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Our most valuable learnings from 10 top remote leaders

In our first season of the Building Remotely podcast, Sondre Rasch (our host and CEO of SafetyWing), interviewed 10 of the top leaders currently building successful remote startups. Our goal was to gather information and advice on building and scaling remotely. As we look forward to the next season, we wanted to take a moment and reflect on the most valuable lessons we learned over the past year.

Lesson 1: How to setup a company remotely 

Who: Alex Wellman Topic: Estonian E-Visa
“Estonia might be the first country where people can pay into the public pension system and receive those benefits, no matter where they live… We see a future, where countries not only compete for physical residents, but for digital residents too.”
In one of the first episodes we recorded last year, we talked to Alex Wellman from the Estonian e-Residency about setting up a company remotely. Almost 99% of government services in Estonia are available online. Since 2014, people have been able to set up a company completely remotely by becoming an e-Resident of Estonia. 
What will you need? Requirements for the e-residency include:
  • a passport-sized photo 
  • your government-issued ID 
  • a fee of 100-130€ (depending on where it's picked up.)
You can find more information here.
What are the benefits?
As an e-Resident, you can make use of Estonia's digital government services and startup-friendly ecosystem. However, the main benefit probably comes down to being able to operate your company anywhere in the world, thanks to Estonia’s fully digitalized bureaucracy.
How does it work?
So far, 70,000 e-residents have set up 13.000 companies, which is set to rise even more in the future. For readers interested in setting up their own company in Estonia, we recommend listening to our episode with Alex where he walks us through every step of the sign-up process, as well as the E-residency webpage and this article on insuring your remote company.
In addition to their e-residency program, Estonia is providing their own Digital Nomad Visa alongside countries like Bermuda, Dubai or the Caribians in this initiative.  Check out a full list of Nomad Visas available in 2021.

Lesson 2: How to hire remotely

Who: Matt Drozdinsky What: Hiring Internationally
"If you're hiring an engineer, you need them to be a good coder. But when you hire remotely, you have to put an outsized emphasis on communication skills.”
The Four Stages of Hiring
According to Matt, there are four stages in the evolution of hiring: 
1. Hiring locally
If you hire locally, your talent pool is smaller but you are simultaneously competing a lot less for the available talent. You could even be lucky and attract some extremely talented people to your team, simply because there is no other option available to them.
2. Hiring in different jurisdictions 
For many companies, it has become standard to hire outside of their own jurisdiction (but still in the same country), as it offers great benefits without a strong downside - especially with services like Gusto specializing in making this as frictionless as possible.
3. Hiring in different time zones
A natural next step would be to hire across different time-zones. Especially in a big country like the US, time differences can get as big as six hours in a single country. 
4. Hiring internationally
Almost three-quarters of US companies have difficulties finding the right skilled workers. So if you already hire across time-zones and jurisdictions, why not leverage this and make use of the global talent pool?
Problems when hiring an international team
Essentially, the biggest problem companies face when hiring talent distributed across the globe are the different jurisdictions in each country. Getting an overview of different legal settings is a full-time job on its own and can be intimidating. Initiatives like Pilot aim to solve this problem and make hiring internationally just as easy as hiring talent from down the street. 
Contractors vs. Employees
When you hire internationally,  there are decisive differences between a full-time employee and a contractor:
  • A full-time employee can only be hired by a local company. The only option to hire an employee internationally is to set up a subsidiary in the relevant country.
  • A contractor can be hired internationally, but would need to take care of their own taxes and legal requirements. This can be a trade-off for many prospective employees but is often the only way for SME’s that can’t afford to set up subsidiaries for only a handful of employees in any given country. 
  • Matt’s suggestion to solve the issues an international hiring process brings with it would be to hire a PEO - which gets increasingly accessible for small companies.
Salaries
Since living standards are different around the world - and you want to give fair compensation to all your employees, how can you organize a fair salary structure for your distributed team?
Matt suggested two different philosophies around salaries, without a clear “winner” :
  • Paying salaries that enable the same living standard based on the location of your employees.
  • Paying the same salary to every employee as they have control over their own location - and therefore cost of living. 

