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Why you need a Head of Remote

This article was written in partnership with Running Remote, the world's largest Remote Work conference. You can still get a free ticket for their next online conference — 18 November 2020! Earlier this year, we launched the Building Remotely podcast with a goal to collect knowledge from the top remote leaders around the world. We recorded our first two episodes by interviewing two leaders with the title, Head of Remote. Andreas Klinger began by discussing what the future of remote work might look like. At the time he was the Head of Remote for AngelList (he has since left to focus on Remote First Capital). Darren Murph, Head of Remote at GitLab, gave insight on how to transition to remote work.   These two guests got me thinking: what is a Head of Remote? What do they do? Why would a company hire them? We are currently at the cusp of realizing what remote work can accomplish and how it will change our world. Such a shift will likely create a host of unheard-of roles in the future, so I wanted to dive into what appears to be the start of that movement. I was surprised to find out that both Forbes and TechCrunch had recently dug in as well, but put the content behind paywalls. It seems others are curious about this new role as well. 

What is a ‘Head of Remote’? 

Like all new concepts (including remote work), the title Head of Remote doesn’t have a set meaning. It likely never will. When asked directly, Klinger stated “Nobody knows what this role really means, including me.” Every role in a startup (or any company which operates like one), is defined by needed outputs, or problems that need to be solved. A Head of Growth is responsible for the long term growth of the company. A CTO is responsible for the tech. 

So to answer the question, “what is a Head of Remote?”, I’ll start by reframing and answering the question: what outputs are needed from a thriving remote company? Every company and team is unique, but I can point out some obvious ones that are universally true for a remote company. Even if you just recently became one.  What outputs are needed?

  1. Cultivate a healthy remote culture

  2. A system that allows the remote company to operate smoothly 

  3. The ability to hire and onboard the best remote talent

  4. Develop products and features that appeal to the remote world 

From the outputs above, we have a clear answer to the question. A Head of Remote ensures that the company thrives in every aspect of remote work. It’s unique in that the responsibilities are both internal and external. You first have to ensure the internal mechanics operate smoothly. Then, make sure the rest of the world (and people you want to hire), know it to. After all, it’s not enough to just offer remote work anymore to attract the best of the best.

What does a Head of Remote do?

1. Cultivates a healthy remote company culture 

A Head of Remote must work on clearly defining the company’s remote-first values directly with the founders or leadership team. Appropriate feedback mechanisms need to be in place for the entire team (including the top). This includes anonymous feedback, and also regular check-ins with team members to make sure they are doing well remotely. 

They also are responsible for having a “fun” remote work environment. This isn’t as difficult as many make it seem. It starts with having common-sense policies that encourage a positive remote work attitude. You can also still have non-work related events and communication channels. GitLab has devoted 100% of their Slack communications to informal communication (seriously). Once we are past the whole pandemic, designing and planning in-person meetups also plays an essential role here.

2. Develops systems which allow the company to operate smoothly

What’s your company’s “remote-tool stack”? What are the expectations for working hours? Is it synchronous, asynchronous or somewhere in between? These questions need to be addressed directly, and communicated clearly and openly. If your team thinks that they are gaining clout for answering emails 24/7, they will burn out (and probably annoy the rest of the team). 

You also need to dictate what exactly communication channels are for and how they are used. Small things have a big impact here. It’s easy to hit the ‘forward’ button on a massive email chain when you are busy, but it would be much better to summarise the thread. These things need to be outlined before animosity builds. Complex tools like Google Drive and Notion also need to be neat and tidy for smooth remote operation. These things don’t happen automatically. 

3. Hire and onboard the best remote talent

Similar to how job applicants work to cultivate their resume, LinkedIn and portfolios to look good, companies need to do the same. It’s not enough to just be remote anymore. Potential hires (at least the ones you want), are likely looking for a solid set of remote benefits. This helps show that you are truly a remote-first company with accompanying values. Make sure all of these things are communicated in job descriptions, and that these postings are finding the right potential candidates. This helps ensure the hires match the company’s own values. 

It doesn’t end at the point of hire. Onboarding a remote employee is a whole different game when you never meet them face to face. Make sure the first week isn’t a blur of confusion and anxiety. Being fully integrated with the team is absolutely essential for new remote employees. Accomplishing this isn’t a small task. Create a clear and repeatable onboarding process that the whole team is aware of. This not only makes remote life more pleasant, but also ensure the new hire you worked so hard for hits the ground running from day #1. 

