PODCAST: Company Retreats Bring Big Benefits for the Small Remote Software Company Wildbit

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In our latest podcast episode, we speak with Natalie Nagele, co-founder and CEO of the software company Wildbit, about why company retreats are so important to her team.

Company Retreat-1

In our latest podcast episode, we speak with Natalie Nagele, co-founder and CEO of the software company Wildbit, about why company retreats are so important to her team.

The benefits of company retreats are well-known. Not only do retreats get employees out of the everyday monotony of office life, but they also serve as a great way to team build with your colleagues.

But what about the advantages for a small group that works remotely? For Wildbit, a Philadelphia-based software company at which more than half of their 30 employees work from around the world, they are twofold.

In our latest episode of “Outback Talks: The Employee Engagement Podcast,” we speak with Wildbit co-founder and CEO Natalie Nagele about the role that retreats play at the company, as well as the complex yet considerate thought process that goes into planning these trips. Listen to the episode below, or keep reading for an overview of our discussion.





Valuable Face-to-Face Interactions 

"Our retreats have always been one of these things where new people come meet people who’ve been there for a while and you walk away from that meet having such a keen understanding of who everybody is," says Natalie, who created the company with her husband, Chris, 18 years ago.

Wildbit, which produces multiple products that solve problems for software development teams, has always been remote — their first employee who wasn't a founder was based in Romania. Their inaugural company retreat was in 2007, in Cyprus.

"It was not necessarily intentional in building culture and community,"
Natalie recalls, about the trip. "It was like, ‘we work together all the time and we’ve never met each other, so let’s find a place we can all meet and hang out.’ And when we all got together, we realized how important that was for our personal relationships, and understanding who we are as people, and giving that human element to the work that you do in an asynchronous way. On the internet, with chat, video calls, and all those things, you lose some of the nuance of an individual. One of the benefits of working together in an office is you start to pick up on people’s personalities, and it’s much harder to do via chat."

The company has run their annual retreats since, using it as an opportunity to have invaluable face-to-face interactions, along with an exciting “getting to know each other for the first time” element that comes as a result of not working together in an office everyday. Not only does this build rapport between colleagues, but it also helps to develop company culture.

Important Planning Sessions  

The purpose of Wildbit's retreats isn't to socialize. It's a special time allotted to work and roll out important things that require the whole team to be together in one room, in person. For most companies, this can be an important part of a retreat – for remote ones, it’s an imperative focal point, because employees rarely get the opportunity to be in the same place at the same time.

"The majority of our time is spent in some type of planning," Natalie says. "That varies with year-to-year, depending on what we need. After a really crazy busy year, we might do more social things than not, but either way, we don’t bring spouses or partners. It’s just the teams, because we are working. We can better manage our time together to plan and strategize the things that are necessary for us to make big decisions that are harder to do remotely.

I’m a huge proponent of remote work. There’s something about dedicating a day, sitting on a couch. That physical presence — that’s a place where we do very big things, whether we are changing the values, restructuring, or trying to thought-process or something like that, we’ll roll that out during the retreat."


Thoughtful and Personalized Experiences

Planning, Natalie says, is “crazy complicated.” Wildbit starts planning their retreat about a year in advance, first taking date, budget, and weather into consideration. Location, though, is one of the biggest factors in the whole process, and a location that’s easily accessible for all team members to get to is paramount. Palma de Mallorca, Disney World in Florida, and Turkey are just a handful of their previous retreat spots. Their most recent was a ranch in Sonora, Texas.

"We try, actually, to stay away from big cities because our retreats are structured, so that we’re spending time together," Natalie adds. "So, we try to be a little bit more remote."

The company works with a broker who understands and can cater to the team's needs. Then, fine details like dietary preferences are ironed out. As a result, the trips are very personalized experiences with inclusive considerations for everyone.

