SafetyWing CEO Sondre Rasch joins the show to talk about the challenges of offering benefits to contractors around the world and to discuss his philosophies on remote work leadership.

Remote Talks: Episode 13 with Sondre Rasch - Freelancers, Nomads, and Benefits

Remote Talks

Remote Talks is a series of video interviews with the brightest minds in remote work and global employment, hosted by Remote CEO Job van der Voort. This week features Sondre Rasch, CEO of SafetyWing and an expert on all things global contractors, insurance, and remote work.

To see the full interview, watch the video on this page or view the Remote Talks playlist on YouTube.

And don't forget to subscribe to the Remote Talks podcast!

Sondre: SafetyWing is building a global social safety net for remote workers and teams. We are for today in health insurance for nomads and also remote teams and workers worldwide. 

Before this, I ran a platform called SuperSide. Today, it's still active, and we wanted to provide benefits for the freelancers on the platform, but we needed to do it in a way that was worldwide because they were spread out worldwide and nobody offered it the way we needed to buy it, which was global. But also we needed to make it easier to buy, ideally an API and flexible to turn on and off. That was sort of the problem discovery moment, and because I had previously worked with the Norwegian social safety net.

After trying for a year to get someone else to start this company with, I said, OK, someone has to build this. There's this infrastructure that needs to be built for remote work, and the social safety net is a big piece. That was the genesis for the company. 

Why do you think no one had tackled this problem of benefits for global freelancers before?

Sondre: It is surprisingly difficult. Every company has their complexity. This one is it's the legal barrier to entry, roughly. And the financial barrier to entry as well. So just to get the product to market, you need to figure out licenses on multiple levels in all countries, to make a product that is simple.You also need the backing of an insurance company. And those kind of prove a big barrier to entry, because if you have a vision that is different from what existed before, you have to persuade these very conservative actors to go along with it. This is why we see so few startups in this area. 

Are insurance services through SafetyWing for nomads or all remote workers?

Sondre: The person we work with is the remote worker, I think, the best description of it. Nomads is more a subset of remote workers.

If you think about it in the product adoption life cycle, I myself lived a bit nomadic in the sense of working remotely and living abroad. We started with that group, partly because we knew it well, but partly because as an early adopter, a lot of things nomads do today, everyone else does. A few years later, and we've seen that across multiple product categories, so it's a place to start. However, the user we have in mind in the long run is that most companies will be remote, and everyone who works will be part of an international workforce that has to have this global infrastructure to support. And that's what we're going to provide. The social safety net part.

Are there any areas of the world where you’re seeing particularly strong remote work expansion?

Sondre: Yes. We are seeing some countries that were early in vaccination grow. People I believe are eager to get out, and that's one area of growth we see. As for remote teams and remote workers, that's a pretty broad based growth where you see it. For us across countries and fairly spread out, we haven't been able to discern any particular patterns yet, with the exception that, of course, we see some of those countries that have a lot of people working only remotely, like the Philippines, being a bit ahead of the curve on their end. But this is a worldwide phenomenon. 

What happens when a citizen of one country moves to another, from an insurance perspective?

Sondre: So if you're in the US, even moving to another state would require you to undergo everything from the ground up, because all the infrastructure and the insurance are only legal in one state. And so it is between countries. Typically, we have built our policy from the bottom up to be global, so it's not an issue for us.

One of the benefits we can offer that's a regular kind of national insurance provider is that if you move or if you're abroad for a place of time, you have the same coverage as you do at home. You see some companies like Spotify. When they went remote, they said work from anywhere, and they're working to kind of set up the rest of their company to function in that way as well.

That is a big perk. As people work remotely, they are more mobile. If you work abroad, moving home to your family for parts of the year or to a summery place part of the year, that is now much more possible. 

Learn more: Create your customized list from the best destinations for remote work

What kind of challenges do you experience with local governments?

Sondre: We both are in that area where we are deeply regulated in places and we want to make a simple product that works globally. So we have to deal with the differences between countries and, like you said, in insurance, it is also somewhat invented locally. There are differences between countries. There are some instances where you have to have it in one jurisdiction, like the EU, and then it's illegal in another, like the US, and that's sort of the edge case there.

We look for things that are legal across categories so that we can make something that is legal everywhere and that is broadly successful. It is possible, but it is part of our product development process, essentially. 

Job: What is this one thing that is illegal in the US, but mandatory in the EU? Just very curious. 

How distributed is your own team at SafetyWing right now?

Sondre: We have over 50 on the full team, sort of 80 in total across 60 countries. So we're an extremely international team. It works out really well because, of course, a lot of the people grew up on the internet, and so there is this shared cultural reference that comes from that. But it is more important for our company to have a worthwhile mission and values. Because people have different contexts that they come from. But it is going really well.

We have a remarkable team. It is a lovely benefit to be able to hire from anywhere is that you can find these really rare people to work on your team.

Sondre: Yes, so we would do team gatherings three to four times a year, with a break during COVID. We do have plans to resume in the autumn. Conditional, of course, of that being safe at the time. These things are a bit hard to predict, but that is a key part.

We do those for one week, and we have a great setup. It's not just team building activities. We try to put a lot of stuff that is the long-term planning in those weeks, and it's been a great way for us to work remotely.

What’s your philosophy on providing benefits to people in multiple countries?

Sondre: I'm pretty sure shortly it will be that you are expected to have the same benefits for someone you hire locally as internationally. We're in this odd situation where even among big companies, they think that they can have a completely different set of norms and rules and benefits for international employees. But that is definitely in the middle of shifting. That's roughly how I think about it. I do think that some benefits have to be reimagined. Some are a lot more useful when you do it internationally, and some are a lot less useful when you do.

Obviously, anything that is in the office becomes completely useless and has to be replaced, like things like office stipends. When it comes to big benefits like health and retirement, the issue is usually the international part. Are you able to offer the same worldwide?

