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Staying Remote? Hire a Remote Work Leader

June 26, 2020
Linzi Nield
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COVID-19 could cause a permanent shift towards remote work, even after the virus is under control.

Fifty-four percent of Americans want to keep remote work as their primary mode of work, and seventy percent say they’d like it to at least be an option. But “remote work” and “working-from-home” are not the same thing. “Working from home” is a temporary situation; “remote work” is permanent, and requires a deliberate foundation of processes built around working outside of the office. 

Regardless of whether the pandemic forced your team to create a patchwork of ad hoc processes, or your organization has been working from home since before it was cool, it may be time to centralize these processes under a senior leader: It might be time to hire a Head of Remote.

Hiring a Head of Remote is uncharted territory for most organizations, and most candidates likely won’t have “Head of Remote” on their resumes. That’s why we’ve put together this list of things to consider when hiring a Head of Remote. 


What is a Head of Remote?

Before getting into hiring, it’s important to be specific about the roles and responsibilities of a Head of Remote. This is likely a new role for both you and your candidates, so there are no “rules” per se. But in our experience, a Head of Remote usually works with company leaders on strategy, structure, and process around the hiring and management of remote teams. 

It’s a wide purview, and a Head of Remote’s work often cuts across several functional areas.

“I sit at the intersection of culture, operations, people, talent branding, marketing, and communication,” says Darren Murph, Head of Remote at GitLabs tells Terminal. “My most critical responsibilities are to ensure that GitLab team members acclimate well to remote, give themselves permission to embrace our values and operate with remote-first workflows, and are equipped to share our learnings with those outside of the organization.”

A Head of Remote’s job boils down to equipping the org with what it needs to successfully hire remotely, and putting processes in place for remote workers to be efficient and happy.

Pro tip: Put together a wishlist of the processes and tools you need for remote work at your org. It will help you put together a job description as well as understand the gaps in your company today.

Understand where your org stands today

Chances are that today the roles and responsibilities around remote work are spread across several functional areas in your org. So before you start the recruiting process, it’s important to know what functional areas are responsible for your remote work now, and how your status quo will change. 

Does your HR team manage most of the processes? Is it spread out across recruiting staff, eng teams, and the team in charge of procuring internal work tools? Is it completely ad hoc? Answering questions like these will give you a good lay of the land to show how a Head of Remote could off-load work from existing teams and possibly interrupt their flows as well

Pro tip: Do an internal audit with your exec team and see how remote responsibilities are segmented across your org today. Once you understand the lay of the land, you can see how this new role would fit into your org, as well as compare it to your wishlist. (An audit may also help get buy-in from execs because you’ll show how you’ll offload work from their teams.) 

Define your metrics of success

Once you know why you need a Head of Remote, it’s time to lay out a framework for measuring how this person will achieve their goals. Most experts say that hiring a Head of Remote is about building a systematized approach to trust, so a mix of hard and soft metrics is paramount.

The KPIs important for a Head of Remote are similar to those that People teams care about: retention, employee NPS, and upward feedback scores are all critical metrics, especially since poor remote management practices can have a negative impact on morale and retention.

“The three most important KPIs for a Head of Remote in my opinion are knowledge assessment metrics, culture survey results, and the average recency of company handbook updates,” says Murph. “It’s all about building a positive culture around remoteness.”

“Employee surveys that measure levels of collaboration, worker satisfaction, and overall trust in management structures will give your team a sense of where work needs to be done,” says Jennifer Farris, Chief People Officer at Terminal. “We recommend this regardless of your plans for a Head Remote, but it becomes even more important when putting these responsibilities under a single leader.”

Here’s a list of KPIs to we recommend considering when defining your success criteria for a Head of Remote:

  • Employee satisfaction: Retention, employee NPS, and upward feedback scores
  • Organization communication: the number of meetings scheduled and their efficiency
  • Productivity: metrics such as goals completed and the usage of tools that have been implemented

Pro tip: Get a sense of where you stand today to provide a baseline for measuring future success. Employee surveys around collaboration, well-being, and others are important to measure the health of your workforce. (This is true even if you don’t have plans for a Head of Remote)

Get buy-in from your exec team

Adding a Head of Remote isn’t like building another story on top of an existing building. It’s more like jacking up the entire building and adding more to the foundation. It will take structural changes for remote work to truly take hold at a company, and for that reason it’s key to heavily involve execs in decisions along the way. 

