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People and Teams
15 minute read

How to Build a Strong Remote Work Culture: An Interview with Christy Schumann

Christy Schumann, Toptal’s VP of Talent Operations, discusses what it is like to lead a 100-strong fully remote and distributed team that is responsible for matching Fortune 500 companies and well-funded startups with some of the best talent in the world.

Christy Schumann is Toptal’s VP of Talent Operations responsible for matching some of the world’s greatest freelancers with companies who need their skills. She spent more than a decade in management and consulting at Bain & Company, before joining Rackspace as a general manager of its security business. Schumann earned her BSc in Computer Science and Electrical Engineering from MIT, as well as an MBA from Columbia Business School.

In an episode of The Talent Economy Podcast, she discusses her shift from an office environment to a fully distributed and remote company—and what it is like to lead a more than 100-strong team of colleagues working to match Fortune 500 companies, or well-funded startups, with some of the best talent in the world.

Christy Schummann, VP of Talent Operations, Toptal

The interview was conducted by Paul Estes, editor-in-chief at and host of The Talent Economy Podcast.

In your history, you worked at Bain and Rackspace. I imagine that those jobs were location-based, and now you’re working for a fully distributed company. Take me through how you worked and how it changed.

When I started up at Bain, we were very location-based. Probably to the extreme. Like most consulting firms, they have a four-day client set requirement. And so, not only was I in an office but I was traveling to someone else’s office, which either required a plane or, in many cases, a one- to three-hour drive each way. I did that for a number of years. I actually spent the last two-and-a-half years or so at Bain in an internal role called the practice area, where I was able to be remote. And it was life-changing.

We had a full team I met with probably once a year. And it was really the first time I was able to see how productive a remote environment can be. It was the same Bain team and the same smart Bain people—and the frameworks and the slide decks and the Excel models. I was just doing it in the comfort of my own home.

As I continued my journey, I actually left that remote role. I got an itch and the grass is greener. I wanted to kind of explore outside of Bain for the first time. So I went to Rackspace, where I was in the office from probably eight to five, eight to six, every day. It was different. There were tradeoffs. It showed me that there were a lot of things I missed about the office: your coffee chats, your in-person meetings, where you can really get the body language you can feel—there’s probably nothing like it.

So there are definitely tradeoffs in terms of working remote. But after returning back, I can probably honestly say that I don’t know if I can go back to a full-time office environment ever again. In my own personal life, I’m actually much more productive when I am working from home. The chatter of the office—there’s benefits to having impromptu conversations, tapping on the shoulder with your teams, with your boss, with other people outside your function—but I think, in general, there’s a certain percentage of those that are not as productive as they could be. You have an impromptu chat over coffee, no one writes anything down, and you go on your merry way.

In the remote environment, we don’t have that. Every meeting has a purpose. Every meeting has an agenda that is documented. There’s usually an initiative deck circulated across a number of people across a number of time zones. So, I think the remote productivity aspect of it… it’s kind of a stark contrast from what you find in the office. And it’s something that I’ve really come to appreciate.

You brought up a really interesting point that I’ve noticed in my transition to working fully remote, which is writing things down. It’s not only writing things down, it’s the tools and the way you communicate. I imagine that, in some of your previous roles, there were a lot of emails, a lot of meetings, and a lot of PowerPoints. What tools does your team at Toptal use to do real-time communication?

Interestingly enough, we do have a number of in-person meetings. What we probably do follow is, before that in-person meeting, it is everyone’s responsibility to look at the documentation ahead of time. So, it is up to the initiative team or whoever is hosting the meeting to have some form of documentation. Even if it is a few bullet points on an agenda they are going to tick through. Here are my thoughts. Here are the open questions that we have for discussion. And so I think people come to meetings more prepared. It is a little bit easier in the office when you just get together and say, “Hey, let me throw up some bullets on the whiteboard on the fly.”

We use Zoom for all video conferencing. Slack and Google Docs—those are probably where we house most of our documentation. Moreover, Slack is literally where all the knowledge exists and the single source of truth. You don’t really have to interpret what someone is saying. When you leave a meeting, you can always go back and refer to exactly what was said or what is going to be covered in a meeting.