Before you had services like Remote, almost everyone, even the most serious employees, would go with a contractor model. Part of that was because it's so difficult to do anything else. But now, with Remote’s service being started, it's starting to make that easier. And for serious employers at least to have a realistic option that isn't an impossible barrier of difficulty. 

Learn more: Onboard your first global employee in minutes with Remote!

What has surprised you the most about the global insurance world?

Sondre: So many insurance policies are hard to read, and it has good reasons because, especially in common law countries, you have these phrases which have documented precedent, and the insurance policy is a collection of those. But the underlying thing it's trying to say is often very simple, and it could almost be said to be programmatic. Like there are events and then there are conditions and then there are limits. But you're finding yourself living in this history.

I also find that the entire insurance industry is one of the least digitized. It is changing, but there are significant parts of the insurance industry, both in the sort of distribution and product side which exist almost like the free software era, not just pre-internet, but like pre pre-digital. I wouldn't have guessed that. So that was a surprise to me. I would have guessed that it was behind, but not that it was the degree that it is. This explains a lot about what is odd about the insurance industry. It is just a very deep and broad need for renewal and becoming digital. But it's a very conservative industry, and they're very bound in rules and regulations, which has made it sort of a bit of a laggard. So a lot is going to change in the decade ahead. 

Learn more about SafetyWing and Sondre at SafetyWing.com.

SafetyWing CEO Sondre Rasch joins Remote Talks to discuss the challenges of offering benefits to contractors around the world and to discuss his philosophies on remote work leadership.

Remote Talks: Episode 12 with Ellen Pao and McKensie Mack - Creating People-First Remote Workplaces

Remote Talks is a series of video interviews with the brightest minds in remote work and global employment, hosted by Remote CEO Job van der Voort. This week features two very special guests: Ellen Pao, CEO of Project Include and former CEO of Reddit, and McKensie Mack, anti-oppression consultant and founder of MMG, a social justice organization based in Chicago.

You recently co-authored a report on harassment and mental health in remote work. What did you learn?

Job: Regular listeners know that I care very much about the intersection of diversity, inclusion, and remote work. Project Include, you recently published a harassment report with that alone. 

I have been reading that with great interest and a bit of shock too, to be honest. Could you give a slight overview of what were the findings of the report? What is it about? I'm also very interested in all these, beyond just interest. What gets you started on something like this?

Ellen: Project Include has always been very data-oriented. When we learned during the pandemic that there were more people who were experiencing harassment and hostility working remotely, we decided to take a data-based approach and survey remote workers, and see what we found. 

We ended up surveying almost 3,000 people. I want McKensie to dive into the results. It's been a very sobering look at what remote workplaces mean, and also the presence of all of these biases and problems that are in our offices and our physical workplaces and how they carried through to our remote workplaces. And in many cases were exacerbated.

Job: Having seen the report, what was your response on a high-level overview, high-level thoughts?

McKensie: We talked about a lot as a research team the fact that 85% of workers have been experiencing increased anxiety since COVID-19. That's so important to name at the outset because it speaks to the ways in which all of us are impacted by the global pandemic and the ways in which oftentimes we think of work as being separate from our personal life.

We think of the emotional impacts, the intellectual impacts, the mental impacts of the pandemic being something that we experienced most at home. But the reality is that, of course, that impact is going to follow us at the workplace. And not only is it going to follow us as individuals, but it's had a major impact, for example, on the way that black and brown folks, Asian folks, other people of color, women and non-binary people, folks with disabilities, are being treated within these remote workplaces.

Black, non-binary people, and women are nearly three times as likely as non-binary people and women in general, to experience race-based hostility. Trans people are nearly twice as likely to have experienced increased gender-based harassment since COVID-19. Ninety-eight percent of those folks who experienced increased gender-based harassment were women or non-binary folks.

See also: 8 experts discuss mental health tips for remote teams

When we think about just some of these numbers, because that's not an exhaustive listing of our findings, but what we know from those findings is that the ways in which folks are experiencing harm and harassment in the remote workplace is increasing. Versus what I think some folks might think would be the opposite in that you're not in the office, you're not in a physical space with folks. So maybe there is not as much contact with people. The opposite is true in that. Folks going into these remote workplaces are now experiencing even more harm than previously.

Where should companies be more vigilant about harassment in remote work?

Job: It's honestly shocking to read for me. The numbers are chilling in and of itself. I know it's a stretch, but do you have a personal goal theory? Do you have thoughts on, why is it an accessory of remote work? What is it that changed other than the absence of the office?

McKensie: First I'll start with something that's not a personal theory. These are systemic problems, right? And systemic inequities that existed long before the pandemic. That's not a personal theory. That's an actionable and tangible reality, especially within tech.

We think of systemic inequity as being like water in a pot. And then you add the stress of a global pandemic, where there are a lot of folks that are feeling powerless, as if they don't have control of their environment, because they really are not in control. The pandemic could be, in this analogy, considered sort of like the fire. 

So you have the water that's already been there. And then you add the heat of increased anxiety across the board for folks, regardless of their gender identity, sexuality, race. What eventually happens is you get an uptick in harm, because then those folks who hold the most privilege and power within companies are feeling that sense of anxiety and also feeling a lot of concern for the future of their companies, and potentially then exacerbate those issues, harassment, because now they're creating an environment that's even more controlling and domineering.

One example I heard: there was a remote company where folks were actually required to check in with their managers remotely, at least three to four times a day. Why would you need to check in with your manager that many times in an eight hour period? Of course, that's going to really raise a person's sense of anxiety within the workplace. That's also going to increase the likelihood that somebody is going to be harmed, especially if it's that much control being pushed onto workers in that environment.

We’re strongly against monitoring remote employees. How can remote managers do better without these invasive tools?