“The biggest challenge of hiring a Head of Remote is reinforcing to everyone that they must drop prior organizational baggage and truly operate differently,” Murph says. “Remote-first requires a great deal of unlearning. For example, operating with a bias towards asynchronous workflows feels unnatural for many who join with decades of experience in a conventional corporation.”

And this type of buy-in needs to come from the very top. It’s best to get a deep understanding of what your execs need out of remote work. 

Pro tip: Sit down with each exec and ask them what they’d want out of a Head of Remote. What are their concerns? What are their hopes? What do they want taken off their plate? When your entire team is heard, they’re more likely to buy into structural changes to your company. 

Get creative about your recruiting pipeline

Recruiting for a Head of Remote won’t be like recruiting for established roles like VP of Sales or CMO, where you simply reach out to existing sales and marketing execs. The Head of Remote position is one that largely doesn’t exist, and to get top talent, it’s important to keep an open mind about the talent pool you’re going after. Recruiting will take creativity. 

“The Head of Remote is a unique role that is not patterned like any prior executive role in traditional management,” says Murph. “Leadership teams should hire for deep remote experience — there is simply no substitute for experiencing the evolution of the workplace from outside of the conventional office.”

“Ideal candidates will be excellent storytellers and servant-leaders who understand the nuances of culture while showcasing the skills necessary to create unity in the midst of organizational transformation,” Murph adds. “It’s a role that requires operational savvy, people management sensibility, and a penchant for precise communication.”

HR talent pools can be a good place to start, but we’ve also seen successful Heads of Remote come from other parts of the org. Murph himself, for example, was a CEO and Editor-in-Chief in a previous life. AngelList’s former Head of Remote, Andreas Klinger, was previously a CTO.

Here’s a checklist of important attributes to consider when sourcing and interviewing candidates:

  • Experience with remote work
  • Understanding of how people operate when remote, including the mental and physical challenges they face, what different personalities need, and how to build trust with teams
  • Understanding of OD/OE (Organizational Development/Operational Excellence) principles
  • Expertise in interpersonal communication
  • Experience within management-level roles 
  • Deep familiarity with the collaboration tools on the market
  • Experience as an influencer within exec teams

Pro tip: Instead of looking for similar titles, which may severely limit your candidate pool, refer back to your wishlist and think about where you need the most help. Is it in recruiting? Sourcing collaboration tools? This will help you prioritize the people you go after. 

Also, you can appeal to potential candidates by stressing their control in defining the role – not only for your company but in the industry as a whole. They’ll be pioneers in the field, which means they’ll be able to set up processes and best practices in your org and beyond.

Be patient onboarding your Head of Remote

So you’ve hired someone! Now the hard part begins. A Head of Remote will likely touch every single functional area at your company, and that’s exactly why it’ll be critical to methodically acclimatize your Head of Remote to how your company works. 

It’s important to make sure your new Head of Remote is very in tune with your company culture before they get to work. They’ll be introducing new work processes and tools; as such, you want the changes to augment existing working conditions, not go against the grain.

“Your remote strategy is a part of your talent strategy,” says Farris, “so embedding this role with the leadership team for some period of time will be critical to really get to know the business, how people operate, and what the intentions are. This role needs to have a strong understanding so that they can influence where relevant as well.”

This all adds up to not being afraid to give your Head of Remote a longer onboarding than usual. And be sure they get in-depth information about your current work processes, including edge cases because oftentimes exceptions prove the rule.

Pro tip: Consider devoting the first month of your Head of Remote’s tenure exclusively to observing how your org works. That way they’ll be familiar with what makes your team tick before changing how everything fits together.

Remote work goes beyond COVID-19

Remote work will be a necessary fixture of the post-COVID world. And like any other important aspect of your business, to be successful you’ll need to be deliberate about the structures you put in place.

A Head of Remote is largely uncharted territory, but for many orgs, so is remote work itself. Being intentional about how you adapt to the demands of the post-COVID workplace will set your team — and your entire business — up for success.

Want to learn more to set your team up for remote work success? Download Terminal’s complete guide to remote onboarding.

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