"From a tactical standpoint, I think we learned over the years that as you bring more diverse people onto the team, you have to be thoughtful in things for everyone," Natalie explains. "Every year, we reflect and adjust and think about what we did well, what we didn’t do well, what could have been better, and just continuously iterate to make sure that when people leave, they feel like they were taken care of.

There’s a lot of behind the scenes thinking: who stays with whom, who shares a room, to what the meals look like and how we respect everybody’s dietary restrictions, to activities and what will make everybody comfortable so that we don’t do an activity that makes somebody really uncomfortable for whatever reason. We do a lot of the behind the scenes thinking to make sure that it’s a positive experience."

You can tune into our interview with Natalie above to hear more from her, or download the episode by subscribing to our podcast, "Outback Talks: The Employee Engagement Podcast," on Spotify, iTunes, Google Play, SoundCloud, or Stitcher. See the full transcription of the episode below. 


Learn More About Company Retreats 

Check out the free, downloadable, 60+ page resource, Everything You Need to Know About Planning the Ultimate Company Retreat for more expert advice on how to prepare a successful company retreat. For even further support, just reach out to one of our Employee Engagement Consultants.

Get in Touch



Yasmine Shemesh (YS):
Hey everyone, welcome to “Outback Talks: The Employee Engagement Podcast.” This podcast is produced by Outback Team Building & Training – a leading team building, training and consulting provider for organizations across North America. I’m your host, Yasmine Shemesh, and on this very special two-part episode, we are talking about company retreats. We have a couple of amazing guests who will be joining us who have some pretty valuable insight to share about how and why they do company retreats.

On today’s show, we are speaking with Natalie Nagele, who is the co-founder and CEO of the software company Wildbit. Most of Wildbit’s team actually works remotely – it’s something they’ve been doing for 18 years – and so retreats are a very important event for them. Natalie kindly sat down with me to discuss the role that retreats play at Wildbit, the thought process that goes into planning these trips, and also what kind of things they do at their retreats.

YS: Welcome! Thank you for joining me today!

Natalie Nagele (NG): I’m happy to be here, thanks for having me.

YS: How’s your morning going so far?

NG: Great! It was a very exciting week for us, so, it’s good.

YS: That’s great! Yeah, you were saying you guys had your offsite with your leadership team.

NG: Yeah, we did that last week and then this week we kind of kicked off as a whole team. Just planning, you know, annual goals, stuff like that.

YS: That’s awesome! So, we’re talking about company retreats today. First of all, can you start off by just telling me a little bit about what Wildbit is and why you and your husband, Chris, started it?

NG: Sure, yeah. We are a software company, we’ve been operating for 18 years. We have multiple products – subscription products, software service. And they all solve needs for software development teams – that’s where our sweet spot is, that’s what we love to work on. Around 18 years [ago], my husband, Chris, started it as a consultant practice and I think the why is really because we wanted to, you know, solve challenges with great people and do it on our own terms, and experiment with what that means. And we’re still doing it after 18 years!

YS: That’s wonderful. Yeah, and you guys have a lot of branches that come from Wildbit, from the parent company.

NG: Yeah, so we have multiple products that we work on all tied back to solving problems for software development teams. We have an email product called Postmark, we have a merchant control product called Beanstalk, and we have a new product on the way called Conveyor.

YS: That’s great! So, I know Wildbit has a lot of employees who work remotely – which is very cool and, especially in today’s day and age, it makes sense in a lot of different ways. And you guys have been doing it for a really long time, which is wonderful. And so, in turn, your company retreats have become an important part of the company’s philosophy. So, why are these trips such an important part of the way the company works and the way that your employees work?

NG: We started off as a completely remote company, so we’ve been remote all 18 years. The very first person who worked at Wildbit that wasn’t a founder was somebody in Romania, and it kind of worked from there. So, for us, the very first retreat in Cyprus was basically not necessarily intentional in building culture and community. It was like, ‘we work together all the time and we’ve never met each other, so let’s find a place we can all meet and hang out.’ And that was the first time.

