Managing a small team on a global scale

What's it like managing a team of 55 across 17 countries?

Headshots of Jen Paxton and Rhys Black on graphic

Welcome to New World of Work: a podcast exploring the new frontier of the modern workforce. In each episode, we’ll hear from some of the world’s best and brightest people and culture experts on the cutting-edge topics HR professionals are most interested in today, explored through a global lens.

Episode description

It’s important for companies to create a working atmosphere where everyone feels supported, included, and comfortable with collaboration, but this can become a challenge when team members are living on opposite ends of the world in separate time zones and with a diverse mix of cultural nuances. In some ways, striking the perfect balance can be even more challenging when it comes to managing smaller teams or startup settings that may not yet be equipped with all the infrastructure needed to operate smoothly. In this episode of New World of Work, Rhys sits down with Jen Paxton, the VP of People at Smile, to discuss the challenges of managing a global team. Jen shares some of the learnings and insights she’s gained while helping Smile grow, support, and manage a team of 55 across 17 countries.

Episode transcript

Rhys: Welcome to New World of Work: a podcast exploring the new frontier of the modern workforce. 

I’m Rhys Black, Head of Remote at Oyster, a global people operations platform making it easier than ever to build a brilliant team on an international scale.

On New World of Work, we’ll hear from some of the world’s best and brightest people and culture experts on cutting-edge topics that people operations professionals need to hear today, all through a global lens. 

Join us as we navigate this new world of work together and learn more about each other along the way. 

Managing a team that’s spread across the world is no easy feat, and many of us are still looking for the right approach as we navigate this new world of work together. As people operations professionals, it’s our job to set the tone for the company culture, while ensuring employees are happy, fulfilled and productive.

Creating an atmosphere where everyone feels supported, included and comfortable with collaboration is paramount. But this can become a challenge when team members are living on opposite ends of the world in separate time zones with a diverse mix of cultural nuances.

The shift to remote work requires significant investment, and the reality for smaller companies is that they are navigating and maintaining remote infrastructure with less resources and just as much complexity.

In some ways, striking the perfect balance can be even more challenging when it comes to managing smaller teams. On today’s episode of New World of Work, I’m sitting down with someone who knows all about this. 

Jen Paxton is the VP of People at Smile. She joined us on New World of Work to share some of the learnings and insights she’s gained while helping the company grow, support and manage a team of 55 across 17 countries. 

Jen kicked off the episode by sharing a bit more about herself, her career and her role at Smile. 

Jen: Yeah, so I, I started my career off actually in the startup space. So 20 I guess. Twenty thirteen. So a little bit less than 10 years ago when I took that kind of plunge to join my first startup and so on to say I'd say like I'm, I'm a startup junkie at this point. So I've helped companies grow from three to to three hundred and maybe a little bit higher than that as well. And then how did I end up with a smile? I actually it was on the heels of an acquisition that I was part of at my last company, Privy, and I was thinking about kind of what was going to bring me the most joy and what I wanted to do next. And I I wanted to go back into another startup and grow it again and and also experience a new challenge that I hadn't faced before, which was scaling a global team.

Yeah. So Smile power is actually eighty thousand ecommerce, loyalty and rewards programs and so that's all over the world. And just to give you an idea, a word program is like the Starbucks kind of VIP. So a smile is a fast company. We're headquartered in Kitchener, Canada, but when it hit, the team actually went fully remote. So we are 55 employees in 17 countries as of now. [00:02:06][29.1][00:03:45] So about 50 percent of the employees are still in Canada, but they're actually spread all over a different providences now. And then we have one person in the Caribbean, about seven percent better in Asia, and then the remaining 30 percent are actually spread equally across UK and EU as well as the United States. And then South America has been a huge hiring for us as well.

