What Does the Future of People Operations Look Like?

A conversation with Oyster’s Head of Remote on how distributed teamwork is transforming the field of HR forever

By The Twist Team

What Does the Future of People Operations Look Like?
Illustration by Yin Weihung
Welcome to the Twist Future of Work Series — candid conversations with leaders who are building the “future of work”. Each month we’ll highlight a company that provides a product or service to support distributed teamwork, asynchronous communication, flexible workplaces, and a more mindful approach to work. Twist was built with these goals in mind, and each of our featured partners share in those values.

This month, we’re sitting down with Rhys Black, the Head of Remote at Oyster. A fully distributed team themselves, Oyster is an HR platform that helps companies employ teammates from anywhere in the world. Our conversation focused around how remote work is forcing a big change in the way companies manage their most valuable asset: their people.

Key takeaways:

  • People operations is quickly becoming a competitive advantage for forward-thinking companies, particularly for distributed and hybrid teams. HR is no longer seen as just a supporting, administrative function but rather a central, dynamic part of companies’ day-to-day operations.
  • Contrary to popular belief, it’s possible to create a strong team culture and sense of camaraderie remotely — both Doist and Oyster live that reality every day. But it takes a strong commitment to creating an exceptional employee experience.
  • Remote work has the potential to expand access to high-quality career opportunities beyond a small handful of large cities to anywhere in the world. Where you’re born shouldn’t dictate your job opportunities, and with today’s technology, it doesn’t have to.
  • Companies shouldn’t run before they walk when it comes to hiring remotely. For example, instead of starting out hiring someone halfway across the world without a process for creating a good experience for that employee, start within your own time zone. Or start within a single team and expand remote hiring from there.
  • www.oysterhr.com — An HR, payroll, and legal compliance platform that streamlines hiring across 180+ countries
  • Oyster Academy — Two remote work bootcamp courses: one for remote job seekers who want to build their remote work skills and the other for HR leaders looking to upskill their organizations for the remote future

What’s Twist? Twist is an async messaging app for teams burned out by real-time chat, meetings, and email.

You don’t need to use Twist to get a ton of value out of this newsletter and community. But if the topics we talk about resonate with you, there’s a good chance the app will too. See what makes Twist different →

🌎 Built asynchronously by the fully remote team at Doist

Full transcript:

Chase (00:04):

Hello, and welcome to the Twist Future of Work Series part one, I'm Chase Warrington, the Head of Remote here at Doist, and I've got a good friend of mine. Rhys Black from Oyster is joining us for the first episode in the Twist Future of Work Series. How's it going, Rhys?

Rhys (00:22):

Great. Great to be here. Thanks for having me.

Chase (00:24):

We're excited to partner with Oyster on this dive into the future of work generally, which we obviously both love and both work in. The focus of this particular episode, as you know, is really about diving into human resources, HR for short, and how that's changed as a function of remote work, as more teams are adopting remote work as the quote unquote future of work becomes the present.

Let's start really quickly with just a little introduction. I've kind of introduced myself - I'm here in Valencia, Spain, and I'm part of Doist, which is a fully remote team spread across 35 different countries, about a hundred different people, coming from all time zones. So we are all about remote work here, and we are the producers of Todoist and Twist. This is the Twist Future of Work Series, where we are really honing in on asynchronous communication and the future of work. Which is what Twist is here to support. So just like the people over at Oyster where you guys are also all about the future of work. Tell us a little bit about you Rhys and what you guys are doing at Oyster.

Rhys (01:45):

Yeah, sure. Hi everyone. So my name's Rhys Black. I'm Head of Remote at Oyster. Let me just quickly explain what Oyster does first. So we are an HR platform specifically for distributed teams. So, what we do is we make it really simple and easy for companies to hire people as full-time payroll employees, as well as contractors, anywhere in the world. So you can get access to the best talent in the world, not necessarily just the best talent in a particular geographic region. And we deal with everything from payroll to compliance to benefits and everything in between. In my role at Oyster, the Head of Remote spot, I touch a few different areas in the company. I kind of like to think about it as somewhat of a glue between other parts of the organization. Some of the areas that we tied together are, operations, people and marketing.