Lesson 3: How to onboard remotely

Who: Darren Murph What: Transitioning to remote
“Your culture has to be written down because you may go years without ever seeing a certain colleague or a certain team. And you need to know that without a doubt, they're aligned culturally, which means they're aligned on values.”
Processes to onboard remote employees effectively
When we sat down with Darren to discuss the challenges of transitioning your company to a remote setting, he mentioned that one common pitfall he sees in remote companies is the search for a culture fit: “‘How do I assess culture fit remotely?’, is just fundamentally the wrong question to ask.”
Rather than looking for a culture fit, GitLab is determining values that are important to them as a company and then checking if prospective employees fit those values. 
Additionally, everything relevant in the company is documented in their constantly updated handbook where all systems, values and people contributing to GitLab are documented for everyone to see. This is particularly good for new hires. 
The Head of Remote
Not sure how you could work these processes into your company? Organizing the remote aspects of a company is enough work for at least one full-time position, which is why more and more companies are hiring a Head of Remote.
The job description for this title is still vague and can differ from company to company. You can read more about what a Head of Remote is responsible for, why this position is important and why you might need one in your company.

Lesson 4: How to effectively manage and communicate remotely

Who: Danielle Morrill What: Effectively Working and Managing Remotely
“My goal is to manage teams that hit their goal. And when they do hit that goal, how do we celebrate that win and actually stop and reset?”
Managing Remote Teams Effectively Managing a team remotely is a different job than doing so in an office. We talked with Danielle Morill - the founder of Mattermark and now Senior Growth Manager at GitLab - about her advice on managing remote teams. She mentioned that she sees herself as a coach helping her employees be the most productive version of themselves. 
Below are the four main insights that help in creating a productive environment for remote employees: 
1. Set clear goals for your employees. 
Good communication skills are essential for anyone working, and especially managing, remotely. If you set clear goals of what is expected and what the criteria of success are, you will save yourself a lot of misunderstandings and confusion down the line. 
2. Set realistic expectations
Not everyone's lives and motivation revolves around the company they work for - and this is okay. Be realistic with what you expect from your employees.
3. Acknowledge Achievements
If you set ambitious goals, it is essential that you celebrate and take a step back once you reach them. Creating a good balance while working remotely is not easy, but if you want to reach it, appreciating your team's work (and your own) is vital. Don’t be afraid to give yourself a pat on the back every once in a while. 
4. Create an environment of learning
Mistakes are a normal part of work. Experiments and the drive to learn more should be encouraged. In a remote environment, it's even more important to be very intentional about creating an atmosphere of emotional safety and understanding.  Finding Balance when working remotely
"Am I really allowed to go for a run when my team is working hard on this thing? Am I really allowed to have a two-hour break?"
Managing yourself while working remotely can be a challenge in itself for many. According to Danielle, there are two common pitfalls in this setting:
  • You work more than usual (and often too much), to compensate for the decreased face-time recognition of your work. 
  • The missing office environment can decrease your motivation.
The solution?
Firstly, seeking validation outside of work - Danielle mentioned discovering new passions and ties her validation and fulfillment to things besides just her work.  Second, in order to decrease stress while managing herself, Danielle is very intentional about her schedule and is increasingly embracing the “Managers Schedule” based on a post by Paul Graham. It is both important and difficult at the same time to make sure that your calendar reflects your goals. 
Managing your team during a lockdown
The pandemic crisis has put a toll on almost every company - remote companies included. While there are certain processes you can certainly improve while switching to remote, you also have to be realistic about the morale of your team in times of a global crisis. 
According to Darren Murph, “keeping morale high during lockdown is really hard. And honestly, you just shouldn't expect it to be high right now.”

Lesson 5: How to build a healthy remote culture

Who: Darren Murph What: Transitioning to remote
“I was able to connect more deeply with 135 people spread across 6 continents, than i could have ever done in an office.”
Traditionally, company culture was connected with physical things like free lunches, ping-pong tables and modern office layouts. From talking to remote work leaders like Darren Murph and Spencer Jentzsch (formerly Hacker Paradise), it’s obvious that a strong culture is not confined to co-located teams, but is actually a vital part of successful remote companies.
How do you create a strong culture remotely?
Remote culture is something you need to be really intentional about. While co-located teams can “get away” with not putting a lot of effort into this area of their company (as long as they provide the metaphorical watercooler), remote teams need to intentionally foster a healthy culture from day one. This does not mean that remote companies are at a disadvantage. Remote work allows for better integration into your own life. Remote workers have the ability to show an authentic self to each other and build relationships with each other in ways they are comfortable with. 
As Murph states, “Remote teams have the possibility to connect to each other in a way that in-office teams do not.”
How can you leverage this?
  • Pay attention to your company culture Like with every aspect of your company, your culture depends crucially on your team. And in remote teams it is especially important that you pay special attention to communication skills, alongside being a fit with your company values. 
  • Be clear and transparent
    At SafetyWing we have an internal Notion page in which we write down everything that is going on in the company, including the values we stand for and how we aspire to collaborate (like a small version of GitLabs handbook). 
    This especially helps new hires to understand our culture and to identify how they can contribute to and be part of it. 
  • Provide informal communication channels Opportunities for informal communication are critical in helping people connect and find solutions to difficult problems. Now that the literal watercooler is missing, you need to find other ways to implement this side of your organizational culture. One way to do it would be to create an office style hangout environment with applications like Sococo. Another would be to deliberately allocate communication channels, solely used for informal communication - e.g. Slack channels that delete messages after 90 days. 
  • Establish informal rituals with your team Darren gave the example of a talent show in which the GitLab team would come together and share their unique talents with each other: “I was able to connect more deeply with 135 people spread across 6 continents than I could have ever done in an office.”

