Chili Piper Builds Remote-Work Culture And AI Skills Across 36 Countries

November 13, 2025 00:21:56
Chili Piper Builds Remote-Work Culture And AI Skills Across 36 Countries
The Josh Bersin Company
Chili Piper Builds Remote-Work Culture And AI Skills Across 36 Countries

Nov 13 2025 | 00:21:56

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Show Notes

Hallie Condon, Chief People Officer at Chili Piper explores how the company uses AI to optimize employee experience in a fully remote, global environment.

Hallie shares how Chili Piper empowers its workforce across 36 countries by intentionally building culture, leveraging automation, and fostering transparency through innovative decision-making processes. The conversation delves into the company’s unique approach to onboarding, offboarding, and continuous feedback, as well as their commitment to democratizing input and encouraging experimentation. Hallie also discusses Chili Piper’s focus on AI enablement, including launching an AI stipend and developing internal tools to streamline HR operations.

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Additional Information

Culture Always Wins (Video)

Gen AI Is Going Mainstream: Here’s What’s Coming Next

The Big Reset Playbook: Organizational Culture & Performance

Galileo: The World’s Trusted Agent for Everything HR

 

 

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Episode Transcript

[00:00:04] Speaker A: We don't talk enough in HR about just experimenting with new things that people haven't done. It always feels like we're trying to reinvent something that's already there. And it's like, well, if that, if nobody likes that, why don't we do something different? [00:00:21] Speaker B: Welcome to a new episode of the what Works podcast series. In this episode, Cathy and sits down with Hallie Condon, Chief People Officer at Chilli Piper, to discuss building a fully remote global culture and how Chili Piper empowers employees across 36 countries. They explore the company's approach to connection, automation and decision making, as well as how AI is being used to streamline HR and foster innovation. Let's get to it. [00:00:49] Speaker C: Hallie, welcome to the what Works podcast. [00:00:53] Speaker D: Thanks. [00:00:53] Speaker A: I'm happy to be here. [00:00:55] Speaker C: So excited for our conversation. So let's, let's jump right in. I know we have lots to cover, so tell us to get started. Tell us about yourself and a little bit about your company. [00:01:05] Speaker A: Yeah. So I'm Hallie Condon. I lead the people function at Chili Piper. We are a fully remote company operating with employees in 36 different countries. But Chili Piper is an AI powered platform that turns buyer interest into booked meetings. So we basically make it easy for potential customers to, to talk to your team the moment that they show interest. So whether that's through a forum or a live chat or a partner referral or maybe even an in person event, that's what Chili Piper does. So we have lots of engineers that work here, product managers, product design, and then of course we have our revenue Org, so account executives, account managers, sales development reps, and then of course customer support, customer success teams. [00:01:58] Speaker C: So yeah, got it, got it. So fascinating. So interesting that you have like this AI kind of powered product and I know everybody's talking about AI. Also explains why you probably have all of these different countries as well, where you have people and talent in those different countries as well. So how do you manage all of them from an HR perspective? How do you make sure that all of them, you have all of their information and all of that? How does that work? Because it's challenging, right? 36 countries for 140 people, that's, that's a lot. [00:02:31] Speaker A: Certainly I would not be able to do that by myself. So we utilize partners like Oyster HR as an example. So for all of our employees and contractors outside of the US we manage, I guess like the compliance portion of their employment through Oyster. Thank goodness for them because I don't know how else we would keep up with all of the employment laws, regulations and things like that. And I know for me as an HR person, that's not the type of stuff I love to spend my time doing. I want to spend my time on like the strategic work rather than like the policies and compliance. They really help me with that. And then on the US side, we work with justworks to manage sort of like that compliance and payroll piece. But then what connects everybody and like, I guess the system of connection and truth for our employees and their information is hibob. And hibob really helps us in terms of getting people onboarded, offboarded, sort of all those touch points in the employee lifecycle. Hi Bob. Really helps us and then also helps us kind of make those workflows customizable based on where those employees are located first. [00:03:53] Speaker C: On the hibarb thing, we also use hibarb for our own company as well. And for us it was really so appealing how easy it was to implement. So it took us, I think, a weekend to implement hibarb for us. How did that implementation go? How long did it take? Was it easy to do? [00:04:11] Speaker A: Interestingly enough, I actually have implemented hibob two times. [00:04:14] Speaker C: Oh, wow. [00:04:15] Speaker A: The company I was at prior to Chili Piper, I had actually just finished a self implementation of hibob there and it was very easy. I was very impressed with how smoothly it went there. I was. I had only had 30 employees that we were working with. We were much earlier stage startup. And then when I