforce, some in office, some remote What advice would you give to them that you wish you had when you started on this journey, and then we'll say goodbye, yeah,
Casey Bailey 47:25
yes, I think it's find your confidence. And by that, I mean find that right HR tech stack, find the right partners, find having the right conversations with your founder executive team. Just find the things that you need so that you have confidence and the delivery of what you need to do for your specific business. And I would say, don't listen to all the noise. There's so many trends and things happening right now, which I love hearing about, because I'm so curious, and I want to learn and see what everybody else is doing. But those are just things I'm adding to my toolbox, right as I come back and say, but what do we need to do here at deal? Where are we trying to do things different? What makes sense? Yeah, just, just find your confidence and then stick with it. Honestly,
Chris Rainey 48:13
I've really enjoyed this conversation. It's been so fun. And thank you for coming on the show, and it's really cool. We have to do next episode with get Karen involved. Yes,
Casey Bailey 48:23
Karen Brittany and Casey. Yeah, your part and advice
Chris Rainey 48:25
should have been to say, call Karen. We need to think Karen. Karen one 800 Yes. No, honestly, I love it. I would love to be around the dinner table with you, with the family. The holidays are about. Holidays. I can imagine your holiday conversations. I bet, I bet the rest of the family like, that's enough. No more HR. I can already hear your husbands right now be like, no more HR talk at the dinner table. All right, let's just enjoy ourselves during this time. But AI, I wish you were the best, great connect with you. I'll see you soon. All right. Thanks so much,
Casey Bailey 49:02
wonderful. Thank you.
Unknown Speaker 49:04
Ai.
More from the HR Leaders Podcast
Casey Bailey, Head of People at Deel.