The smile situation pre pandemic was that majority of the employees and actually if you think back to like twenty, twenty, twenty smile was around thirty employees at that time and they had about two, two or three remote employees and that was, that was, they were all in really all in the kitchen or Waterloo area and Canada previous to the pandemic. [00:03:02] Yeah, so I wasn't working at SMIL pre pandemic, but I do have stories from folks that were working at SMIL Pre Pandemic and people are working very synchronously. They were mostly overlapping on their time zones and going into the office and having in-person meetings. FLAC was still very prevalent, but it was definitely more, more in-person engagement then of course, what we have now.

Rhys: Smile has seen some major growth and changes over the past year and a half. 

With the wild ride we’ve all been on since early 2020, it’s not hard to see why. 

Most companies have had to change up their approach at least slightly since the pandemic, no matter the size, structure or industry they operate in.

Given the intense growth Smile has seen in a relatively short time frame, I was interested to learn more about their approach to people operations overall, and how Jen has pivoted her strategy to tackle any challenges that may have come up as a result of these shifts.

Jen: What is smile's approach when it comes to people operations? I would say that we are not only there to this support kind of the smile employees, but we're also there to educate and to and to kind of push them. Help them to grow from a purely budgetary perspective. I, I think I mentioned this a little earlier, but I really love that coming in. I didn't have to say, like, hey, I need this hat counter, that headcount coming in. They were like, hey, what do you need? Like, whatever you need, like, let's make it happen. And and I really appreciated not having to have this, like, budget battle in conversations right off the bat. They're really investing in the infrastructure to help us scale from a people perspective. So I think that answers your question, but let me know if it doesn't.

Yeah, I mean, how do you think of how the pandemic changed our approach to hiring, And so us going fully remote actually gave us, I would say, a pretty stark advantage since we weren't limited by location, we could source and engage really the best talent no matter where they lived. So I'd say that it actually helped us almost like supercharged our hiring and and help us to to really find people that maybe wouldn't have been exposed to if we weren't hiring all over the globe.

Yeah, I feel like sharing all my secrets. Right. So it's finding great potential in different areas. We we found an untapped market in South America. So Brazil and Colombia for our engineers have been amazing. Just the the amount of of talent out there and just all of the candidates throughout the entire interview process had really blown us away. So I would not to completely spell the secret sauce, but I'd say that I think South America is going to be a pretty hot market for raw talent as a start up scale.

Rhys: The pandemic presented a huge opportunity for Smile as they were able to expand their search for talent to the entire world, rather than being confined to a somewhat limited talent pool operating out of the small city of Kitchener, Ontario.

This shift in perspective helped the company “supercharge” its hiring practices, which ultimately gave them a major boost in terms of scaling more quickly.

This global approach to hiring definitely presented new challenges from a people ops perspective, but considering the benefits of building an international team, it would seem it’s well worth the additional planning and creative thinking required.

I was interested in some of the challenges Jen had encountered managing a small team on a global scale.

Jen: What are the challenges that I was presented with joining to smile? one of them actually was that they had already started scaling. You know, they had I think they were in 16 or 15 countries when I first joined. So the amount of structure that they had was was not really there was just kind of like, let's hire somebody here, here and here, and then we'll figure out, like, how to support them after. And so I think for for me coming in, I was I was kind of tasked with this total rewards strategy. And how do we build that equitably for everyone around the entire globe? And then going into that, I'm going to be doing a lot of performance reviews. And then the other thing I think that is just kind of coming up more and more is how do you continue to build that sense of belonging for a fully distributed remote team where it might not be natural for people to to make those connections? 

Yeah, and I think it really depends. Like, our our smaller team is actually quite complex. I think we're in like 10, 10 plus time zones at this point. So getting overlapping meetings is in, I guess, overlapping means where everyone is at the same meeting live can be a challenge. So I think that one thing that we're working on is how can we actually work on a project as a team, but not have that space to work at the exact same time of day. So we're actually leveraging a tool called Thali for us. Our merchant experience team actually just did an entire project where they worked completely asynchronously using using Volly as their communication tool.