Job: One thing that we see in a lot of examples is that employers start to monitor their employees with software that actively monitors employees. You see all sorts of trends on the internet, “I have to make sure my mouse keeps moving,” so that they give a false sense of presence at work. I always find that somewhat of a scary prospect that would be very uncomfortable, working in an environment where someone feels the need to constantly check on me and to look at what I'm doing.

Ellen: A big part of it is also that people aren't great managers sometimes, right? If I don't trust my workers and I don't know how to manage them, then I'm going to use these surveillance tools or I'm going to use these check-ins because I'm not confident that they're actually doing the work that I'm asking them to do. 

I might have too many Zoom meetings or phone calls, or I might have the keystroke checks or the mouse checks, or there are some companies that are using software that keeps the video on and that's watching you work all day. All of these aspects are tied to this problem: that there is a lack of trust between the employees and the companies and the managers.

Part of the reason why we're seeing increased harassment and hostility in all forms, gender-based, race-based, sexual orientation-based, it's because employees don't trust their companies to deal with these problems. So they don't report, they don't bring them up, they don't try to resolve them. And then, the person who's perpetuating the harm continues, and other people might be observing that it's okay and it's allowed.

Sometimes we had survey responses say it was like their head of HR or it was their CEO who had the inappropriate comments or the inappropriate behavior. That just fostered a culture where the harm-doers felt comfortable doing harm, and the people who are experiencing the harm did not feel comfortable reporting it. That's a big problem.

In this pandemic timeframe, we also saw huge protests against systemic racism. We saw a lot of racism in the counter protests. We saw racism against Asians coming from the then-president of the United States. We saw all sorts of issues people were struggling to deal with which caused anxiety to the people from the groups being discriminated against. It was also a threat to the people who have enjoyed these privileges and who feel entitled. All of a sudden they're facing people calling for change, and that change is uncomfortable.

In order to restore the control that they want, that McKensie brought up, they may be more hostile. There may be more harassing. We're fostering this environment where they're allowed to do that. They're also feeling this work pressure and anxiety from all of these additional factors.

Many organizations falsely believe they don’t have these kinds of problems. What should leaders be doing more of?

Job: Many people will be listening to this and they'll be thinking, “Well, that's other organizations. That's not happening in my organization.” One of the things that the report found was that leadership is often not aware of problems existing in their organization, or maybe getting worse through word of mouth through the pandemic. What are some of the things leadership can do? The people that are listening right now who think to themselves, “Well, I'm not aware of these kinds of problems.”

McKensie: I love this question. Thank you so much for asking it. I think it's in alignment with something that Ellen just shared, where she talked about how there are folks who don't trust their companies to actually do something about harm and harassment in the workplace. 

In addition to that comment, I would add that also there are a number of leadership teams within tech who don't trust their workers to actually tell the truth about what the culture is like. Who are like, “If you're coming to me with something critical or negative, it must be because something is wrong with your perception, or you just can't cut it in this environment.” One of the first beginning pieces around that is, are leaders actually developing processes where workers can speak honestly about their lived experiences?

One example of that is through an equity audit, where it's a mixed-methods research process that's held and implemented by an external partner that includes both qualitative and quantitative analysis of what's happening within an organization. That within that qualitative piece offers workers confidentiality, so that they can actually share honestly about their experiences and really talk about the ways in which they are experiencing the culture. Which can happen where they experience not just harassment, but it can also happen where they're sharing experiences around operations and the ways in which, potentially, situations from colleague to colleague that start off as conflict...but because there are no systems and no education as to how to deal with conflict, they can easily become harm and harassment. If left unattended to. It's really about providing those resources, but then also creating some sort of a data-informed strategy for how culture can be evaluated over time.

Job: The idea being that if you start to implement changes, you test again, you measure again, and you see how the organization progresses. Exactly.

Can training, such as bystander training, help reduce these problems for remote teams?

McKensie: What's happening right now in remote working environments, within tech specifically, is there are a lot of leaders who might hear a complaint of harassment and the response is, “Okay, give them bystander training.”

There's nothing inherently bad about bystander training. Bystander training is really good. We're talking about identifying harm, stopping harm, intervening. At the same time...we're providing these resources and tools, but what actually is the state of harm in our organization? What's the state of repair in our organization, our company? In addition to that, what kinds of systems have we put into place so that people can anonymously report their experiences, and then what happens to those reports? 

It's not enough just to provide the space, but then are we actually listening to what people are sharing? Are we actually evaluating that? If we have established it, is it something that actually informs our company strategy in the long term?

Ellen: Part of it is solving the root problem, which is does your company actually value inclusion? Does it actually want people to be treated equitably and to ensure that that's happening? A lot of times you do need training. We have a set of company values that includes these concepts of fairness and equity. We have a set of expectations, whether it's in a code of conduct or in the processes that you run, that incorporate these ideas of fairness and equity and justice.

If there are people who don't understand it, maybe they need to go to training. Maybe they need to understand the history of our country, the history of our systems, and understand this is what we're fighting against and that we need to make sure we're not incorporating into our companies. 

For a lot of companies that means training your leadership, training your CEO, and training your board. It comes from the top and it works its way down. People look to the leaders for their behavior and their statements for direction. If your leaders don't understand it and aren't practicing it, it's not going to happen in the rest of the organization.

Why are companies struggling with inequity in employee benefits?

McKensie: Let's say there's a tech company. Within that company, leaders are saying, “We want to improve the ways in which our employees are experiencing the workplace. We know that there are a lot of folks that are reported experiencing burnout. We're going to provide them with access to a mental health app, a wellness app. That's going to be the way that we're going to solve the burnout issue.”

See also: The best employee benefits to attract top global talent

Again, not inherently bad, but if you're not actually getting to the root of what's creating that burnout, you're just basically putting a Band-Aid on it. So we need surgery.