And when we all got together, we realized how important that was for our personal relationships, and understanding who we are as people, and giving that human element to the work that you do in an asynchronous way. On the internet, you know with chat, video calls and all those things – but you know, back then we barely did any video calls, so really just chat – you lose some of the nuance of an individual, you know, whether if they are in a good mood, whether they’re in a bad mood. One of the benefits of working together in an office is you start to pick up on people’s personalities and you can sense things, and it’s much harder to do via chat.

Our retreats have always been one of these things where new people come meet people who’ve been there for a while and you walk away from that meet having such a keen understanding of who everybody is and what they feel like and what they like.

YS: I would imagine, too, that dynamic must be really interesting because – especially if you’re not physically with each other on a day-to-day basis – you almost have that excitement when you’re meeting new people, even though you may talk to each other every single day. But when it’s a face-to-face interaction it’s, you know, it’s different. So I would imagine that, yeah, there’s probably a really cool “getting to know each other for the first time” element that comes into play.

NG: Absolutely. For us, I mean, we work very close together, we’re still a small enough team where everybody kind of knows each other and, I think, truly cares about each other. So, having the time to spend together – especially when a lot of people work from their homes, so they don’t have that camaraderie on a daily basis from their co-workers, they have to create that in their own ways.

YS: Right.

NG: So, for us, it’s very much a planning retreat. We do a lot of work, but there’s also a social aspect, [where] it’s just better to be around together. It’s really just to continue to understand each other’s personalities and the nuances that are so much harder to grasp in shorter conversations.

YS: Yeah, for sure. So now, how do you guys plan these things? What goes into that whole process?

NG: It’s crazy complicated. Julie, on our team, who heads up Team Happiness, one of her bigger projects of the year. You know, it’s 30 people coming from a bunch of different places booking flights, booking a space is big enough, and planning transportation and all these things. We plan and find a date that works for 30 different families. So we start pretty early, at least setting the date so that we can make sure that it’s on everybody’s calendar. We use a broker who helps us locate spaces that are big enough. We don’t do hotels – we try very hard to be able to eat meals together, hang out together. We work very hard to find spaces that are feel more like a home.

She starts about a year in advance, thinking about the date. And then maybe somewhere, you know, eight months out, she starts searching for space. But it’s a tremendous amount of work.

YS: You were saying that there is time set aside for work, as well. So, going into it, do you have a specific set of goals that you plan for to achieve for the retreat?

NG: Our retreats are not vacations, our retreats are work. So, the majority of our time is spent in some type of planning. That varies with year-to-year, depending on what we need. Some, you know, after a really crazy busy year, we might do more social things than not social things, but either way, we don’t bring spouses or partners. It’s just the teams, because we are working. We can better manage our time together to plan and strategize the things that are necessary for us to make big decisions that are harder to do remotely.

I’m a huge proponent of remote work. There’s something about dedicating a day, sitting on a couch. That physical presence – that’s a place where we do very big things, whether we are changing the values, restructuring, or trying to thought-process or something like that, we’ll roll that out during the retreat.

YS: So it’s really an opportunity for the whole team to just come together and get on the same page.

NG: Yeah. I mean, we absolutely try to balance that with social. We’ll go on trips. Usually we try to do six nights and five whole days. We come up with a pretty direct, specific schedule where its: ‘here’s where we’re meeting, here’s breakfast, here’s lunch, you know, here’s dinner.’  We were in Orlando, Florida a couple of years ago, and we went to Universal [Studios], we went to the Magic Kingdom. So, we add social time and we end pretty early. We end at like, 3, and we move into, you know, Happy Hour, hanging around. Depending on the house – we stayed in a house that had bowling alleys. Last year, we were in Texas on a big ranch and we got to do other things. So, you know, it depends. We’re all pretty tired by the time we get back.

YS: So now, how do you decide on the location? I noticed from looking at your site and the list of all the places that you guys have gone, you’ve been to some pretty amazing parts of the world. What kind of factors influence the decision of where you choose to go?