Colleagues meeting to discuss work issues

You have a large team, you’re operating very complex workstreams. How do you track productivity and measure success? I go back to my old days in large corporate America, and we’d sit in a room and the executive would sit at the head of the table with a big PowerPoint slide with red, yellow, green. How are you making sure that everyone’s being productive and the key initiatives are tracking?

Maybe it’s because I come from a consulting background, but I’m still a fan of red, yellow, green. Just because you are remote doesn’t mean that you don’t have decks with red, yellow, and green—and a Program Management Office that is tracking your key initiatives and the health of your business. In the remote environment and at Toptal specifically, we rely more on data and dashboards. So, not necessarily translating them always into a PowerPoint deck, although we do that still. But having the live dashboards that are dynamic at any given time allows you to determine the overall health of your business, like revenue, cost, volume, or other performance metrics at the company or function level. Additionally, we use them to diagnose operational issues—anything in an operational function that has a number of flags that go off if something is operationally going haywire. Lastly, I think metrics are critical for performance, managing your teams and individuals in a remote environment.

I’d like to make sure that everyone in our organization and talent operations knows what a good day looks like, what success is defined in terms of both qualitative and quantitative performance measures. That’s really how you get everyone aligned with the direction across countries, time zones—not having to speak to them multiple times a day.

Toptal has been a fully remote company for a decade. What have you learned, and what makes it special or different from other remote companies?

Toptal is 100% distributed. It’s the first time that I’ve been in a fully distributed remote model. When I talked about my time at my consulting firm where I was remote, I was one of a few people that were remote, and everyone else was in the office.

Having everyone remote puts everyone on a level playing field. When you have some people who are remote but most people in the office, the most important things are discussed when you hang up the call. You go through the entire agenda. Everyone says, “Okay, nice to talk to you.” And then, all of a sudden, the next steps and the actions are made on the walk back to your desks, or the walk to the coffee shop after the meeting is over. So that was frustrating. I think, when sometimes I did have to be remote when I was in an office, I wasn’t really sure if I was gathering all the context. So, Toptal doesn’t have that. Everyone’s on an even playing field.

The second thing is diversity. We are 100% remote and spread across 100 different countries. It’s been proved by many that greater diversity leads to more effective and more successful businesses. And being 100% remote, we truly do make that effort in our recruiting to post in multiple cities and countries across the entire globe, so we can get the best talent for the role.

The third is a secret sauce that’s really hard to describe. It’s just such a strong culture. Since I’ve been here, I don’t think I’ve encountered anyone who is not driven or not ambitious or not helpful. Everyone is all of those things. And I think that comes from a very strong recruiting process, which actually even includes a culture interview that focuses specifically on the tenets that we have on Toptal’s culture page. These make the candidates get asked these questions: “Hey, are you ready for this? Are you ready to be remote? Are you self-motivated? Do you rely on your office for your social life? Because if you do, this kind of 100% distributed model might not be for you.”

So I think having a very strong hiring process, a very clear vision of what a good cultural fit looks like is something that drives Toptal. And it’s impressive that we have been able to scale as fast and as large as we are with such a strong, consistent culture globally.

What advice would you provide to other executives and managers who are trying to figure out how to run their teams as efficiently and as successfully as possible right now?

I think what many organizations are afraid of is that everything they know in the office doesn’t work in the remote environment. And the only thing I think I’ve really honed in on over the past few months, half a year or so, being at Toptal—being 100% remote—is many of the best practices that you should be practicing in the office apply when you’re remote. Organizational structures don’t have to change. They may appear flatter, because anyone and everyone communicates on Slack, but that doesn’t have to change.

You should, in the office, be managing team metrics. Your teams and team members, frontline— up, down, and across—should know what a good day looks like. They should have performance metrics and KPIs. All those things emphasized in a remote environment are really best practices that you should have in the office anyway. So, I would say, don’t be nervous. A lot of the things you know already apply. It just so happens that you’re talking over Zoom instead of being together in the same room.

For organizations, my greatest piece of advice would be to not be nervous. This whole remote working, the rise of the talent economy—it’s no longer the future of work, it is now. It is now more than ever, given the global current events that are happening today with COVID-19 and the sudden rise of remote. But don’t be nervous.