Rhys (02:41):

So on the operations side of things, it's really around the work that needs to be done differently or to be emphasized because we're a distributed team. So there's a lot of work there around building autonomy for teams and individuals and visibility for teams and individuals, so that it can work well across time zones and work cases for instance. So there's a whole load of work with knowledge management, project management, defining ways of communicating and collaborating and that space also trying to be as data driven as possible in this area, which can be somewhat more qualitative than quantitative. And then on the people side of things, it's the employee experience that creates. There are lots of great things about remote work and being a distributed team, but there are quite a lot of challenges too, right?

Rhys (03:29):

So we want to optimize for the really good things and mitigate or minimize those challenges. And really those two areas, the operations and the people side of things that culminates in our culture. So really the predictability and repeatability and the way that we do things as a distributed team and how that makes us feel. So that's that, and then partly because of the company that we are, we want to communicate a lot of this stuff externally. We want to be a source of inspiration and knowledge for our customers and anyone else that wants to listen to us. So I work quite a lot with our marketing team to do that.

Chase (04:06):

Yeah, you guys do a fantastic job of that as well. Your whole team's very active in the social world and the marketing teams are putting together great content. And I think that's why this is such an awesome collaboration here between Doist and Oyster, because we both just genuinely care about pushing forward, this future of work, right? We want people to have access to these distributed workflows. We want them to have the best practices that we're cultivating every single day and working hard at and testing. So it's important to both of our organizations to push that movement forward. And that's that's basically why we're here. That's why our roles exist to a large degree. And it's a lot of fun. It's great to pay it forward in that way, because I think both teams, and I know in your previous experience, my previous experience, where you have some growing pains, we've learned a lot and taken our lumps along the way, I believe.

Rhys (05:03):


Chase (05:06):

Well when we dive into what Oyster does in particular what do you think has changed in terms of HR, as teams have started to adopt more of a distributed model, and I guess, like setting the backstage a little bit, when you think about going from everybody working in office and pre pandemic, and even let's go a couple of years ahead of that, remote was starting to ramp up before the pandemic, it just got accelerated super fast, but all of a sudden, we arrived at this point where there are a lot of teams around the world saying, oh, I need to figure out remote now. And it's not just, how do we do zoom calls and how do we send a communication back and forth, but it's things like, how do we hire and fire and pay? And so, what has changed and, and I guess as part of that, what is Oyster doing to solve those pain points?

Rhys (06:10):

So this is a big thing. I think if I was just to start with a strap line for this whole thing, I would say that culture has become a non-negotiable I guess you could say, and culture has been thrust into the spotlight. So, if we were to talk about specifically People Ops teams as HR teams, you could potentially make an argument that these teams have been undervalued to some degree historically, and have been an administrative function, more of a supporting function for other parts of the business. And I've not really been able to step forward into that spotlight into the culture area. With the pandemic and with everything else, there has already been that progress moving forward.

Rhys (07:05):

We have this term HR, which has been around for a very long time, but there has been this progress towards a more modern people operations function. So it's to be this more holistic function, to be thought of as more of a competitive advantage, like thinking of your people is just as important as your products and everything else that your company offers. So that was happening already. And then of course, pandemic hit. We accelerated that by 10x. So, now we're at a stage where these teams that were already making this transition - various stages from being the more traditional HR to being perceived and getting the agency to be a modern People Ops team - have now also been tasked with being almost like a playmaker, a change agent within their own organizations. So, a pandemic happens, companies decide to go fully remote or decide to go hybrid and all of this, and the whole sphere of responsibilities around that largely, and most companies, I sat with their People Ops team. So, it's a great opportunity, but a very big responsibility.

Chase (08:19):

Absolutely. I think it's important to point out that a lot of people see remote and culture as on two different ends of the spectrum, as far as can you have culture with a remote organization? This gets challenged a lot, maybe as the big downside. You'll see some article that some CEO has written, ``You can't build team camaraderie in a remote organization," as if they really cared about the culture and the team comradery beforehand. And it's always a little bit funny. It is truly about the people and for the organizations doing this correctly, it is looking at your people as the greatest asset that you have. So, how is Oyster serving the needs of organizations that are moving to remote? And if someone doesn't know what Oyster does, how do you explain it to them? What's the elevator pitch - what does Oyster do to serve the needs of those customers?