moved to Chili Piper, we had a different tool that I didn't, I didn't love. It's funny because I had demoed them, I wasn't impressed with the demo, but then I ended up having to use them at Chili Piper and I was like, oh, I want this, like, hi Bob. Automation. So we went through our decision memo process and ended up moving over to hibob. And even with the migration of data from one system to the other, the setup was very easy. And that's one of the things I also really like about the tool, is that the user experience and the user interface is very intuitive. Even if I don't know necessarily how to do something I can figure out in a couple clicks. The other thing that's nice about that too is with how flexible the platform is, you can sort of like create these different workflows that maybe aren't necessarily something out of the box that they recommend, but are something that you can kind of hack together. So to automate administrative work that you'd prefer not to spend your time on, that's Fantastic. [00:05:34] Speaker C: Can you give us some examples of these workflows that you have automated yourself and you're just using there because it makes it much easier. [00:05:42] Speaker A: Yeah. So an obvious workflow that's sort of an out of the box workflow they have is onboarding. So we certainly have an onboarding workflow set up. We utilize their task lists to automate timed emails that we have sent out to somebody as they're sort of in that pre boarding process. So, you know, the first email that you'll get from hibob is, congratulations, we're so glad you're joining. Here's all of the communications you could expect from us and roughly when you're going to get them. And that includes things as simple as when am I going to get the login for my email? So we built all of that into our task list and then we have different task reminders through the onboarding process to have people take part in different activities. Like something as simple as nominate one of your coworkers for this weekly award that we have. So it gets people familiar with other systems that we have, but then also get them more involved with connecting with others. Some that we've sort of hacked together. We have automated our employee verification requests. So oftentimes you get people that are like, I'm applying for a loan and I need verification of my employment. We have a flow in hibob where people can go in and request their own employment verification. They can let us know if they want their variable pay included or not included and then it'll give them that letter. And then the other thing that we have also set up a workflow for is offboarding. So somebody wants to put in their notice, they've likely probably let their manager know rather than them having to let me know. And then doing all this manual work, we have them trigger the workflow by submitting their notice and then it triggers the appropriate workflow, including the follow up communication that we would send normally after we would do sort of an exit interview. And we, we give people the option for their exit interview if they wanted to feedback form or if they want to talk to somebody live. We have some people that feel more comfortable giving feedback in writing rather than live. And so we want to cater to that. And that also saves us some time. Probably gets us better feedback too. [00:07:48] Speaker C: So do you use it for other things too? Hypop. I know hyperpad has many other capabilities too, in addition to the core HRS and HR information. [00:07:57] Speaker A: Yeah, so we also utilize their talent module and then we use their your Voice tool as well. So with the Talent module, we're mostly using their feedback and surveys. So we, we run a number of surveys every year. There's two surveys we run every year, no matter what. That's our Thrive survey, which is our version of the engagement. An engagement survey. And then we run a survey after our company trip every year just to, you know, get an understanding of how well people feel like they connected with one another and just get general feedback about the trip. What could be better, you know, what went well. But then throughout the year, we run different surveys based on certain initiatives that we're running. So as an example, one of the surveys that we're running this year, we've been doing a lot of training around helping people develop skills around empathy, but then like trust building and things like that. And so we've been running feedback surveys on how well that's working for people, how well they connect with the content, things like that. So that helps us kind of build additional data points that we oftentimes have to use in our decision memo process when we want to make large decisions. So helpful. [00:09:16] Speaker C: Tell us more about the decision memo process because that sounds very interesting and unique. [00:09:23] Speaker A: Yeah, we're very heavy on the async kind of way of working, especially with people in so many different time zones. But we also want to make sure that we're transparent. Right? We, we want to make decisions out in the open. And so one of the ways that we do that is through this decision memo process. Many decisions that are made at the company go through this process where essentially, let's use an example of when we migrated over to the hibob tool. So it wasn't just something where I could say, oh, I want to migrate over to hibob. We're just going to do that. I had to document what is the problem that we have, what would be the ideal vision, and then laying out all of the different options that I would have. So the first option is always do nothing. What are the resources involved in that? What