I'm a startup junkie at this point and yeah, well, I think one of the parts that probably comes in is there are more jobs to be done than there are people. And so you have a lot of at least speaking from personal experience, a lot of context watching. So my day can be well, I guess I'll just take take yesterday, for instance. So I was processing seeing a payroll change within our our contracting. I also had a monthly manager training that I was running. I had one on one with my team. I had actually had some sourcing that I was helping our director of talent out with. And then I also had preparation for this conversation as well. So I think that there's lots of different things that you'll be you'll be doing and working on and can pull you into multiple directions, whereas if you have a bigger team, usually have more focused areas where you're really going to just dove dove deeper rather than having kind of this spread thin, broad kind of atmosphere.

It it really is going to depend on our our hiring and kind of where we go from here, because I'm I'm a really big fan of from the people outside setting up that infrastructure. Well, to support the team, you are going to have not the team you just have right now. So coming into smile, you know, I was really excited because we were 50 50 people and I already had a team of two as well. So we could start to try to do some of that specialization right off the bat. But as we as we're growing and we're seeing kind of gaps on our team, I think we'll start to have more established lanes. You know, hey, you're going to take ownership of employee experience. You're going to take ownership of learning and development. You take ownership of the talent and recruiting side and the player branding side. So I think that'll that'll be really great to have more dedicated lanes for for people as we as we scale.

Rhys: As anyone who has worked in a startup environment knows, wearing many different hats at once is a skill that becomes invaluable as you grow and scale the company.

Jen noted that as Smile continues to grow, part of her approach will be to establish more firm guidelines around each person’s role.

In turn, this will help the company stay organized and run more efficiently, while supporting team members as they grow, improve and hone in on the specific areas they’re passionate or curious about.

One of the ways Jen is accomplishing this is by leveraging the appropriate technology and tools needed to manage a team effectively. 

However, the process of putting these systems in place hasn’t been without its own unique set of challenges.

Jen: Yeah, so it's it's funny, like just thinking, thinking about kind of my first we get smile and the technical challenges that I saw right off the bat. Smile is really good at documentation and putting kind of processes down on paper. However, there wasn't a person here to look at any of the old processes that had been put down on on virtual paper. So we we as notion is kind of our internal wiki. And so coming in as a new hire, I had thousands of N pages that I could potentially get into as well as way too many channels. So it was it was very tough, I think, to just virtually figure out what do I need to actually invest my time in versus maybe I don't need to explore this. And so from a from a documentation perspective, I think someone who has kind of that that gatekeeper or that like that farmer who can go in to your your internal wiki and say, hey, this is relevant or this isn't relevant and identify, you know, how does it need to be updated or completely archived would be helpful.

We have a an actual onboarding checklist. Now, with specific links to the notion pages that we want new hires to to get into, and so one one part of that is any kind of also pre onboarding that we're trying to do. So a new hire. Once you've accepted the offer, we were going to send them a pretty much like a PDF handbook of all the things they might need to know about Smile just to kind of get them up and running. And so a lot of those specific notion pages on how do we work or, hey, how are the tools like how do we use our tools specifically here or where do you go to find X, Y and Z are all going to be baked into this nice PDF. We use that. I'm actually building it out right now. It's in Canada. And and so they're going to be able to have all of that information ahead of time so that there's not as much back and forth with our employee experience. Specialist Koner, just to understand, hey, where do I go for this or how do I find this? And then when they get here on day one, they have the onboarding checklist in Knowshon where they can go and look at specific SMIL articles on the company. Again, a nice refresher on how we work in tools are in that right now as well, just so they are starting to get acclimated and know exactly what to focus their efforts on in week one and week two. 

