Why Your Company Needs a Head of Remote

05/10/2022 7 min read
Caroline Castrillon is a career and life coach who founded Corporate Escape Artist after a successful 25-year corporate career. She has held executive leadership roles in small tech firms, as well as Fortune 500 companies including Dell and Sony. In addition to Toptal, she contributes to Forbes and Thrive Global, and she has been featured in The New York Times, Entrepreneur, Inc., and Success magazine.

The share of employees working from home has grown exponentially over the last two years: Pre-pandemic, only 6% of employees worked primarily from home and roughly 75% had never done so, but by May 2020, over one-third of employees were working remotely. According to data from Ladders, a quarter of all professional jobs are expected to be remote by the end of 2022, with nearly 15% of all high-paying jobs operating remotely as of August 2021.

Now that remote work has become mainstream, companies are enjoying the ability to hire top talent regardless of location—but they need to be mindful of building a remote-first culture to get the best results. According to Charlie Warzel, co-author of Out of Office: The Big Problem and Bigger Promise of Working from Home, that’s where hiring a head of remote (or chief remote officer) becomes invaluable.

Too often, companies push remote management to departments like human resources, which Warzel sees as a mistake. “HR teams are already dealing with lots of pandemic fallout issues, high quit levels, and staffing and rehiring challenges,” he tells Staffing.com. “Burdening them with all of the remote tasks and projects could pose a logistical challenge.”

With the rise in hybrid work, Warzel explains that having a head of remote can help level the playing field for both employees working remotely and those who are in the office. “I think it makes absolute sense to have someone whose sole focus is designing a hybrid work program and managing remote workers—everything from tax considerations to office setup and technology,” he says.

Darren Murph, Head of Remote at the all-remote DevOps platform GitLab, is said to have pioneered the role, which he describes as sitting at the nexus of strategic communications, marketing, and operations. “My team is responsible for documenting and evolving GitLab's unique ways of working,” he tells Staffing.com. “A big part of my job is collaborating with all functions of the business to elevate remote work at GitLab, creating leverage for talent branding, recruiting, awareness, and beyond.” Murph, who has been in the role since 2019, openly documents his work practices and has published an open remote playbook.

Job van der Voort, CEO of Remote, which provides HR solutions for distributed teams, agrees that more organizations are recognizing the growing need for a dedicated resource. “Companies are realizing that having someone solely focused on supporting and promoting their remote team is the most effective way of creating a harmonious and productive remote or hybrid workforce,” he tells Staffing.com.

A report from T3 Advisors in August 2020 showed that of the 95 tech companies surveyed, the number with dedicated remote work leaders increased from 2% in August 2020 to 15% by February 2021.​​

What Does a Head of Remote Do?

According to van der Voort, a head of remote or chief remote officer is responsible for managing the virtual employee experience and implementing best practices for remote work. This role handles a range of essential functions:

  • Serves as a dedicated internal advocate for remote workers. A head of remote collaborates with other internal teams—including business operations, human resources, and IT—to build a remote work infrastructure. This may involve writing or updating company policies, implementing strategies to boost employee engagement, and planning and rolling out training programs. “Having a single, dedicated advocate is especially important for hybrid organizations, where the experience of converting to remote work varies for different employees in different regions,” says van der Voort.
  • Develops and maintains tool sets to support remote work. This includes finding and experimenting with new digital tools—collaboration software, video-conferencing platforms, project management systems, and cloud storage solutions—and developing best practices, habits, and behaviors around working digitally.
  • Champions asynchronous work and DEI. “The head of remote role is just as much about inclusivity as it is about productivity,” says van der Voort. “This person helps create and update company policies to ensure that they consider the needs of a multitude of lifestyles and circumstances.”
  • Tells the organization’s story of flexible work to the world. With more job-seekers gravitating toward remote opportunities, van der Voort recommends having a dedicated leader who can build the company’s talent brand as an innovative, remote-friendly organization and help showcase its remote work fluency in the company’s job postings and on their careers page and social media.

Arif Ansari, Head of Remote Operations at Limeade, an employee health and wellness company, describes his role as a mix of operations and process improvement, HR and people-related functions, and IT support. “It’s almost like a futurist, predicting where we're going to be three years from now as technology keeps shifting.”

Ansari focuses on finding, developing, and experimenting with new digital tools. For example, he uses Limeade ONE (the company's proprietary engagement tool that allows employees to connect with coworkers and receive company communications) and Microsoft Teams to foster internal collaboration and asynchronous work among remote workers. Ansari is also testing an email scheduling tool that will allow employees to pause their inboxes so they can focus without interruptions.

