IT Crafts HR – Kaylie Boogaerts from LaterPay

Maks talks to Kaylie Boogaerts, People & Culture Manager at LaterPay, about how to manage a team that is spread across 10+ different countries. Based on her experience in building a remote culture at LaterPay, Kaylie shares her insights on how to keep people aligned and connected and how to avoid getting them socially detached. She will also tell you what does she enjoy the most about working in a remote team, how important is the hiring process to make sure your future employees are ready for it, and how at LaterPay they use Slack to conduct recruitment challenges. Listen to a podcast and find out how the perfect cooperation between IT and HR department should look like.

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Maks Majer

Podcast Host

Maks Majer is a software engineer, co-founder, and CEO of ITCraftship, a company that helps both talented developers get a dream job at tech companies all over the world, and companies hire remote software developer superstars. He’s also a remote work advocate and helps startup businesses embrace the remote work culture. Maks is passionate about solving pains and removing obstacles by focusing on good software design and user experience practices. In his free time, he broadens his knowledge of business development as well as focuses on a healthy lifestyle that gives him the energy to get the most of a 24 hour day. You can catch him on LinkedIn.

Kaylie Boogaerts

People & Culture Manager at LaterPay

Kaylie Boogaerts is the People & Culture Manager of LaterPay. She heads the recruitment and culture efforts of LaterPay’s international team that’s distributed over 10+ countries. Thanks to her international experience (studying in Belgium and Japan, and working in Ireland, the UAE, and Germany), she highly values diversity and inclusion. Outside of work, you’ll most likely find her hanging upside down in an aerial yoga class, traveling or eating lots of good food. Follow her on LinkedIn.

Something that you wish you have known earlier

Transcript

Maks

Hello. Today, my special guest is Kaylie Boogaerts, who is the People and Culture Manager at LaterPay. Hello Kaylie, it’s great to have you here.

Kaylie

Hi, thank you. It’s nice to be here. Very excited.

Maks

Kaylie, can you please tell me something about yourself and describe the position and responsibilities that you have at LaterPay?

Kaylie

Sure. As you already introduced me, I am a People and Culture Manager at LaterPay. What does that mean? I do all things, people and culture or HR-related at the company. I’m the only people and culture person in the company. So I had recruiting, onboarding processes and efforts, giving feedback, HR admin, organizing the team retreats that we have 2 times a year, etc. 

I do this for a team of around 50 people. They are distributed over more than 10 different countries. And we have 2 offices, one in Munich, one in New York. But as I said before, the people are mostly distributed so we are a remote-first company.

Maks

Awesome. I actually wanted to dig in a little deeper on that. I’ve seen that LaterPay is a company that actively promotes remote work. You mentioned that your employees work from 10 countries. Could you tell me a little bit more about where these countries are? Which are the countries and cities where your employees work from? Is it common for a company and the team members to work across different time zones?

Kaylie

Yeah, definitely. We have a lot of people in Germany, in different cities in Germany, like Berlin, Munich, but also in smaller towns. And then we also have people in England, Scotland, Denmark, Belgium, Italy, France, Poland, Croatia, Canada, and in different states in the US. Then on top of that, we have a lot of people traveling and working at the same time. 

Maks

Okay

Kaylie

Right now we have somebody who’s been working from Japan for a couple of months. We had somebody who was traveling Southeast Asia for a few months as well. There’s definitely a lot of different time zones. We try to be as asynchronous as possible. We do notice that we need some synchronicity or some overlap from the team members and we ask that from them as well.

Maks

Okay, so I was actually going to ask you how is it working for you? You mentioned that you have some requirements for synchronicity. Could you tell me a little bit more about that? How do you make that work?

Kaylie

Yeah, sure. So the requirements kind of depend on the team. But in general, we asked for at least a 4-hour overlap with our European team. Which is depending on where the people are, the US people sometimes would have to get up a little bit earlier than like a 9 to 5 job. If people are working from Asia, they may have to work a little bit later into their evening so that they can have their team calls and half that overlap with the team.

Maks

That makes sense. You’re clear about that during the whole recruitment process and when onboarding people, you make it clear that you have some specific expectations, sources, synchronicity, and overlap, right?

Kaylie

Exactly. We make sure to put it in our job descriptions when we publish them. So that from the very start, it’s clear. We talk about it throughout our hiring process as well. If we are looking at somebody who’s working from California, for example, we make sure that they understand that we do require an overlap with our EU team – as most of our developers are in Europe. Then we talk to them about if that is possible for them because we don’t want them to join the company and then figure out that it is the lifestyle or a kind of like a schedule that doesn’t fit their lifestyle.