Yeah. Yeah. So it and it started off because we have different different specific benefits for our Canadian employees versus our non Canadian employees right now. And then we wanted to kind of distill it down into, hey, what are the specific benefits that we offer in your country and are there other are there other specific things that you might need to know? Like how do you submit expenses? When does payroll happen for you? How do you log how you log your PTO? We we have unlimited you take what you need PTO, but we still want to make sure we're tracking it. And this is why we want to track it. And the additional part of that is going to be a welcome note from Mike, who is our CEO as well. Just to have people feel that sense of belonging in that welcomeness just even before day one. 

And this also is actually very complementary to the live sessions that we do. But again, being asynchronous, we're trying to go more asynchronous. We're actually trying to move a lot of those live sessions to also be recordings so that we could have a more kind of one to one to many approach to sorry, that was so much to unpack right there.

Yeah, I would totally agree with that. The other thing I will say that we're we're starting to think about is what all should be in in Knowshon, kind of in our wiki and what all should we actually have and maybe a different place and kind of trying to strike that right balance as well. Right now, notion has been kind of our main our main stream for knowledge or mainstream for collaboration even. But our teams are now starting to branch out into tools like Mirro as well. And I'll let my team actually this Trello for project management. And so we we talk about every every morning we have a standoff and we talk about, hey, like what are we going to work on today? And we go to the Treleaven, look at it. I could see that shifting even more asynchronously as well at where we don't really have to have a stand up for Trello, but we have to say, hey, like, this is what we're going to work on today kind of thing. 

Rhys: Feeling connected to colleagues when they live on the other side of the world can seem impossible or unnatural at best, but with the right practices, and more importantly, mindset, it’s certainly an attainable goal.

Knowing that Jen and her team have mastered the dynamic of hiring on a global scale, I wanted to learn more about some of the benefits they’ve seen from taking this approach overall.

Jen: Oh, so I would say some of the advantages to hiring internationally are that you are not cutting cutting your talent pool at the knees. You know, you really are able to hire wherever you would like. And you can actually you could basis on like, hey, there's a really cool company that is based in Australia, I'll just say. And they have you know, they have people that are doing things that we really want. So, for instance, on the product side, if we are trying to launch an ecommerce marketplace or a platform or or a specific kind of consumer based launch, we can actually target people in different countries at specific companies, maybe Widmaier to come work for our team, whereas if we weren't actually global, we'd be kind of stuck in kind of this this one kind of pool of people. And we might not even be exposed to people in a different country.

Yeah, I actually would. We are thinking about a global scale for that. We're thinking about time zones. You're right, because we on our support team in particular, we are 24/7. And so we need to have people who are up and working during those specific times. Whereas if we had people that were here in the US and actually I've hired support teams that have done the like 11, you know, 11 p.m. to seven a.m. shifts in the US. And it's very challenging to find those hires here or people that are willing to do them. But if you're hiring somebody, you know, in a different time zone across the way, it's like they're nine to five. Right. So it can be a lot easier from a scaling perspective for that.

Yeah, when you're talking about kind of it permeating to other parts of the organization, I was thinking about kind of our site reliability engineers and how we we actually targeted, you know, India as a place because we have people in Kitchener. We have people actually we just hired a person in Ohio and now we have one a person in India as well. So now we have a little bit more coverage so that if something goes down, we have somebody that is going to be up and already monitoring the situation there as opposed to someone who is getting, you know, a ping via a pager duty like 3:00 a.m. in the morning and like having to wake up groggy and having to to fix the situation.

Rhys: With team members located all over the globe, something else companies can take advantage of is the ability to support their customers around the clock, which according to Jen, has made scaling much easier for Smile. 

I asked Jen about any challenges that have come up as a result of this asynchronous working environment, and this is what she had to say.