Something that we recommended is thinking about the ways in which time off benefits are structured, and having a required minimum for people to take time off. Because we know that in the society that we live in, organizational trauma is very real. Even if you have a fairly decent and very welcoming time off policy where people are validated and affirmed to taking time off, depending on folks’ past experiences, they still just may or may not do it. 

Job: The vacation days are very relevant. We hear this a lot in the tech industry, where everybody gives unlimited vacation days, but the reality is if you take more vacation days, you're more likely to leave the company permanently. When we started Remote, we immediately implemented a minimum amount of days off, exactly to prevent this. I think we actually struggle to get people to the point of taking enough time off. I think it's 20 days that we have now, a little bit more than that. We'll start to see that people haven't taken their proportional amount of vacation days off, and we have to start telling them, “You have to start taking vacation days off, or you will have to take the entire month of December.” 

You should actually be taking them off. I think that is so challenging. There's a very different attitude as an employer, where I think in the past it was culturally acceptable as an employer to not. So essentially those days are like a gift to the employees. Whereas now if you're a good employer, it's your duty to do the opposite. To say look, you have to be living life and doing well in your life to be able to do a good job, and we cannot expect it to be the other way around.

How can companies be better about ensuring employees actually take enough time off?

Ellen: You have to make sure that people don't feel pressure that they're missing out on that time to do work. That when they get back to work, they're going to be overwhelmed. One reason people might not be taking their time off is because they feel like they are underwater and they will get even more underwater.

There's already all of this additional anxiety around the pandemic. People are working longer hours. They don't think the work will stop. They have the same amount of work. If I take a day off, then I have to do twice as much work that day that I come back. So giving people a sense of a lighter workload, that during those times off, you're not actually accruing more work. You're given a real day off. You have the same level of work when you return. That part is not happening for a lot of people. They don't feel confident. That day off becomes one filled with anxiety at what they're going to return to.

Job: One of the coolest things I've seen recently was a company where the out-of-office reply was, “I'm out of office. All incoming email will be deleted.” They're like, if you need something from me, I'm available again after July 15, and you will have to resend your email because the email will be deleted. 

If you really think about it, it's a reasonable thing. I think we all know exactly what you're saying. I come back to work from vacation, and I have a massive email inbox. Do I declare email bankruptcy? That is easier to do if you're hiring in an organization, but for most people that is not at all something that you might feel comfortable doing. Although I really hope that the people in our accounts payable don't apply that strategy.

What can companies do to make benefits more inclusive?

Job: So we deal with benefits in every country in the world. What we see is that statutory benefits are all over the place. In particular maternity leave. In some countries it is independent of the parent, whether it's the father or their mother or caretaker, whether it is an adoption or not. In other countries the mother gets maternity leave and the father has to return to work after three days. If you're a modern company, how should you approach this in the first place?

McKensie: Something that I would like to see more from companies is being more imaginative around the ways in which they develop benefits for their workers. I'll give an example of Patagonia in the seventies, and the idea at that time offering people parental leave was considered just so forward-moving and so progressive. 

I'm sure at that time a lot of companies considered it to be something that was completely and totally unnecessary. Now we consider it to be, not in all companies, unfortunately, but in a lot of companies, we consider it to be something that is absolutely required. Something that is a basic necessity for benefits.

It's really pushing companies to think about what it means to be as imaginative as possible. How are you actually listening to your employees, getting a better understanding of what their needs are, and then applying that to the ways in which you frame your strategy around benefits? 

A big one too is being as trans inclusive as possible. For example, there are a number of companies that when they're referring to benefits, they use terms like maternal leave. We know that there are men with babies, there are non-binary people with babies and children, and also parents who adopt children, who foster children. Those who have children in their lives and are caring for children. It's thinking expansively about the ways in which people experience life and understanding that what might've been acceptable and reasonable in the nineties or in the eighties is going to be completely different now. 

As we evolve and grow, we should become more considerate of the ways in which our companies and cultural environments are able to have an impact on our society.

Job: I think it makes total sense. From our perspective, we see this internationally playing out very differently.. We now see countries where it is parental leave in any form. It's independent of what their exact relationship is, independent of gender, it's as exactly as you would want to design these kinds of things.

We see the exact opposite as well. The classic example of the mother who gave birth is the one that gets time off, and that's it. There's no reason that the employers don't give better policies and set better standards. You don't have to follow necessarily what is statutory or what the government prescribes.

What kind of innovations can companies pursue to address these issues of benefits? Who is responsible?

Ellen: McKensie and I would love to see companies be more innovative. Instead of taking that minimal approach of, “What do I need to provide?” to start thinking out of the box, to start thinking in a more humane way in this whole movement around workers with dignity.

What do we need to provide in order to let people lead dignified lives? The one additional point, I wish people would think about how they actually implement these policies. We've heard from a lot of people that they don't feel comfortable taking some of benefits that, while the benefit has been offered, certain groups aren't allowed to take them. When they apply for the benefit or when they inform their manager that they're taking leave, they're rejected from it. Others feel like they don't have the position or the goodwill, an entitlement to take these benefits.

See also: Women in the era of remote work: What's new and what's next?

It would be great for people to track who's actually taking these benefits and using them and who is not. For your company, who are these people who aren't taking 20 days across the year, do they fall into specific categories? Do they have specific functions? Are they in specific levels? Do they have one manager?  Are there patterns that you can see where there's a problem that might be deeper than just, “I'm not taking the benefit because I forgot about it, or because I haven't been thinking about it,” but there's actually something a little bit more systemic in why they're not doing it. I wish people would look at that and think about, “How are we implementing it in a way that makes sure that everybody who's entitled to it actually takes it, because we're offering it for people to use.”