Maks

Okay, that sounds really great. Could you tell me as an HR professional, do you see any challenges that are typical for managing people in a remote company? What is like the biggest, most serious problem for you in that area?

Kaylie

Yeah, I think our biggest challenge would definitely be keeping people aligned and connected.

Maks

Can you tell me a little bit more about that? Like, what do you mean by keeping people aligned and connected? How do you deal with it?

Kaylie

Yeah, so what I mean by aligned is making sure that everybody is working towards the same goals, and making sure that people know what the company goals are. Then connected is like from the very kind of from a people perspective. As in like making sure that people don’t feel isolated from the rest of the team, if they are working from home, for example, and they don’t have people physically sitting around them. 

How we deal with these challenges is, first of all, we’re very clear about it during our hiring and our onboarding process. So we ask about what work environment they thrive in. And if they are quite independent people, or do they need a lot of hand-holding, and hiring and onboarding is the foundation of everything. 

Then another thing is, we are very heavy Slack users. Slack is basically a virtual office. So we use Slack both for work discussions, but also for non-work-related chatter, kind of. So people also use our Slack for talking about wellness, music, pets, kids, anything like that. Then, also for alignment, and connection actually. We have a weekly company video call where somebody from our management team is presenting something or giving updates, but also sometimes one of the team members might do an update on what they’re working on as well. 

We have our all hands. We have our team retreat where we try to get everybody physically together, again, for both alignment and connection. We are using OKR – Objective and Key Results to align the team as well. Then we try our very best to foster a culture of transparency, of inclusion, of psychological safety too.

Maks

I see that you’re very mature as a remote organization, which is, I think, very helpful for all the listeners out there. And you mentioned a little bit on the alignment. I think that kind of aligns with my next question about people who have doubts, that with remote work style, it’s hard to retain the company’s culture when you’re distributed.

You have already mentioned a few things that help you retain that culture and kind of align the whole team. Can you tell me a little bit more about what’s your view on this challenge? Dive in a little deeper on how do you build a remote culture at LaterPay?

Kaylie

Yeah, sure. I think, first and foremost, you have to figure out what your culture is, or what you want it to be, and how you will live it. So you wanna lead by example, you wanna talk about it, you wanna make sure that it’s very visible for your team. Because if you have your values set but you don’t live them, you don’t talk about them, the chances that it will actually translate to culture are quite, quite slim. 

Then we talk about them a lot. We try to make sure that if somebody is doing something that is against our values, that they’re aware of it as well. And we talk about how they can do the specific thing differently in the future to align with our values. I think LaterPay is the first company that I’ve worked for that’s distributed, and it’s also the company that has the most divided culture. So I think it’s not a matter of being remote, it’s more a matter of living your values and living your culture and leading by example.

Maks

Yeah. A lot about being mature, knowing what kind of values you want to promote, and making sure that the entire team knows about that, and lives that. I like that you mentioned that. I wanted to just follow up on this just a little bit more. 

I’ve seen a lot of companies that are very mature in the remote space, like for example, Gitlab. They have very well defined and described employee handbooks and documentation. How they work, how they communicate, what their values are, how they are represented. Do you have such a thing at LaterPay?

Kaylie

Right now our documentation is on Atlassian. We use Confluence is a wiki. One of our Confluence spaces is like an introduction to the company. And there we have our values and examples of how you can live those values. Basically, all this information that you need to know coming into the company, you’ll find on our wiki. 

When a person joins the company, I also always make sure to walk them through our values, our goals, so that from the start, they know exactly what we’re working on and what we’re working towards, and they are immediately as aligned as possible.

Maks

Yes, that’s really great. This is something that I’ve noticed a lot of companies that are on-site lack. The companies that have been working remotely for a long time, and who are mature within this work style, they really care about they are making sure that the onboarding process involves learning about the values, learning about the way the company works, then how to live those values. I see that at LaterPay you’re also at that stage which is really great. I also want to ask you from a personal perspective, what do you enjoy the most about working in a remote team?

Kaylie

Sure, I think the thing that I enjoy the most is the diversity. So there’s diversity and things like background, culture, language, education, age, opinions, experiences, and this diversity, it brings so much to the table. And for me, with our current remote team, it’s been very inspiring to work together with these people with all these different backgrounds. 

As they bring a lot of drive and a lot of support and understanding and compassion to you or to the company as well. So that’s been one of the main things. And then one other thing that I really, really enjoy about having while working at a remote company is that we have a lot of flexibility. Where we work from but also when we work. And I can lie, that’s pretty amazing.