4. Develop products and features that appeal to the remote world This is the only category that isn’t universally applicable. Still, most remote companies do in fact cater to the remote world with the product and service offerings. If your company does this at all, you need to research emerging needs and trends within the remote world. You can do this by coordinating with remote leaders of other companies and expanding the team’s network. Part of this is being a thought leader in the remote space and among similar communities. Oftentimes, a Head of Remote can act (at least partially) in the role of a Product Manager as well. If you have already built a seamless system of remote communication for the company, perhaps you can streamline processes across individual teams and products as well. Ultimately, you must make sure that your products and features function well within the rapidly evolving remote world.

Who should hire a Head of Remote?

If you are a remote company, you will need to do #1-3 above regardless. That means that someone should be handling these responsibilities. Especially if you are a younger startup, you may not need someone to focus on these specifically. After all, if you are just starting a company, the founders must play all of the roles themselves. Lots of other top employees can play the role. The CEO, COO, Head of HR… these can all work. Honestly, anyone passionate about remote work can thrive in the remote role. The important thing is that they are a leader within the company, and have an open line of direction with the founders or executives. 

This can actually be a good indicator. If a company doesn’t have a foundation in remote work, this is something they should certainly hire for. Maybe you are a company who, during the pandemic, decided that they would never go back to the office. This is a difficult transition, and no one gets it right on the first try. Unless the founders have an experienced background in remote work, you’ll probably need some help. 

Maybe your company has been remote from birth (or for nearly a decade, like GitLab). Now that remote work is becoming more of the norm, you have to do something truly remarkable to stand out as a top remote company. Hiring a Head of Remote is certainly one way to do that. Having a bit of a PR evangelist to get you attraction ensures the top talent that you are not only a remote company, but the best remote company. 

At the end of the day, the biggest indicator that you need someone for the role is struggling. There’s no shame if your company is struggling with remote work. The chances that you are scoring a 10 with regard to remote culture, process, hiring, onboarding and collaborating are… unlikely. If you feel that there are problems, there certainly are. But you don’t have to hire a full-time Head of Remote to deal with most of these issues. Trying to fill the role yourself is a good start, but remote work has evolved to the point where there are experts who can help you. 

How to find a Head of Remote?

So you’ve decided you need a Head of Remote in some capacity. Congrats! That’s an exciting step for your remote company. But you’re now likely asking, ‘where do I find one?’  

This will, of course, depend a bit on what kind you are looking for. Are you ready to hire someone full-time? Part-time? Do you need them to do all of the things above or only some? How much can you afford (or willing to pay)? Keep in mind, you can have any answer to these questions. It’s just helpful to know what and who you are looking for before the search begins. Once you’ve put some thought into that, here are some places to start. 

Location 1: look internally 

This is a key hire that, by nature, needs to understand the company’s mission, vision and culture. They need to have a key and direct relationship with the founders/executives. So if possible, look internally for someone who is ready and excited to fill the role. Keep in mind, you don’t have to push someone instantly into a full-time Head of Remote. Even if you feel you are at that stage, it would probably be better to have someone internally start working on it 25-50% of the time than someone from the outside starting at 100%. 

Location 2: look at your network 

As with any hire, it’s a huge bonus if a candidate is “in-network”. They may not yet be a part of the company, but they are more likely to understand you and your team. Ask team members who emulate your culture and truly believe in your mission if they know anyone who would fit the role well. You might be surprised what your core team comes back with. By the way, if you don’t already, this is a great practice to start a candidate hunt no matter what the role you are trying to fill is.

Location 3: find your ideal candidate manually 

If you don’t have anyone in the company or know of anyone in your network who is a perfect fit, don’t fret. It is, after all, quite a niche role. But now it’s time to think critically about who your perfect candidate would be. Think of the remote thought leaders you follow. Who would you consider the dream candidate? Chances are, that person won’t be available (although don't’ be afraid to try. Even if they aren’t available, they may know someone who is). Not to worry. Once you have this outlined with a few names, you’ll find it much easier to expand the search and get a shortlist of people you are excited about. Reach out to them and start a conversation about what you are looking for. 

Location 4: post a job listing 

If all else fails, go the more traditional route and post a job listing. You’ll likely get a lot of poor fits applying, and you’ll have to spend a LOT of time vetting people. Still, it’s a great way to get publicity about the new hire. Even if 1 out of 100 people who apply is potentially a good fit, statistically you are in good shape. Just be sure to put a lot of time into the job description, and be thoughtful about the right places to share it.

About the author

Sam Claassen

Head of Growth
SafetyWing

Sam Claassen is the Head of Growth at SafetyWing and a serial advocate for remote work. A longtime nomad himself, he has been to 65 countries while doing growth and remote work consulting for startups and accelerators. Through his work at SafetyWing, he is working with a team to create BuildingRemotely.com – a podcast, online resource and soon to be book on building a thriving remote company.