are the pros and cons? And then, you know, looking at what the other options are. And then basically anybody can make a recommendation, make a comment, ask a question, and then generally the decision memo has an assigned consensus caller. So that's sort of like the decision maker based on all of this information and then we move forward with it. So. So yeah, it's a really, it's actually a really great process to like make sure that you are considering all possible options rather than just assuming that the thing you think is best. Is best. Yeah. [00:10:44] Speaker C: So it's fantastic. And so employees can weigh in. Is it posted on a website or how do you communicate those decision limbs? [00:10:53] Speaker A: We have a slack workflow. So basically people just put the link to their decision memo in this spreadsheet. It posts to this Slack channel so people can see what decision memos are currently active. And then when the decision memo closes, it also records what the ultimate decision was or what option was selected on the decision memo. So we, we have had decision memos too, where it's like, people don't necessarily agree with whatever the final outcome was. And so we'll have like, that time periods where it's like, okay, we're going to Review this in 6 months and see if, like, we still feel like we made the right decision. We used to have a contrarian club. So if you disagreed with the decision memo and then the decision memo came back up and your decision that you recommended was actually selected, again, you'd get like a bonus to encourage people to feel like they didn't have to just agree with, you know, if our CEO was commenting in the decision, they didn't feel that they had to agree. [00:12:00] Speaker C: Wow, that's fantastic. So people actually do not always say, oh, this is a great idea. But they do bring in alternatives, which is great. I think that's awesome. It's very empowering and very democratizing for people to feel they have a say in the company. [00:12:15] Speaker A: Yeah, yeah. And I think it also. The other kind of nice thing about it is you can go back and refer to it if somebody onboards. Like when I onboarded, I didn't understand why we selected the tool we did or what else we looked at. And so I was able to go back to the, like, original decision memo and look at, oh, why did we select this tool? What other options did we look at before deciding on it? [00:12:37] Speaker C: That's. That's really fantastic. I've never heard that. But this is. Seems like a. What a great way of not just communicating after the fact, but getting input before the fact. Because oftentimes the best decisions are informed by the front line. Right. They know sometimes more than we do. [00:12:54] Speaker D: Right. [00:12:55] Speaker C: So, wow, fantastic. So the things that you do on the surveys, for example, you ask them also maybe input on things that you're trying to decide in the decision members, for example, or how did that decision work for you? Or any of those kind of things. Are those what topics that you also cover in the service? [00:13:16] Speaker A: Yeah. So as an example, like when I first started, we originally had a development stipend that we offered for people. I think it was like $2,000 a year that people could use. It was sort of automatic. You would get it. You didn't really have to go through much of an approval process. When we went through our rrif, we also did some like cost cutting, and that was one of the things that we decided to sunset. Well, we got a lot of feedback in our surveys that people didn't feel like they had enough development resources. And so that was one of the things we actually used in the decision memo to say we should do the development stipend again. So that was something that we reactivated for people. And what's nice about it too is that we were able to see from taking that action the following Thrive survey. We had data to also show that we did this. This helped create this outcome or fill this need for people. That's a straightforward example. [00:14:09] Speaker C: Yeah, that's great because all of these examples make it real. So how the decision memos go with the surveys and vice versa. So it's kind of this ongoing circle of listening, getting input, feeding back the information, getting some more input, and then listening how it's going. So this ongoing kind of listening circle and engagement circle and democratization of also decisions, which is fantastic and sounds very empowering for people. So maybe, I know we covered a lot of ground maybe in the last few minutes, tell us where you're going next in kind of your whole hr&hrs and kind of HR systems journey. But then also what's next for you overall in kind of maybe more strategic things that you're doing with the organization. [00:15:00] Speaker A: Yeah, so I think this is maybe connected to both. So we're putting a big focus on AI right now. I mean, what company is it? Right. Creating different opportunities for people to learn, but in a way that's safe. So I'm sure this is also not unique to Chili Piper, but we have had a lot of fragmented and AI utilization. So we've got some teams that are like really utilizing it. We've. We have like a team of people that is sort of used as a resource to help other teams kind of like build different flows. But what we really want is like, we want everybody to feel comfortable using it themselves. And so one of the things I'm working, we've. We've just recently stood up like an AI enablement task force. So one of the things that we're doing is we're going to be launching an AI stipend for employees so that they can, they can use and experiment with tools on their own and