Jen: Yeah, I feel like having an fully asynchronous team is still a work in progress for us. So we have our head of design out in Spain. We have our VP of product in the Toronto kind of Kitchener area. We have our VP of engineering out in the United States on the West Coast. So we're we're definitely spread, I would say, with all of the different time zones. And actually, we hired a product manager in India as well. And so all of those teams are really starting to understand how can they work asynchronously when it is such a collaborative environment. And and kind of one of those things where it's like if an engineer has a question about a prioritization, what what do they do if they can't slack the product manager because the product manager has gone to bed? So what what do you do on that case? I'd also say from the engineering and product side, they're also working on kind of working hours, like what is what is going to work for them and see what happens. Some other companies that have done this previously that I've seen actually work that way. We might get why why I say it's a work in progress is like we might go this way one day is having specific teams be in specific locations. So if we have a product manager in India, maybe we have that specific team also in India working on a project. So they have at least one less level of complexity there.

Yeah, I'd probably say start off smaller than we did. We kind of went it's you live and you learn, right? So like I came in to like the Wild West, and that was the challenge I wanted. Right. But but I think if I had to do it all over again and I was thirty people, I'd say, let's focus on a few specific hubs, see where we start to get some really great talent and invest in those. Keep the door open for other locations as well, because you gel again. You don't want to cut your your talent pool, but really start to build up structure in a few different places. The challenge I'm running into right now is how do we build equity throughout kind of compensation right now? Like, do we go that route? Do we go the market based route? What do we do as far as accounting for the very inequitable kind of paternal leave policy in different in four different locations? Because we're all over all over the map on that one as well. So I think if you if you can if you can tamper down the complexity just a little bit first and kind of get your your plan in place, then that's really going to help you to scale to multiple other locations after you get that plan.

Rhys: Jen’s advice to zero in on a few locations as your hiring pool first, makes a lot of sense. 

While the idea of building a global team with employees in every country may sound glamorous and exciting, it’s certainly not without its logistical challenges and pain points.

For hiring managers, it’s best to start off slow by gaining traction in a few key areas where you already have a proven track record of success before expanding to other countries to explore. 

Jen noted that Smile took on a high volume of international hires fairly quickly, so I was curious to know how this might have affected the existing company culture, if at all.  

Jen: Yeah, I, I think that, you know, adding more global talent has helped our culture to evolve. And I think even. Be more open, you know, since we have people that work in multiple countries, that means that all of us are exposed to other cultures and other languages. And this can actually be a huge challenge on just how people express themselves or how they're giving feedback. I mean, oftentimes you might not even be used to a specific culture and maybe misinterpret something from an individual. One thing that we did was we we actually put a notion page up about understanding specific cultures and how people actually either give feedback or how they like to have context when making decisions. There's a really good book called The Culture Map by Aaron Meyer in that there's a few different visuals on that, that basically pinpoint specific countries to indirect or very direct feedback and context as well. And I think that that helps you to at least start to recognize the the very broad spectrum that we we have smile at least at least starting to understand it will help you to to understand how how can you actually work with it instead of against it.

Yeah. So we we've still not like not not really perfected what it's going to look like as far as like do we try and get a time where everybody can be together in one place? We do have Monday update meetings for everybody at the company to attend or be at asynchronously. In addition to that, we have been trying to build kind of like those water cooler, water cooler connections as well. So we use Donat for that. And that can be really helpful for people that are maybe not interfacing with each other. The other cool like combination with with that is if you get paired with somebody that is like that doesn't overlap in your time zone, but your your paired and donut, you can actually send them a volley back and forth as well to get to know them. And so that's actually when I joined the company, I had a good bit of those that I would have a volley back and forth front with with the the employee just to kind of get to know a little bit more.

Rhys: One thing many of us are missing while working remotely are those “water cooler” conversations about weekend plans, TV shows or just catching up on the office happenings. 

This is where building a strong company culture through the right mindset and regular touchpoints comes in.

Jen’s comments around team building got me curious about the hiring strategy Smile will be taking moving forward.