Job: One of the things that we try to do is to partially make this the responsibility of their manager. So that you, as a manager, are responsible not just for growing a team and coaching the people that report to you, but also making sure that they take time off, making use of the benefits that the employer provides.

I've experienced this myself. If you have a manager that pushes you to take time off, to say, “No, you have to take time off. It's part of my evaluation of you. Are you actually taking care of yourself? Are you actually making use of the benefits that you've had?”

I think that is the situation not many people have been in, but if you are in that situation, it's really empowering. There's not this inherent bad feeling of taking time off. “I'm making use of these company resources that have technically have been allocated to me, but in reality, I'm just taking something away without rewarding you back immediately with work.” 

How can companies help employees not feel guilty about using their benefits?

McKensie: We talked about education earlier, and I think it's recognizing that. Right before this call I was on a call with three founders of a health tech startup. One of the things that we were talking about was how when you're hiring folks, you're being very intentional and aware about your hiring strategies and recognizing the ways in which people are actually impacted by systemic inequities.

If I were looking at the demographics of an organization, based on the intersecting demographics, I probably could make a lot of assumptions about who's going to be really comfortable taking time or actually using benefits as a whole. Who is not going to be comfortable and confident doing that because of the ways in which our society has been structured around our identities.

It's important to recognize that people need not only an invitation, but the more that folks have experienced systemic inequities and the more that folks have experienced organizational trauma, the more support that they're going to need. Actually taking those benefits and taking that time, which is going to be modeling for them that the time can be taken. It's going to be modeling for them that they actually can. Let folks know that they are taking parental leave and don't have to worry about if they're going to come back to a job or not.

It's going to be modeling the fact that people can take, for example, self-care days or mental health days. That's something that they're not going to be punished for in the future. Explicitly saying that on a regular basis and including that in employee handbooks, including that in consistent and regular training. Instead of recognizing if we are actually being innovative and being as imaginative as possible around our benefits, we have to recognize that we have to create a runway for our workers so we can take them along with us. Which means providing explanations and being very clear about what our intentions are.

Ellen: McKensie's suggestions will also help with a culture shift. For many companies, these additional benefits are new, and there will be some workers who don't agree with them, or don't value them, or shun or make fun of the people who are taking them. I remember the first person that I knew who took what was called a paternity leave at the law firm that I worked at. He didn't take the full 16 weeks. He came back early because people were not kind to him. 

They said that he was shirking his duties as a lawyer. That internal behavior from your colleagues and your coworkers can be very intimidating and prevent you from taking the benefits, even if a company is saying the right thing from the leadership level. 

Job: These kinds of things flow from leadership. They set the right examples. If they simply ignore these kinds of problems, if they ignore these attitudes within the organization, then that creates a toxic environment.

What is the next big step for remote work inclusivity?

McKensie: I am going to shout out organizations like Project Include  Code 2040, the Algorithmic Justice League. I say that because I think one of the ways that we get to a future like this is a way that we get to, for example, better legislation within our society. 

It takes a lot of mobilizing and organizing of people around these issues. A lot of educating folks who potentially might be in tech, but may not be in positions where they actually wield power and authority to be able to change systems but do have power to be able to use their voice, to name the ways in which systems that are being created within these companies.

In addition to that, it takes companies being willing to make commitments that are tangible and actionable. Commitments that go beyond the diversity statement and “We support the Black Lives Matter movement. We stand in solidarity with Asian communities.”

Commitments that actually are measurable, where you could look from one year to the next, see the ways in which an action that's been taken is actually making progress or even see the ways in which it's been ineffective, which is still a very important data point. Because if we know the kinds of things that we've done in the past, we know that they haven't worked and we know why they haven't worked. It puts us in a better position to be able to create systemic solutions to systemic problems that are not focused on tools — tools are not the problem here — but that are actually focused on people and systems.

Ellen: I also think there's a change in general public perception. The new generation of workers, they want diversity and inclusion. Benefits are one way that they measure whether a company is diverse and inclusive. They are going to make the decision with their feet. They're either going to join a company or they're not going to, and that's going to put pressure on the company to incorporate better benefits, to incorporate better practices, to think about it more from the CEO level down. Because our world is changing. 

The next generation has a much different perspective because they're much better informed. They're more aware of all of these systemic problems that we grew up with. I grew up, I didn't know about any of it. I grew up thinking the world was a meritocracy, and it was a shock when I went into the workplace and I tried to process all of the things that were happening that didn't make sense. Until I finally really came to the realization, “Oh, wow, this is a systemic problem. It's not an isolated incident.”

They will also change the cultures of our companies as they become more and more of a bigger percentage of the employee base. I also know that there are a lot of CEOs who are thinking about these issues in a deep and meaningful way. A lot of them are struggling there. It's not something that they've experienced. They don't have the lived experiences and they have to learn that. People are telling, sharing their experiences. They're talking about the problems. We're seeing a lot of data coming through. The organizations at McKensie mentioned, in addition to Project Include. The data's out there, the stories are out there. We're going to see a next generation of leaders that doesn't look like the generation that we've had for the last 30 years in tech.

We're seeing more and more CEOs who are not white men. Who are more black or brown, who are Asian, who are indigenous, who are women, who are non-binary, who are transgender. It's a different world. As we see more of the people who don't share the old views, who are bringing in these new ideas, who are changing the way benefits look, we'll see many of them be successful. And we'll see them leading the way, and having other companies follow and emulate their success, because they want to be in this next generation of leaders.

McKensie Mack can be found at McKensieMack.com. Ellen Pao can be found at ProjectInclude.org. Read the full Project Include Harassment Report by Ellen, McKensie, Yang Hong, and Caroline Sinders for more information.

This week, Ellen Pao (CEO of Project Include) and McKensie Mack (CEO of MMG) join Remote CEO Job van der Voort to discuss their new report on harassment in remote workplaces and share strategies for companies to create welcoming remote environments for all.