I got lazy operationally, at times, when I was on location-based work. Because you could go into a meeting and draw on a whiteboard, and you didn’t have to write things down. Here, you don’t really have a choice because there’s no whiteboard and there is no hallway conversation. And I think you said it a couple of times that writing things down and having that trail is important so that more people can engage in that information and drive that consistency around the direction and the goals.

The other big piece of advice, I think, is trust. Trust your teams, trust your employees. Don’t be nervous about your talents not working. Because if they’re not doing the work, whether they’re in the office or out of the office, you’ll know. I think one of the biggest transitions is valuing results and not valuing facetime. When you see someone at their desk from eight to five, you think they’re working that whole time and you think that they’re being 100% productive while they’re in the office. I think that’s probably wishful thinking.

You have to trust your employees and make sure that you have milestones, deadlines, metrics, so that you’ll know if someone’s not performing. Which you would, in theory, do in the office as well. So you’ll be able to help the underperformers improve and help develop performance improvement plans if necessary—if someone or a team is not performing.

The last thing I would say to organizations is—embrace the ability to now have a global talent pool. Companies are being asked and forced to go remote at this point in time, which probably seems scary because it’s uncharted territory. It’s actually an opportunity in terms of them being able to expand beyond the talent pool that exists 25-30 miles from their headquarters.

So I would just take this—as awful as coronavirus is right now and the impact it’s having globally—I would take this as an opportunity to expand your talent pool and really think about how your model can be completely revamped going forward in the future.

Christy Schummann, VP of Talent Operations, Toptal

Let’s talk a little bit about your role as the VP of Global Talent Operations. I can begin to imagine how complex it must be to manage talent with clients over 100 countries, 24-7. Tell me what a day or a week looks like for the VP of Talent Operations.

A little bit about talent operations, because I think it might be a misnomer. A lot of people think that we are recruiting talent. But Toptal’s entire business model is sourcing, screening, and then matching freelance talents with clients, based on their needs. And that is talent operations. This is the team that really creates our network of thousands of people that are ready and willing and able to help clients on a remote basis, largely based on their needs from across the world.

So there’s an entire operation of people—over 100 people—that’s supporting this expert pairing to ensure that the client and talent both get what they want. It is complex because in many businesses, you have one end customer and you have a product or a widget or a piece of software that you’re selling. In this case, it’s unique because we have a two-sided marketplace where, on one hand, you have a number of global, well-funded startups or Fortune 500s. Then, on the other side, you have the most highly skilled talent in the world.

And you have to figure out how to make both sides happy. So, we have two customers—the client organization in need of talent, and then the talent, the freelancer. It’s important that we deliver both of them a very client-centric experience where they feel like they’re getting the value that they sought out in the first place when coming to Toptal.

A lot of people think of the talent economy and the various platforms like there’s just an algorithm that takes care of the matching. Help me understand how the operations process works.

Our process is fairly complex because we’re dealing with clients who have certain needs, and talents who have certain needs. You have to have this expert pairing. We believe it requires a really special human-curated process. So we’re not HR. We have an entire operation that is dedicated to sourcing the talent, screening and vetting the talent. That takes away all that need in terms of “Let me narrow it down to the final five. Now, the final three. Now, we do an assessment.” We’ve done all that already for the clients and the talents, for that matter. We get to know the talents during that process as well, what they’re looking for, what their skills are. And when it comes down to placing talent in real time on demand, we can do that very quickly because it requires a certain level of complexity that algorithms can’t deal with. We have humans helping to make that expert pairing. And we’ve also done a lot of upfront work and research so that we are able to have a match in a less than a 24-hour window.

A lot of the Fortune 500 companies are location-based. How do you bridge that last mile connection?

For us, I think it really depends on the client. We have a number of these startups, smaller companies, or even mid-size, mid-tier companies. And we find oftentimes that our customers actually appreciate the fully remote model. And for us, it’s like eating our own dog food. If we’re promoting a network of remote talent that can work effectively for you three time zones away, then we should be able to work with you remotely as well. Still be able to maintain that same level of client experience and responsiveness as we would if we were onsite, embedded into your recruiting team, for example.

That being said, we do have a number of enterprise clients, as you alluded to, where face-to-face interactions and relationships are still very important. We’re all still human. We want you to trust your partners. Therefore, we do make those in-person trips in certain situations. I would say our client model is not really one-size-fits-all.