Maks

Absolutely, I’ve been working remotely for quite a while myself. I see that being able to work when you are the most productive and organizing your day around work and around some personal stuff that you get to deal with. You can really make the work great for you and for the company that you work with. This is also something that I appreciate a lot in the remote work style.

Kaylie

Yeah, it’s the best.

Maks

Also, you mentioned a lot about the people and the time zones and how some people are working from many different places, and like maybe making the remote work for them so within the location and the flexibility in time, but also, considering the overlap, I wanted to ask you, do you have any good practices around? Like having people not getting socially detached. I have seen that it is a challenge for people who work remotely.

When they work mostly from home, after a few months or a year, they start feeling very lonely, mostly because people are social animals, and, you know, we like to interact with other people. Have you seen that happen to some of your employees that they were struggling after a time to get socially involved and how that affected their work life and personal life? Do you give any advice for employees on how to manage that?

Kaylie

Yeah, sure. We have seen it at our company. We had somebody who actually left the company, specifically because of this reason. They needed social contact, and they were really missing it. So I think part of it is really that you have to be a person who can do this whole remote working thing. And for some people, it just doesn’t work. 

I think that they miss a vibrant environment where they can have a chat with colleagues and go out for lunch together. And having had that experience with somebody who was a great team member, really, it’s something that we’ve been focusing on a lot. So once people join the team, we have quite a big onboarding process where we have a lot of check-ins. And it’s something that I always check for, to make sure how are they feeling. Are they feeling connected to the team, how is remote work working for them? Are they feeling lonely? Yes or no. 

And then to help with this if people are feeling lonely. We really encourage people to be active on our Slack, in our non-work related channels and connect with people that way, but also to really take care of their work-life balance. I think working remotely, or especially working from home, it gets easy to get sucked into your work or to not have a strict break, like ‘Okay, this was work, and now it’s time for my private lifestyle’. 

We try to be very encouraging on like you do your work. We trust that you’re doing your work, there’s a lot of trust and ownership, but when you signed off, please make sure that you sign off and you do whatever social things that you need or want to do. We don’t want people to kind of be stuck on their laptops and checking their phones all the time. We want people to switch off.

Maks

Yeah, it’s great that you’re keeping that in mind, and that you focus on helping your team to overcome these challenges. Because I’ve seen remote employees have trouble with that so many times. They wouldn’t really sign off after they finished their work. They would be constantly available on Slack, or constantly available on their email and they would never sign off, never switch off, and that didn’t really work well for the balance between their personal life and their work-life, and sometimes lead to burnout.

It’s really nice that you’re thinking about this in your company and about your employees’ personal lives and how that will affect it. I’ve seen people who are really struggling to be social and are feeling lonely, because of that they are going to a shared or co-working space, or just working from a cafe and making it a habit to occasionally visit places like that, kind of helps them with staying in touch with other people, and to just get a little bit of this kind of office environment where they can grab a coffee at a coworking space and just have a chit-chat with someone else there. Exchange experience. 

Also, that helps with the diversity and meeting other people and getting to know them, which is really cool. So this is something that I also recommend to people who start with their remote careers and haven’t really worked a lot. To be mindful of it. Not to just fully focused on working from home and saving time on the commute, and all of that. But also to think about their psychological health and just go out, and try to make it a habit.

Kaylie

Yeah. Try out different stuff. See what works for you. Exactly. 

Maks

Yeah, that’s right. So being a software developer, and IT recruiter myself, I have to ask you about hiring and managing remote software engineers. Do you think it is different in any way from other remote positions?

Kaylie

I think it’s mostly the same. It’s not that different for us, especially, because our hiring process and interviewing process focus on our values and our culture. Focuses a lot of ownership on being independent, while also making sure that you’re collaborating with your people, with your team members around transparent communication. I think the focus is quite similar. I think one thing that will be different for our remote engineers versus other positions is that our engineers usually have more interviews that are written on Slack because they are heavy Slack users.

Maks

So you actually have recruitment challenges that involve communicating on Slack with other team members on your team?

Kaylie

Yeah, for sure. We have a very structured interviewing process. That helps us with finding the right person and for our engineers that includes looking at the interview stages. The first interview is written on Slack with one of our team members. Where we look at what is their motivation to some basic fact-finding, look at how their written communication is, of course, because the communication with our engineers is on Slack, written. 

Then the next interview stage is a tech interview, which is a video chat instead of a written Slack interview, where they do pair programming. We focus on tech skills, of course, but again, also on communication around the whole pair programming. And then the next interview is again, on Slack. Again, a written chat, basically, where we look at their self-awareness, their independence, what environment do they thrive in, that kind of stuff. 