Rhys (09:25):

So there is the core problem, but then I think there is a much larger problem with space around that that we are tackling. So, as I mentioned before, the basic situation, let's say a company will come to us and the situation that most of the time there'll be in is that they run an interview process. They have come across a candidate in another country that they absolutely love for dying to get them into their team. And they're confronted by the realities of, "Wait. How do we actually make this happen? How do we employ this person legally? How do we give them an equitable package relative to the rest of the company and not full federal to any regulations." So that's usually when someone will come to us and will say, "We have this person or this team that we want to bring on board."

Rhys (10:12):

So that is the core of this problem. It's how to employ them properly under the right labor laws for that particular country. Get them the right benefits, pay the right taxes, pay and deal with all of the complexity around that. And then I guess, clicking out one ring from that, you start to then get to things like the larger compensation elements, like benefits, healthcare, equity, these sorts of things, as well as, I guess you could say, learning and development and in that space that you can, in some ways you can think of us as like an outsourced HR concierge and a lot of ways that that will deal with not just the payment compliance points, but that bigger space around it. The term we use a lot of the time is talent enablement.

Rhys (10:58):

So those two words are important for different reasons. First one is we're talking about the talent, not the company. So we started pride ourselves on being talent-centric and being focused on the employee because really that's what aligns with our social mission. The most right. Our mission is to get people access to high quality jobs, no matter where they are in the world. So they don't need to move and get separated from family and community, or have a lackluster career, maybe where they live.

Rhys (11:30):

So we focus on the talent. And then the other part is that enablement, right? What needs to be done to enable that person along with their company to have an amazing working relationship with them. So I guess from, from the small core problem, all the way up to, to that, and that's why we run, for example, things like Oyster Academy.

Rhys (11:49):

So Oyster Academy is our training program where we have multiple training programs underneath the Oyster academy. One is for general remote workers that wants to understand the skills and knowledge and mindset that they need to have to be a great remote worker, alongside whatever their core competency is. As well as we also have a course for People Ops managers. So to actually help them be that Playmaker, that change maker in their organization. So there's a big space. When you say enablement, around that.

Chase (12:19):

It's a massive space. I mean, it's like geographically, even speaking, like you guys are doing this for people around the world and enabling people to acquire talent from around the world. Correct?

Rhys (12:33):

Exactly. Yeah. I lose track of where the countries we cover at this point. I know we're well over a hundred countries in terms of where we're employing and our customers are all spread around too, but there's basically no limits to that.

Chase (12:47):

Yeah, it's truly global. You guys are like a distributed global team serving the needs of global customers. It's a pretty cool little intersection you're working in.

Rhys (12:57):

Yeah. We are very messed up in that regard.

Chase (13:02):

It's very interesting to think about not just the challenges that you're helping solve, but also the opportunities presented by remote work. And I know you guys see your CEO's story is very interesting. I know a bit about your personal story because we're friends from past conversations. But when you look at your customers, when you talk to the people you guys are serving, what kind of opportunities are you seeing? Again, the quote unquote, future of work to keep using that term? What are you guys seeing presented to these people and how is it changing the opportunities that are presented to the world?

Rhys (13:44):

So, if we started digging a bit deeper into what I was saying about the employees... so our ethos is that talented people are spread around the world. Unfortunately, access to high quality jobs is not right. The current day and age, that is not something that is readily available. And of course that's what we want to change. It's a sad fact if you live in a handful of places around the world, you get access to high quality, high-paying, high-growth jobs.

Rhys (14:13):

Basically,` anywhere else in the world is incredibly focused on a handful of places. So we don't think that's fair, right. We think just depending on where you're born shouldn't dictate that. And we also think for companies as well, that there is a huge demand for talent particularly in our sweet spot, or is there a sweet spot right now in tech. And tech companies to the point that a very large number of roles go unfilled.

Rhys (14:42):

So, we see it every day. It's companies can get access to talented people elsewhere in the world. And it's a massive benefit for them. Like it's very exciting to see our customers. It's a funny thing. So there's a lot of mindset change and on the employee side and on the employer side, but specifically on the employer side, it's very exciting to see that moment where a company goes, "Okay, well, the guard rails have just come off. Shall we take a look at Brazil?"

Rhys (15:19):

You know, having that mindset shift and going well, Brazil is a pretty big country. We are a US company. So it's a pretty good time and maybe we don't need to go look at it in Japan immediately because we're maybe not ready for that, but let's take a look at Brazil. And then they go there and they find out that there's 20,000 node JS developers they can hire. And they're absolutely doing backflips because they're so excited. So for that meant, that mind shifts that change. And then for that to proliferate, that's what we're aiming for.