Brainstorming session during an offsite

One of the things that’s interesting is people start embracing remote. As an executive leader, how do you help teams and people who might be new to remote?

It’s a really great question—the topic of work-life balance in a remote environment. And I have a number of friends who look at me in a completely remote environment and say, “Oh, you must be working 20-30 hours a week because you’re working from home. You get to have lunch, and do your laundry, and go grocery shopping during the day.”

As a remote worker? I wish that was the case. I found myself working more hours.

It’s exactly right. The perception is completely false. I think for many, it’s actually harder to create boundaries when you’re working from home because your home is now your workplace. There are no boundaries, like your phone—I mean, we’re all attached to our phones. Slack notifications are going off during the day, even when I am in the kitchen making my tea for the three minutes I’ve stepped away from my desk and my headset. So, I think that’s a very false perception. We actually work a lot, though I think our leadership team works a lot to make sure that we are promoting the flexibility of what Toptal is all about.

I am a pretty open book with my team. I like to think that I lead by example. I make sure that I take advantage of the flexibility in terms of not missing those special events with my family, like the Halloween parade or school performances. And when I’m going to those, I’ll let people know “Hey, I’m offline from two to five. I’ll be back on after the kids go to bed.” And I’m always online at night, but it allows me that special time from probably 5:30 or 6:00 until 9:00 to have uninterrupted time with my family.

It’s just a matter of transparency and letting people know when I have to dial off, when I can be available later. And I think leading by example—and just showing people that I am able to get things done while also maintaining this sense of flexibility—is at least something to show them that they should be doing the same thing. Because it’s really up to each individual to be proactive about how they set boundaries.

A lot of times, I’ll work Saturday and Sunday in the morning, but that’s because I couldn’t do anything Friday after 3:00 PM because I had to pick up my kid from school for his swim team. It’s not about facetime or when your Slack bubble is green—it’s about your results and your output. With a globally distributed team, with everyone working across multiple time zones, no one really asks what you’re doing, where you are.

Many of us are available I think during the core business hours. But if there are a few times when you’re not, no one is alarmist about it. Whereas, if you didn’t show up to the office on a Thursday after lunch, people would start asking, “Where are you?”

It’s important, like you brought up, for people to think about flexibility. If we were to look 18 months out from now, to the way work has changed for large companies and mid-tier companies, what do you think are some of the things out of this experience that represent durable change?

I think this is a monumental, unprecedented shift for the global workforce. If I had to look 18 months down the road, I think most companies will offer some sort of remote program. I do think that many companies will go back to the old ways of working. They all have offices. They all have real estate investments there. And it’s not just going to be an empty office. But I do think that they’ll have their eyes open to some sort of remote program. And as they figure out how to retain employees, much of that will be around remote and flexibility. I have to move, maybe for a personal issue or for my family or for my spouse. Allowing your employees to go remote, I think, would increase your retention. Why do you want to lose that talent only due to location? That doesn’t seem to make a lot of sense, given that all of the tools and technologies are now available to companies, big and small, to allow for a productive remote environment.

The second thing I’d add if I look 18 months down the road—the talent side will be freer and they will be looking for more flexibility. They will get used to this sudden rise of remote and say, “Hey, I like this. I like this flexibility. I don’t want to go back into the office for 10-12 hours a day away from my family.” I think the talents and the teams will start to realize that flexibility is indeed attainable. Maybe you don’t go into the office five days a week. Maybe you go in two to three days a week and you have a handful of days that are remote. I think it will just change the model for many companies.

Understanding the basics

There are many companies in the world that allow remote work or are fully remote. Some of the more well-known names include Toptal, GitHub, InVision, Hotjar.

To work remotely means that you can work from your home or a shared space with only a laptop and internet connection. It means that you do not have to commute to a particular place every day to perform your duties.

The disadvantages of remote work are related to your social life. Working remotely alone can be a very isolating experience, and thus, every remote worker needs to have a plan how to maintain a healthy social life.

Culture in the workplace is a set of shared norms that all employees subscribe to during work time. Workplace culture creates a sense of community in which everyone is working toward the same goal.

Benefits of remote work include time saved on commutes, flexibility of working hours, and fewer office distractions.