then kind of share with the team. Was it a win or a fail? You know, if it's a win, you know, is this something that we can put together into a playbook for other people to utilize? Because I think that what we're sort of discovering is that AI adoption is fueled a lot by people's like, I guess, like people being able to utilize the tools themselves. And like, you learn a lot through doing and, and, you know, tinkering, I guess. And so, so we're trying to sort of enable employees to be able to do that and to feel, I guess, safe doing that and confident doing that. So that's one of the things that we're, we're doing. My team specifically, obviously, is we're trying to automate as much as the, as much of the administrative work as possible. I know Bob has a AI development that's going to be coming out. I, I'm not sure if it's this course quarter or next quarter, but yeah, I, I've seen their recent webinar on that. So that'll be something that we will hopefully be able to utilize. But we're also like, experimenting with things like building an HR chatbot so that, you know, every HR person, I think, would probably tell you that they get questions about, you know, policies or things like that, that it, you know, they've already. The information is out there. People just for whatever reason, can't find it or, you know, whatever. So, yeah, so one of the things that we're working on is just is building a simple HR chatbot where people can go and, you know, ask some of the common questions that we get to get the information they need. [00:17:59] Speaker C: That's always super helpful and I think reduces a lot of the questions that you get. But then it's also making easier for the employees and the managers in the company to find what they need to find. Because you're not working 24 7, I'm sure, and your team is. [00:18:16] Speaker A: I'm like, well, I think people would love me to be. I am. [00:18:19] Speaker C: And you shouldn't. You shouldn't. And the chatbot will be right. And also, I mean, we've seen studies and we've actually done a study ourselves where we saw, for example, this kind of chat feature. This like, conversational AI retrieval of information or pointing them in the right direction takes away 95% of the time. So if it took them five minutes to find the information, now it takes them 15 seconds. So that's a huge time saving and makes the experience a lot better too, right? They're going to be happier with that too, because if they can just ask it right there and then get the answer right away, a much, much better experience, for sure. [00:18:57] Speaker A: Absolutely. [00:18:58] Speaker C: And you are an AI company, right? So it goes probably without seeing that people expect. Probably are looking to the same internal experience as you create for your customer as well. [00:19:10] Speaker A: Yeah, absolutely. And I think that that's something we're hoping that we, you know, get out of doing this enablement, like company wide too. Is that okay? We may have ideas that we could use in our own product as well, so. [00:19:24] Speaker C: Wow. So it's the internal external combination and looking inside and outside. Fantastic. And yeah, AI was going to be a question that I'm going to ask you anyway, so I'm glad we covered that because we cannot possibly talk about all of the things without like, finishing on AI. So you, you captured all of that, which is fantastic. Any, any last words of wisdom, lessons learned that you want to share with with people as they're listening in? [00:19:51] Speaker A: Maybe one of like the biggest lessons I've learned is a best practice doesn't always mean it's the best practice for your business. [00:19:59] Speaker C: That's perfect. I mean, we always say too, that it used to be that you could do HR around best practices and everybody was looking to do what GE does, or then everybody was trying to do what Google does or anybody. But more and more it's so contextual. It's so related to what, who you are as a company. Right. [00:20:19] Speaker A: Yeah, exactly. We don't talk enough in HR about like just experimenting with new things that people haven't done. It always feels like we're trying to reinvent something that's already there. And it's like, well, if that, if nobody likes that, why don't we do something different? [00:20:34] Speaker C: That's true. That's true. Happens all the time. And I think we have plenty of things that nobody likes and that are ripe for reinvention, certainly in the HR area. So I love that. [00:20:46] Speaker A: Yeah. [00:20:47] Speaker C: Well, Hali, this has been such an amazing conversation. Thank you so much for your time. I really liked learning from you and sharing what you're doing with our audience, so thank you. [00:20:57] Speaker A: Yeah, thank you so much. It was great. [00:21:02] Speaker D: Thanks for tuning in to this episode of the what Works podcast. I talked with Helly Condon, Chief people Officer of Chili Piper. Hali give really practical advice how to build a strong connected culture in a fully remote global company. I appreciated how she uses HR tech like Hibob to streamline HR processes and support employees across 36 countries. Making remote work both personal and efficient. Her focus on experimenting with AI and empowering employees to use new technologies shows how innovation can start anywhere in the organization. And a reminder that best practices aren't always best for every business is a valuable takeaway. Sometimes the best solutions come from listening to your people and trying new things. Thanks for listening. Until next time, keep pushing the boundaries of what works for your company.

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