Remote Talks is a series of video interviews with the brightest minds in remote work and global employment. This week, Remote VP of Growth Elisa Rossi hosts the show with special guest Sarah Aviram. The author of Remotivation, Sarah is a Fortune 500 HR expert as well as a passionate advocate for remote workers.

Subscribe today and never miss another episode of Remote talks. To see video episodes, you can also visit the Remote Talks playlist on YouTube.

Sarah: My career has been in HR and talent development, leadership roles at several Fortune 500 companies like Avon, PepsiCo. Some other, smaller, high-growth tech companies as well. I’ve focused on helping people find their motivation, find fulfillment in their work, and perform at their best. I’d love to share more about it.

In 2019, you lived and worked from 12 countries in 12 months. How was that experience?

Sarah: The experience was incredible. At the end of 2018, I was a director of talent development for a division of IAC. Our CEO asked me, “How do we become competitive for talent versus other companies in our space?”

Read more: The best employee benefits to attract top global talent

And one of the many trends that I looked at was remote work. This is way pre-pandemic, remote working was a growing trend, more and more individuals wanting to work remotely and more companies like Remote setting themselves up as virtual or fully distributed teams. So long story short, I pitched to him the idea of me being a guinea pig and understanding what are the challenges and opportunities that remote workers face. Perhaps I could get experience traveling the world and looking at what those opportunities and challenges are, and if it was successful or not successful, we would have some on-the-ground research to bring back to our company to figure out, is this an opportunity or perk we would offer to our employees? Which is now what is happening.

I was in one country every month. So, Lima, Peru; Santiago, Chile; Medellín, Colombia; Mexico City, Mexico. Then we went to Asia, to Hanoi, Vietnam; Kuala Lumpur, Malaysia; Chiang Mai, Thailand; Kyoto, Japan; to Europe, in Croatia; Valencia, Spain; Lisbon, Portugal; and then ended in Cape Town, South Africa. It was incredible. And I was lucky that I was traveling with a cohort of other remote professionals. We worked in co-working spaces, and I was really exposed to all different types of remote workers, both employees and organizations, as well as freelancers and small business owners.

What did you notice in terms of the optimal setup to make remote work?

Sarah: Community is really important for a lot of people, especially when you're on your own traveling remotely. So I think people feeling like, although I'm on my own, I have other people that I can brainstorm ideas with or connect with. A lot of people really enjoyed being able to work in co-working spaces in different places.

I noticed that was above anything else as a remote worker, Wi-Fi is obviously the most important thing. So anywhere that has a strong connection is ideal. We had certain instances when we were in Cape Town, South Africa, in the summer where it gets really hot and the city has to shut down power for a couple hours in different parts of the city. So we had to make sure we knew what the schedule was. We were at a place where there'd be a generator and things like that. We got lucky that we were in these great co-working spaces that helped to make sure we had Wi-Fi and that we could get our work done.

You have had a great career in HR leadership. What made you decide to start your own business and write your book?

Sarah: While I was experiencing this, working remotely from 12 different countries, I noticed something really interesting. A lot of remote workers thought that having the freedom and flexibility to work from anywhere would make them feel happier and motivated in jobs that they may not have necessarily that much. But then they found themselves working on the beach in Bali and still feeling like something's missing.

Read more: Where do remote employees pay taxes?

I took what I knew from my HR experience, which was that the more connected our reasons for working are, to the work itself, the more we're going to feel motivated, inspired, and engage and perform at our best. Our environment of course plays a role in our happiness, but at the end of the day, if you don't love your job in Baltimore, it doesn't mean you're gonna suddenly love doing it in Bali.

It's important for people now that tens of thousands of companies like Spotify and Twitter and Facebook are announcing, you can work from anywhere where you do your most focused and creative thinking. It’s important that people understand that, first, get these fundamentals right. What is it you enjoy about your job? How can you make an impact? What skills do you want to develop and grow? I just don't want people to have this misconception that just because they can work from anywhere they're going to be happier.

How did the timing of all this line up with the pandemic?

Sarah: When I came back to the states after traveling, suddenly it was Covid. The whole world was remote. I came back March 1, 2020, which actually was the planned return date. It wasn’t cut short.

What made me pivot is I felt like there's thousands of people that I can help now understand how to be productive and engaged in their work, regardless of where they're working from. And I helped my company transition a bit into this new way of working, but I really wanted to help thousands of people. I had just finished writing my book, Remotivation. And I felt like, wow, this is an opportunity to really help everyone understand a bit more about what I just experienced and for my background in HR. 

Tell us more about the concept that fueled Remotivation.

Sarah: I did lots of focus groups, surveys, and research with different remote workers in my travels. And I figured out that there was this common theme in those that were most motivated and happy in their work. 

It was these common steps that they were able to take. The first one is they were able to minimize obstacles related to their money, identity, and routines. The second one was optimizing opportunities for growth and impact. And the third was realizing the joy and the benefits of enjoying your work. And so this was this theme. Just to give a couple examples, some people who said, “Well, I'm doing this job because if I didn't, I wouldn't be able to pay next month's rent.”

Or the opposite. We're talking about this money motivator. “I get paid so much that I don’t know how I could do something else, like how could I make the same amount of money, even if I’m now happy?” Once we minimize some of the obstacles related to our relationship to money, our relationship to our identity, meaning who I think I should be versus what I actually want to be or how I want the world to view me. I saw that the ones that were happiest were taking these steps and were the most fulfilled in their work regardless of where they were located. 

You mentioned the importance of community for remote workers. What should remote leaders do to help their teams feel connected?

Sarah: It's going to be especially important as many organizations move into this hybrid model of working where they're going to have some employees come back to the office. Employers are really having to respond to what their employees want, because now how are they competing for talent? It's no longer about the perks in the office. It's about giving employees that freedom and flexibility. So it's important to keep that community strong.