Then the next interview is, again, a video chat, where we give them time to ask all of the questions that they have left for us. We’ll ask a few more questions around culture and leadership. So 2 out of 4 interviews for engineers are on Slack.

Maks

I see that it’s changed a little bit from the recruitment process that I’ve written in the past where you have been interviewed by a media lab buyer. You’ve added a little bit more, especially on the site of Slack communication, and on the first tech interview introduced pair programming. 

I’m not sure if this is your area of expertise, but it would be very interesting from my perspective, as an engineer, on like the tech and pair programming skills. What kind of challenges and what kind of skills are you looking for at that stage? What kind of challenges do you focus on? Are they more algorithmic? Are they more like close to the technology that you’re using, and like practical use of the frameworks and libraries? I’m not sure if you know anything about that.

Kaylie

Yeah, so I don’t know all the specifics out of my head, but we try to make our tech exercises or pair programming as practical as possible. So we will try to see if there is a specific language or a specific framework that is required for the position. We will try to make sure that our exercise is with this framework or this language.

And what we focus on during these tech interviews is, again, like the communication around it. We want them to be talking as they’re going through this exercise and telling us about what’s going on. What are they thinking about? What are they leaving out, because it is like an exercise, and they only have a specific amount of time. We’re not expecting people to know everything.

Maks

Like from the top of their head.

Kaylie

From the top of their head, exactly. And they can go look stuff up, but they need to know where they are going to search it up, and what that they want to use within their code. Yeah, that’s what we focused on.

Maks

Awesome. I like it. It’s very practical. And this is the approach which we like to use in our processes too. I’m interested also, are using any specific tools to help you with the pair programming, or is it just like Google Hangouts, or Zoom? Or maybe any special tool for tech screening?

Kaylie

I think right now, we’re just using Zoom calls. And then we ask the person who is being interviewed to share their screen. I think it’s quite a simple setup, but it’s been working for us so far. 

Maks

Okay. I also heard opinions that the difficulty of recruiting new employees also comes from a lack of understanding between HR and other departments like tech, for example. Is that true in opinion? And how do you think the perfect cooperation between these different departments in the company should be to make your work the most effective as an HR expert?

Kaylie

Yeah. So here at LaterPay, I haven’t experienced that lack of understanding, or at least not yet, fingers crossed. But I think it’s also because I put a lot of focus on setting expectations right and being very transparent throughout the whole process. So I set very clear expectations from the start with the hiring manager, like, what are their responsibilities? What do I need them to do, and to take care of? What are my responsibilities? And also with the hiring team? Like once you have done your interview with the candidate, what do I expect from you? I need your evaluation uploaded in our recruitment tool. 

And we are a relatively small company, only 50 people. So we’re still very well connected. I know everybody in the company. And that makes it very easy to work closely with the hiring manager, to make sure there is that transparent communication. Also, not only between me and the hiring manager, but the entire team can basically follow what’s happening on Slack. We’re also constantly improving the process, the communication, thanks to suggestions that the team makes as well.

Maks

Okay, awesome. I’m glad to hear that you haven’t experienced that. And I think your experience will be very useful to others who actually have that kind of challenge. And my last question is, can you give some tips for HR departments or HR professionals from other companies that could help them improve their work. Do you have some tips like that or something that you wish you have known earlier?

Kaylie

Sure. What I wish I would have known earlier is definitely that you don’t have to do it all yourself. I personally am a perfectionist. I like to do everything perfectly from the start. But it’s impossible, you know, and you don’t have to do it that way. And you also don’t have to know it all. Because there is a team around you that is very supportive, that can help you with whatever you’re doing and make suggestions, give you feedback on everything.

For me, even though I’m the only person in our People and Culture department, we have a lot of people in our company who care a lot about people and culture, and who are always willing to make a little bit of time to share experiences, or to just talk things through or to brainstorm. So, yeah, it’s a learning curve. That’s okay. Keep your focus on people, and basically, you get back what you put in regarding respect, support, collaboration.

Maks

Awesome. Well, thanks a lot for sharing all of your experience, for providing tips that will definitely be helpful to a lot of HR people out there on the tech and non-tech space. But I also think that you shared a great deal of information that will be useful not only for people who are hiring remotely or working remotely, but also information that can be translated into other processes.

And maybe with that information people can learn that remote work is something that it’s worth considering, it’s worth trying, that maybe comes with some overhead, but at the same time, you get a lot of benefits out of it. So I want to thank you a lot for taking the time and speaking with me. Well, I hope that you’ll enjoy doing the great work at LaterPay with all the remote culture. I’m looking forward to connecting with you in the future.

Kaylie

Great. Well, thank you so much. It was a lot of fun.