NG: You know, they change every year because the location of our team has changed over the years. We work a lot with folks on the other side of the ocean and, so, I think cost plays a huge factor. Cost and weather. And we try, actually, to stay away from big cities because our retreats are structured so that we’re spending time together. So, we try to be a little bit more remote and we look a lot at flights and what’s the easiest way to get to it and, you know, how complicated is it to get there.

YS: And you guys went to Sonora in Texas last year too, right?

NG: Yeah, it was a great ranch. And they were able to accommodate just us, which was really lovely. You know, we look at things like how many bathrooms, how many rooms can we squeeze into, you know, that kind of [thing]. There’s just a lot of factors. We work with a broker who we used last year and we were happy with, so they’re going to help us out again this year.

YS: That’s great! Yeah, they probably have a good sense of what you guys are looking for.

NG: Exactly.

YS: So, do you have any memorable experiences or any highlights from your last retreat?

NG: Yeah! We try to do a lot of really special things, and most of it comes down to how much quality time we can spend with the team. This last retreat we got to do a lot of really deep thinking and then we were also on this really great property. It was warm and we got to do these four-wheeler rides around the lake. It was huge, I forgot how many acres, but it was huge. And, you know, we got to meet some of the animals on the property and that was really special.

When we were in Orlando a couple of years ago, we were able to run around the park really late at night. They do an adult After Hours – as much ice cream as we could eat and just explore the park, and that was really fun for everyone. So yeah, it varies. We try to do stuff like that. I think the most memorable is always the relationships that are made and the quality time together.

YS: Absolutely. You know, we had our annual retreat and ours was late November. And it was my first retreat with the company and I’d heard so many things about it and so I was looking forward to it very much. And we had a good balance of work and play time, as well. But it’s true – the biggest take away was that you got to truly connect with the people that you work with everyday. And in a different way, as well. You could go and have a coffee with somebody and just, you know, have a nice deep conversation that you might not have the opportunity to do when you’re at work. It is those connections that you make that are the biggest highlight of these kinds of retreats. So, now, looking back to your very first retreat in Cyprus, to now where you are planning to have for the next one for the coming year, what kind of things have you learned about the whole company retreat concept?

NG: From a tactical standpoint, I think we learned over the years that as you bring more diverse people onto the team, you have to be thoughtful in things for everyone. So every year we reflect and adjust and think about what we did well, what we didn’t do well, what could have been better, and really just continuously iterate to make sure that when people leave, they feel like they were taken care of. We just really have to be thoughtful around that. There’s a lot of behind the scenes thinking: who stays with whom, who shares a room, to what the meals look like and how we respect everybody’s dietary restrictions, to activities and what will make everybody comfortable so that we don’t do an activity that makes somebody really uncomfortable for whatever reason. We do a lot of the behind the scenes thinking to make sure that it’s a positive experience.

YS: That’s great. Well, thank you so much Natalie. It was really lovely chatting with you, and this was great. Thank you so much!

NG: Absolutely! I love talking about it. Thank you so much!

YS: That’s it for this episode of “Outback Talks.” Thank you so much again to Natalie for taking the time to be on our show today, and stay tuned for Part Two where we will be speaking with Brian Ceci from the video production company, Noravera, about what retreats mean to his team.

Outback Team Building & Training helps organizations across North America build relationships through memorable team building, training, and consulting experiences, and our team has been recommended by over 14,000 corporate groups in the United States and Canada.

For more expert advice on company retreats, visit the downloadable resources section of our website at outbackteambuilding.com to download your free copy of “Everything You Need to Know About Planning the Ultimate Company Retreat,” and don’t forget to subscribe to our podcast on iTunes, Google Play, Stitcher, or wherever else you may listen to your podcast. Until next time! I’m Yasmine and this is “Outback Talks: The Employee Engagement Podcast.” Thanks for listening.