Jen: Yeah, when we were thinking about our own strategy, I honestly I think it's going to be a blended approach. We do need to start adding areas of focus. You know, if if there was a way to have have your brand be completely global without being a massive, massive company, then that would be amazing. I would love to uncover that and kind of crack that nuts. But as far as you know, people seeing our jobs, it really depends on, you know, how are they even going to know that smile exists if we're not actually advertising or if we're not on on remote sites to make that happen. So I do think that we'll we'll do a little bit of investment in some specific kind of cluster areas, especially especially South America. But then at the same time, if we have someone come in like kismet or like even maybe a referral that's coming in from a location that we're not in yet, bear in mind, like 17 countries, it's like a good amount of countries as well to like start to think about your your candidate pool from. But I don't want to ever close the door. We actually have a higher that will be starting shortly. That is will add to it maybe in 18 countries after after they start. And I'm super excited about that. But I also have some. Know like it's not there's got to be a point where you're like, this is enough, like I think I think we're OK for right now to to manage. So we'll see.

Yeah, I haven't implemented it here at SMIL, but at previous companies, I've started to look at specific local job boards and I'd start to make actually connections when when one of my previous companies actually had a Duplin location, I invested in actually making a connection with a specific technical university over there so that we could start to get their technical talent and they would know they would know the company really well. So I think that that would be a really a good strategy for us to implement over here. Whereas if we are looking to to scale and to grow, there are either I mean, we're already on the remote job board. So I think that, like, we have that covered. But as far as getting other exposure into other other maybe untap job boards or other maybe specific like in the States, they would have like meet ups would be kind of that organization or partner organizations to get into. I think that would be really helpful for us as well.

Rhys: After a great conversation with Jen, I wanted to know what’s on the horizon for her and for Smile.

Jen: I feel like I'm, as I mentioned, like wearing a lot of hats right now and. But what what I'm going to try and focus on the next really two to three months is defining our compensation plan, which is our philosophy and our strategy, and then also implementing career ladders and then performance review. So it's kind of a tiered approach there where we define how we're going to pay people and then talk about what are the levels that we have here and what are the growth path for people. And then we're going to give people specific feedback on, hey, here's where you're at and here's where you can get to. So those are the yes, I'm going to be working on.

Rhys: There you have it—another great conversation with an inspiring people operations professional who is helping to change the way we look at the workforce today and shift the narrative in a positive way.

After our conversation, a few key insights stood out to me.

First, Jen and the team at Smile are clearly taking full advantage of all the tools and technologies available to make everyone’s job run more smoothly. She mentioned using tools like Volly to facilitate communication across time zones, and I also loved her idea about sending new hires a full PDF handbook so they can review the document with minimal distraction from other digital tools used day to day in the company.

Jen also mentioned some of the benefits of hiring internationally versus limiting the talent pool to just one country or region. As a 24-hour e-commerce company with international operations, hiring people in other time zones has been a game changer for Smile. Overall, viewing the globe as your talent pool maximizes the potential for discovering the best possible talent for each role, which will in turn, optimize your team and ultimately diversify the company culture.

Finally, although hiring internationally comes with several benefits, Jen noted that in the future, Smile will be taking a more focused approach by doubling down on certain talent markets with excellent opportunities. 

As always, balance is crucial, and building the ideal team for your company is no different. Finding the sweet spot between hiring internationally and building a strong community is essential, and it’s great to see people operations professionals like Jen rising to the challenge.

Thank you for listening to New World of Work, the podcast exploring the new frontier of the modern workforce through an international lens. We hope this episode served to expand your horizons and open your mind to a new perspective.

Be sure to subscribe, rate and review the podcast so we can reach more listeners.

I’m your host, Rhys Black. See you next time.

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About Oyster

Oyster is a global employment platform designed to enable visionary HR leaders to find, hire, pay, manage, develop and take care of a thriving global workforce. It lets growing companies give valued international team members the experience they deserve, without the usual headaches and expense.

Oyster enables hiring anywhere in the world with reliable, compliant payroll, and great local benefits and perks.

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