Lesson 6: How to build a remote community

Who: Spencer Jentzsch What: Building remote communities
“If you can get other people to invest into the community and build it, and they feel personally invested, they will want to see it succeed. They turn from a passive member of the community, into an ambassador.”
As our attention became the most valuable resource, building loyal and engaged communities is an increasingly beneficial practice. In the first season of Building Remotely, we had the chance to sit down with Spencer Jentzsch - former CEO of Hacker Paradise - and explored the key elements of a strong community.
  1. Build personal relationships Grow your community on a personal level, one member at a time. Make sure everyone in the community feels appreciated and valued. In online communities, posting on social media once in a while is not enough to form a thriving community. If you want to build personal relationships with people, it is important to have regular facetime and engage with every member. You could facilitate this by breaking up your community into smaller communities that are engaged separately. 
  2. Define your purpose
    Before you even start building a community, you should define who are the ideal members and how this community is providing value to them. Without knowing this, there is a good chance that nobody will feel engaged enough to join and stay active within your community.

Lesson 7: How to build products remotely

Who: Steph Smith and Pieter Levels What: Identifying trends and building products for the new remote workforce
In the past year, we had the chance to talk with several entrepreneurs who built or are currently in the process of building their own remote companies and products. But how do you actually identify what to build? How do you launch and grow your product? 
Below we aim to give insights on these questions based on our conversations with Steph Smith (from Trends.co) and Pieter Levels (NomadList and Remote.ok)
How to decide what to build
More than a year after learning to code, Steph published her first projects on ProductHunt and has been awarded the "Product of the Day" title along with the “Maker of the Year” nomination. At Hustle’s Trends.co, she is identifying new and upcoming trends in business. 
So what was her advice on identifying noteworthy developments and eventually deciding what to build?
  1. Train yourself in recognizing something interesting Identify the mechanisms behind the things you find interesting - to eventually replicate them in your own projects. 
  2. Get inspired by the world around you Trends naturally move around the world. Popular movements in Asia could move to America or Europe and the other way around. Sometimes, predicting the future can be as simple as looking to the other side of the globe. If you have a globally distributed team, this is something you could leverage quite easily. 
  3. Is it a fad? How do you differentiate a long-term development and a fad? Usually, fads solve a problem that is hyped and relatively temporary, whereas real trends are subject to a substantial long-term problem. 
    A good rule of thumb here is the Lindy effect. Graph taken from "Long-term investing with the Lindy effect" by Pete Wargent.
How to launch?
  1. Launch Early According to Steph, it is crucial that you set clear deadlines and stick to them no matter what. There is a famous quote by Reid Hoffman saying: “If you are not embarrassed by the first version of your product, you've launched too late.”
  2. Be niche When Pieter created NomadList, it started out as a spreadsheet mainly solving his own problem. At the time, “Digital Nomadism” was considerably more on the fringe than it is now, which made it relatively easy to add to the culture and provide value for a specialized audience. This scene quickly transitioned into the mainstream. According to Pieter: “A scene either becomes mainstream or dies out.”
Growth: VC vs Bootstrapping
There are different philosophies on Venture Capital funding vs. bootstrapping your startup from scratch, and everyone has to find what works best for them. Pieter (a bootstrapper by heart), had an interesting standpoint on this: 
“When bootstrapping your startup, you are so tapped into the markets that anything you do to your startup or website, you immediately see if it works because you either make money or not. And with VC, you have all this money on your bank accounts and there isn't enough incentive to build revenue or profits, resulting in a more vague connection to the market. So you can do a lot of BS as a startup. And I think that's a disadvantage."