During Covid, we're on one playing field, we're all virtual. But now it's going to be different with some people in the office. So it's important to keep that community. Of course there's lots of team building things that can be done, but most importantly, it's digging into some of the things we talked about, keeping them motivated and inspired and engaged in their work.

What kind of work do they enjoy doing? Are you checking in with them on opportunities that they might want to develop? The skills that they're interested in? Are you helping them understand the impact that they can have in the organization? And I think the more connected they feel to their organization, the mission, the values of the company, the more they're going to feel part of a community, not just a lonely coworker on their own. It's actually getting back to some of these fundamental basics of how to keep people connected to the overall mission of the organization.

How can employees who want to continue working remotely have that conversation with their managers?

Sarah: When I had to do that same thing a couple of years ago, very few people were doing it compared to now. I had to bring the data, the facts, the trends, to show how productive I'm able to be working remotely. Now people have a year's worth of information to show how effective they were and how it's contributing to their performance and engagement with the company. People need to start there.

Are you making sure that you're not just wanting to stay or leave because the company says yes or no, you can work remotely? You have to make sure you're thinking about, how do I want to develop in my career, and do I have more of a chance of doing that in a company that knows me, that knows my performance, that knows my work ethic. Is it worth it for me to say, even though I necessarily can't be remote, is that important to you?

What I often see is people don't start where they are. They think like, “Oh, I'm kind of burned out from the pandemic and I need to change. I'm just going to switch companies in order to do that.” Sometimes that might be the answer, but very often, we can find amazing opportunities in our current organization if we are having honest conversations. 

The truth is that many companies are offering that opportunity to work remotely. It's not going to be as difficult as it was in the past to find those other opportunities. Organizations know this, which is why some of them are trying to be as flexible as possible. But the truth is if your company is not offering it, it's very probable that you could find another one that will.

Sarah: Definitely check out the book, Remotivation. The feedback I’m getting is that it’s helping people create their own version of success. I think at the end of the day, that is the core message. What’s going to make you happy and motivated in your life and in your work, and you just happen to be a remote worker. For organizations, my business is doing corporate workshops and speaking engagements for larger organizations, helping empower your employees to feel connected to their work, more engaged, more inspired.

Connect with Sarah on LinkedIn and visit her website to learn more.

Remote Talks with Sarah Aviram - Living a Better Remote Work Life

Remote Talks: Episode 10 with Jonathan Killeen - Events and the Head of Remote Role

Remote Talks is a series of video interviews with the brightest minds in remote work and global employment, hosted by Remote CEO Job van der Voort. Hopin’s new head of remote, Jonathan Killeen, joins us in this episode to talk about the future of events and what his top priorities are in building the remote infrastructure for Hopin’s global team.

Who are you, and what do you do at Hopin?

Jonathan: My name is Jonathan. I recently joined Hopin as their head of remote. I joined just over two months ago. I'm from Dublin, Ireland.

Hopin is an online events platform where you can create engaging virtual events that connect people all across the world. Very similar to what we're trying to do as remote workers and then dealing with at work globally. We're just over a year old, and how the company came about was actually about our founder, Johnny. He battled with some illnesses in the past, and he was forced into isolation himself. So he had to figure out a way of connecting with people as he couldn't attend events in real life. He's basically come up with a platform that helps people get together, connect, and mirrors the experiences of an in-person event virtually.

Job: And Hopin is one of the fastest-growing companies of all time. Would you say it’s just over a year old? Had about six employees to start?

Jonathan: So as of today, we're at 451 employees. When I joined two months ago, we were 350. The growth is fast. It's scaling really quickly and we're going to continue growing at a crazy pace over the next year. So exciting times ahead.

Jonathan: It's always been remote. I don't think we have much choice, but no, we're very excited to be remote. And I think that kind of mirrors what we're trying to solve for us in our product. We're living that same reality, very happy to be remote. And as you know, lots of pros come with being remote, so we're celebrating those.

How did your role as head of remote come to be?

Jonathan: Hopin is very fast paced. Our leadership are really invested in making sure that we're supporting our employees. We're bringing in people crazy fast, and we want to make sure they're supported, that we're organized internally, that we're being thoughtful about time zones and all of those things that make remote work work. 

My role is actually part of a greater team. We're known as the “vibe team,” and we report into our chief of staff. The team comprises three kind of main tiers. So we have internal comms, we have events, and we have remote operations, all with the goal of creating an incredible culture, something that will scale and just really supporting our employees.

I think it's actually quite unique, the approach we've taken. In the past, I've worked in similar kinds of roles and with similar people, but we've always been across different teams, and we're sitting in different team meetings, and we're not always on the same page. I really enjoyed the setup that we have at Hopin as part of the vibe team. And our goal is just to create good vibes. It's as simple as that.

What have some of your first priorities been as head of remote?

Jonathan: Literally in my first week, I had just joined and we were two weeks away from having our first ever company-wide offsite. It's essentially a quarterly business review/a quarterly kickoff that we were putting into one and using as a chance to unite everybody. I started January 25th, and the event was on February 11th and 12th. I  had to get it across the line and get everything in motion and get things together, but it was amazing.

It was such a great event. It was my first time to plan an event like this on Hopin. We celebrated our previous wins. We looked ahead to the future. We heard from customers. We ran our first ever peer-nominated awards, which was lovely, to give people recognition and celebration, our great employees. 

Events is something I've kind of hit the ground running with right from day one. That's part of the reason I was excited to work at Hopin.

Job: And you do all this using your own platform at Hopin?

Jonathan: We actually dog food. We do a lot of testing ourselves. So for example, we tested everyone in the company joining the all hands, and then we were able to see an issue somewhere and try and fix them before they go to the public.