Chase (15:52):

It's amazing. I love that. I've heard people say before, "We don't actually even need to hire from anywhere." Like at Doist, for instance, we do hire from... We'll hire somebody from anywhere. We don't put like locations on our job descriptions. But when you see criticisms of places where they're like, "Oh, it is only within one time zone or something," you think like, look how far we've come. It used to be like only within my postal code or zip code only within 20 miles or 20 kilometers or something. And now we're talking about entire time zones, continents, and the whole world. So it has moved very rapidly, very quickly.

Rhys (16:34):

Can I just mention one thing on that point? So yeah, as much as we are obviously evangelists for remote work and things like I do, I do agree that companies shouldn't just go like hell for leather and, and try and find someone if you're an American company, hire someone in Indonesia when you have no process or no capacity to make that work, like work up to that.

Rhys (16:55):

But yes, the other thing is probably right, is that north-south alignment of jobs has not really been very common, right? I mean, you can go into the history of agricultural economies and everything, why there's an east-west because of climate zones and things, but that's how it's been. And I think that has a hangover in our mentality that you have to look east and west, but you could look north or south. So, you might not necessarily even need to go more than one time zone away because there might be millions of people north and south of you that are highly talented that you can work with.

Chase (17:33):

Absolutely. Yeah. And I do think that's overlooked for some reason or another. I 100% think you're correct. We tend to go east and west and believe that's where the talent lies if we're going to go remote. And we don't necessarily have to go that way. I also think we don't have to flip the switch from one to the other. You don't have to go from all offices to all remote and try to just nail that completely.

Chase (17:56):

You can take steps towards that and it doesn't necessarily have to be all or nothing. I think one of the underlying principles that we both talk about a lot is adopting asynchronous communication practices. And that can be one of those first steps. If you're going to hire somebody in Indonesia, all of a sudden, then you should probably have some form of asynchronous communication practices in place already. And if you haven't worked up to that, then let's maybe start with something a little closer to home.

Chase (18:30):

This has been a really nice, quick overview of Oyster. What you guys do, the problems you're trying to solve. The marketplace that you work in and that's what we wanted to get out to our customers. So thank you for providing the background and a little bit more about what you're doing personally and what the company is doing on a more macro level.

Chase (18:49):

I wonder if we can close really quickly with just a bit of advice. What kind of advice are you giving to the prototypical customer that comes to you that is drilling in deep on HR, hiring, bringing people on, need People Ops can be the broader term, but bringing people on board, hiring in different countries. What is the underlying advice that you're giving to customers on a regular basis?

Rhys (19:22):

I guess it does follow on from some of the points you just mentioned. The world has moved incredibly fast over the last two years, year and a half. It doesn't need to continue like that and the way that you run your business. There's been a lot of reacting to the world over the last year and a half. So opportunities have arisen from that and you should take advantage of those.

Rhys (19:43):

But you should also do it in a considered way. So we do tell our customers, "Look, if you're thinking about talent acquisition and hiring elsewhere, start small, start in the... without an acquisition start small." And then I think the other thing as well is also as I said, the operational capacity and internally to allow that to succeed, you probably want to pick your battles and where you roll out through the company, right?

Rhys (20:15):

It doesn't need to be a whole company shift in terms of how you do that. Maybe you want to roll over some of these ways of doing things in a particular team. First incubated there, and then spread. But that maybe the team that you're planning on growing fastest, because then, you have that compounding effect of the new blood coming into the company that is doing things in this way. Or even just in the teams that are most excited about this. There might be certain people that are particularly on board and particularly interested in making this work.

Chase (20:50):

Perfect. Awesome way to wrap this up. Thank you, Rhys. Tell us real quick, where can people learn more about Oyster and any other last thoughts that you have, but this was perfect. Thank you so much.

Rhys (21:03):

No problem. Yeah. So you can find us on all the standard social media accounts or our LinkedIn Oyster HR as well as Twitter. And then our website is www.oysterhr.com.

Chase (21:15):

Perfect. We will link to that as well, obviously in the article. Thanks a lot. Rhys. Take care. We'll see you soon.

Rhys (21:21):

Thank you.