Lesson 8: How to build a remote lifestyle

Who: Andreas Klinger, Austen Allred and Pieter Levels What: The future of Remote Work and Digital Nomadism
“I can hire you a better engineering team in Nigeria - easily - than in San Francisco”
New forms of education and hiring
Austen Allred is the founder of Lambda School - a CS education that is free until you get a job. On one hand, this is affordable to almost anyone. On the other hand, it forces Lambda School to do everything in their power to connect their graduates with relevant job offers. From this promise, a new hiring process is established in which the educational organization has full responsibility for their work.
New hiring processes
With companies not hiring solely based on a university degree anymore, how could you make sure a candidate has the right qualifications?
There are a couple of ways to facilitate this through work trials, a coding challenge or the traditional method of taking a test. On the other hand, Austen would encourage employers to pay less attention to interviews alone: “People who can talk fast, get hired more often because the interview is basically a talking test, if you think about it.”
A new remote workforce
With coding education getting more accessible, one of the most powerful skills in modern history could spread even wider, causing tremendous global impact according to Austen: “I think about how powerful it would be if literally everybody in the world could write code as well as a Google engineer. Nobody would be worse off in that instance.” And thanks to remote work, this development doesn't only take place in Silicon Valley but on a global scale. 
New Lifestyle of the remote workforce with Pieter Levels
“The social communities in the place where you're born might not fit precisely with the social communities that you're supposed to be with.”
The next wave of Nomads?
Pieter Levels predicted the number of Digital Nomads to rise to one billion by 2035 - a number quoted by The Economist, among others.
After the initial wave in 2007, and the second wave caused by emerging remote startups and freelancers working remotely, the third wave includes a new majority of travelling families, which is likely to form as one of the lasting effects of Covid-19. 
But this new wave of nomads will have new challenges - they will need structures in place for childcare and education opportunities while in search of new communities and potentially safer travel and accommodation. Those problems are potent business opportunities.
Challenges of Digital Nomads
With the possibility of working remotely, many would be able to fit their place of residence to their current lifestyle, which can result in uniquely fulfilling communities. But creating a strong sense of community is still one of the biggest challenges in the Digital Nomad scene, as much communication is facilitated online and face to face interaction often only lasts a few weeks.
Some of those challenges could be addressed by remote work hubs, competing for talented remote workers and digital nomads. 
Second Degree Effects with Andreas Klinger
"(Right now and in the future), every company that will work digitally, will have a remote aspect."
The effect of remote work on our cities
If there are one billion people choosing to be location independent - and regularly relocating - what effect would this have on our communities and our cities? With fewer people commuting and less central housing used for office space, major cities have new possibilities to restructure themselves and become more liveable.
As Alex from the Estonian e-Residency states: “We see a future, where countries not only compete for physical residents but for digital residents too.”
Alternatively, some remote workers have already started creating remote work villages, although not everyone is convinced of the sustainability of those communities. Pieter: “Instead of trying to create new villages, which reinvent the whole console society, try to iterate on the society you're currently living in.”
For a more analytical view on the effect of remote work on our cities, you should
How companies will change
It's likely that most companies that can work digitally, will be partially or fully remote in the (near) future. What does this mean?
As mentioned before, companies will compete for talent on a global scale, which evens the playing field and allows for talent to choose from a global pool of employers. With your team remote, many companies will likely take the opportunity to save on office space and rather present their HQ as an “Apple Store showroom” - as Andreas Klinger suggests. 
Furthermore, some roles might disappear and new ones will emerge. 
Overall it is likely that companies will take a different role in the life of their employees, once they are not forced to plan their life around their job but their life with it in symbiosis.
New business opportunities
According to Andreas, not only the global pandemic but also remote work in itself brought many business opportunities with it: “Many founders are building companies right now that will be important after this recession.” A significant number of originally offline companies are in the process of moving online - think of coaching, fitness and even teaching - and many are here to stay. Andreas described concierge services for SaaS tools as one opportunity he sees in the current market. 
A new workforce, new types of companies and potentially new cities will be created as result of remote work. This will bring countless new business opportunities with it, some that we probably can't even imagine right now.
Building Remotely is a resource that brings together the experience, knowledge and insight of top remote founders and thought leaders, making the world of remote the best as it can be. We hope you join us for the second season of the Building Remotely podcast.

About the author

Jakob Bodendieck

Podcast Production Manager
Jakob is a startup-oriented nomad, currently finishing his BA in Creative Business in the Netherlands. He joined SafetyWing as a Podcast Production Manager and helped create and grow the Building Remotely podcast. As the host of his own podcast, The Self Employed Student, he is offering a valuable resource for other young people with an entrepreneurial mindset.