Job: Is that a common use case for your customers, internal events?

Jonathan: Yeah, and I think initially a lot of the requests were coming in, but we weren't actually looking for business because the volume was so high. A lot of people were looking for these public facing events and these huge conferences and off-sites and things like that. I think the product works so well for all hands alone.

Jonathan: Personally, I've always worked in events, for the last number of years. My focus has always been in-person events. Shifting to the digital world, having interactive elements is one of the most important things. That's something that the platform does really well. When you've joined an event and you can see if you're at the main stage, you can see your presenters, you can see any presentations or decks, but there's also the chat window positioned just to the right. 

It gets people comfortable with interacting. Interactive elements are so, so important. Things that can really help make the interaction work are taking part in polls that are relative to the content or relevance to the content. I think that's great. If there's a Q&A feature where people can be adding questions that can be asked live, and I'm potentially uploading the ones that they like, anything like that, that just means that audience members aren't literally joining a virtual event and leaving it in the background while they work elsewhere. I think the important thing is for sure there's some interaction and to keep people engaged. 

Other things that I really believe in is varying the content. It can get quite monotonous if you're just hearing one person presenting after another.

If you can introduce panel discussions or live interviews or just mix it up, that's really great. Also, try and keep the presentations short. We try to limit everyone to a five-minute max for any presentation. We're always trying to edit ourselves down and be more concise, get to the point quicker, which is difficult for me. Lastly, I would say fun. You have to have fun at events, get creative, and just bring some joy. 

Job: How does scale impact the success of an event?

Jonathan: When you get to a certain range in your audience numbers, it's important to give people the opportunities to interact. Whether it's that they take part in some networking one-on-one or whether you have breakout sessions where they can go into the sessions area. If you have like 200 types of people at an event, tasks can be very hard to keep up with. So yeah, having opportunities to break down into smaller groups is definitely something I would recommend to bring those kinds of nice breakout moments.

What is going to happen in the events world next?

Jonathan: It's exciting times that we're getting back into the real world. But I do think that long term, there's definitely going to be...excuse the buzzwords, but I think the future of events is going to be hybrid. 

We actually hosted a public-facing event on Hopin two or three weeks ago...there was a really nice narrative that resonated with me. They were saying that smartphones once upon a time were called smartphones, but now everyone just refers to them as phones. Online shopping is no longer online shopping. People just say shopping, and similar with hybrid events. One day, we believe that they're just going to be called events. 

Especially in the world of conferences, off-sites, trade fairs, expos, those types of events. I think they'll always be hybrid elements. Whereas we're not saying that concerts are going to be replaced or music festivals, where I don't think you can achieve that moment when the beat drops. We're not trying to get in on that territory.

Are there areas in which digital events are better than in-person ones?

Jonathan: I've actually seen so many examples of these. I think the first one is when I think of the stress of traveling to a city to attend a conference, you have to pack your bag to book your flights. You have to stay in a hotel, all of that travel. If you have kids at home, you have to figure out childcare. All of that combined is a lot of stress. In the future, we're going to have the technology that can actually support people having a choice when it comes to whether they want to travel to their house, and they can still have an amazing experience attending an event from home.

Having the choice would be great because it's not always 100% necessary to be there in person. Another thing we recently did, our first-ever peer-nominated awards of Hopin, called the Hopin Hero awards. It was really fun, but whenever I've done these award shows before in person, I've always wanted to achieve the moments of like the Oscars, where you have all of the people with the cameras in front of them.

But it's too costly to do that, to hire a different cameraman, if you're just running like a simple company event. But when you're doing it virtually, it's simple. The people just come up on camera and then we did a nice applause. That that was something that was really fun, to see everyone's faces, all applauding each other.

Does Hopin plan to gather in the real world in the future?

Jonathan: It's something we're discussing. It comes up all the time, and we're very openly saying yes, someday, hopefully we can make it happen, but we haven't agreed on what that looks like just yet, given Covid and everything else.

What we would be excited to do is...our product is going into this hybrid world. Maybe we'll be able to test our product and do a hybrid event ourselves. So it might not be that we all traveled to the same country, but we might be able to get together in our own countries and groups and join using the same technology and have the same experience and just see what that feels like. That's something that I'm very excited about doing. I think that will be our first attempt. And then following that, maybe next year, we might do something in person altogether.

Talk about Hopin’s growth and the unique experience of doing that fully remotely.

In this episode of Remote Talks, Hopin's head of remote Jonathan Killeen joins the show to talk about his new role and the future of the events industry.

Remote Talks

Remote Talks: Episode 13 with Sondre Rasch - Freelancers, Nomads, and Benefits

Remote Talks: Episode 12 with Ellen Pao and McKensie Mack - Creating People-First Remote Workplaces

Remote Talks with Sarah Aviram - Living a Better Remote Work Life

Remote Talks with Jonathan Killeen - Events and the Head of Remote Role

Remote Talks with Allison Barr Allen - Hybrid Remote and Women in Leadership

Written by • Preston Wickersham

Remote Talks with Tigran Sloyan - Improving Interviews and Evaluating Talent Teams

Remote Talks: Episode 7 with Mac Reddin - Nurturing Communities and Empowering Community Builders

Remote Talks: Episode 6 with Jessica Hayes - Trust and Compensation on Distributed Teams

Remote Talks: Episode 5 with Wade Foster - Global Leadership, Working Async, and International Compensation

Remote Talks: Episode 4 with Darren Murph - Mental Health, Leadership, and Remote Experiments

Remote Talks: Episode 3 - The State of Remote Work, Async, and Offices with Chris Herd

Remote Talks: Episode 2 - Global Hiring, Communication, and Culture with Laurel Farrer

Remote Talks: Episode 1 - Engagement, Bias, and Inclusivity with Tayo Rockson