A head of remote is also involved in building operational infrastructure for remote work, which often includes writing or updating remote work policies. For instance, Remote’s employee handbook includes guidelines on how to run a meeting and provides details about the company’s culture of documentation.

According to Warzel, another big part of the job entails surveying employees to identify how the company works best. He cites Dropbox, which evaluates its levels of productivity and engineering performance, and then pairs that information with detailed employee survey data. “The role of a chief remote officer is to find that spot where both of those align, and to present that to executive management to help restructure the corporate culture in a way that benefits everyone,” Warzel says.

Benefits of Having a Head of Remote

As GitLab’s Murph tells Staffing.com, hiring a head of remote is a clear signal that remote work isn’t merely allowed at an organization, but is encouraged and supported. A designated leader shows candidates that the company is committed to creating a flexible and inclusive work environment.

“Remote work requires intentionality,” Murph says. “Designating a leader to ensure that the nuances are considered enables a company to remain focused on bolstering its organizational infrastructure, from tooling to learning and development.”

“Whether you’re in a hybrid organization or going remote-first, you can’t leave the employee experience to chance,” says Chase Warrington, Head of Remote at Doist, the company behind the asynchronous messenger Twist and the Todoist task app. “Without someone who has the space to dedicate energy to remote work, you’ll likely end up with a mediocre result.”

A leader of remote work also helps to ensure clear, timely communication with off-site employees. A McKinsey survey found that remote workers are more likely to experience anxiety if their employers don’t share detailed plans and guidelines for remote work, and that employees who receive more detailed communications are likely to be more productive.

According to Amy Mosher, Chief People Officer at the human capital management company isolved—whose clients include 19 Burger King and Panera franchises via Pride Restaurant Group—a chief remote officer should help build trust between employees and leadership by ensuring that core benefits are evaluated and considered as employee experience drivers.

In addition to boosting employee trust and peace of mind, a head of remote provides companies with a competitive edge when it comes to recruitment. By marketing a remote-first model, employers send the message to potential candidates that they value the whole person rather than just the work they produce, says Ansari of Limeade.

How to Hire a Director of Remote Work

Before bringing on a head of remote, Warrington says companies should answer the following questions to help identify the right candidate:

  • Are you in construction mode or maintenance mode? If the former, you’ll want a change agent with experience building a remote infrastructure. If the latter, you should look for someone who understands your organization but can also provide a fresh perspective on your current operations.
  • Do you want to attract top-notch remote talent and position yourself as a leader in the remote space? If so, Warrington suggests looking for someone with public speaking and writing skills who is comfortable acting as the face of your company.
  • Do you want to build a remote workforce, or a hybrid or co-located environment? Depending on your goals, Warrington says you should invest in someone who has experience with remote or hybrid workforces, and who can provide the documentation, tool set, and best practices to implement in yours.

In Doist’s case, Warrington says the company was already 100% remote with established best practices implemented, so it was important to find someone with external advocacy experience and an understanding of the business' internal processes.

According to van der Voort, the HR sector is the best place to look for a head of remote. “HR professionals with regulatory experience and others with a strong background in setting up new workplace cultures and managing organizational change will be best suited to this emerging skill set,” he says.

“Great remote leaders are, first and foremost, excellent storytellers and writers,” GitLab’s Murph says. “Crisp messaging and expert communication skills are necessary to steward organizational change.” He also says it's vital that they have demonstrated experience leading distributed teams, thrive in ambiguity, and default to challenging preconceived notions. “At its core, this role serves to build the future of work while galvanizing others to contribute,” he says.

Organizations Leading the Way

Remote work is here to stay, and with high profile companies like Meta, Okta, Doist, Cleveland Clinic, and Dropbox hiring remote work leaders, others are sure to follow. Warzel says, “If you're looking to navigate the next five years, [you want] somebody on board who can really tackle these issues and make sure the company is responding in a way that's beneficial to workers and to the company.”

Van der Voort of Remote agrees. “More and more companies will see how transformational this role can be for building their reputation as a great place to work,” he says. “A company that can hire great talent regardless of location will always have the upper hand, and a head of remote will help to maximize this incredible potential. It will be an exciting evolution to follow.”

Caroline Castrillon is a career and life coach who founded Corporate Escape Artist after a successful 25-year corporate career. She has held executive leadership roles in small tech firms, as well as Fortune 500 companies including Dell and Sony. In addition to Toptal, she contributes to Forbes and Thrive Global, and she has been featured in The New York Times, Entrepreneur, Inc., and Success magazine.