Should companies with a large number of remote employees have a leader of remote work? It’s an interesting question and one that more leaders are asking themselves as they devise their future workforce plans.

Whether or not an organisation needs a leader of remote work is dependent upon a variety of factors, some of which are admittedly intangibles, and are strongly related to the degree of trust and confidence the chief executive has in her or his team. When considering whether your organisation needs a head of remote work, it’s helpful to consider these questions:

  • Are company leaders on the same page, or are there some that create exceptions to established rules?
  • Are the organisation’s policies clear, comprehensive, and well understood, and is there a function in place for continually evaluating and evolving them? Or does the organisation tend to have a more reactive approach to creating policy?
  • Is the organisation able to support remote workers, and the exponential complexity a distributed workforce brings concerning the administration of payroll, taxes, benefits, and other compliance requirements?
  • Does the organisation have a distinct culture that contributes to its competitive advantage, and which leaders invest time and energy in strengthening? Or is a healthy, consistent culture an aspiration?

It’s also important to look at where your organisation is in terms of maturity for remote working. Companies at the beginning of the maturity curve have employees working remotely, but haven’t made significant changes in policy or processes designed to optimise the remote work experience for workers and, for that matter, the company. At the other end of the spectrum are companies like Automattic, GitLab, and Basecamp, all of which had fully remote workforces well before the pandemic. Here’s an example from Automattic’s website:

“This isn’t your typical work from home job. Everyone works from the location they choose. We’re spread out all over the world in more than 70 countries…Because of the geographic variance, we’re active 24/7. We care about the work you produce, not just the hours you put in.”

What does a leader of remote work actually do? 

The role and responsibilities of a head of remote are intrinsically based upon where the company is on the maturation curve and its aspirations for remote working. If the organisation needs to build its entire process for remote work, which ranges from developing the digital infrastructure to facilitate remote working, to the various operational, HR, and compliance policies necessary for a fully remote organisation, chances are good the organisation needs expert leadership in developing a remote workplace – likely in the form of a leadership working group and/or a specialised consultant.

“This is where it’s critical to understand the difference between constructing a remote work program and maintaining a remote work program,” writes remote work strategist Laurel Farrer in an article for Forbes. “The former requires extensive experience in virtual organizational development, but the latter can be fulfilled by anyone with a passion for workplace flexibility.”

Aside from the technical, logistical, policy, and regulatory aspects of developing a remote workforce, the challenges a head of remote work will likely face are many and varied. One example is embracing flexibility in terms of not just location but timing.

“Both employers and employees will get the maximum benefit from hybrid work if it is combined with other forms of flexibility,” said Gemma Dale, a lecturer at Liverpool John Moores University, in an article for PeopleManagement by Caitlin Powell. An example is asynchronous work time flexibility, which can free employees from old ways of working that aren’t suitable for everyone.

Another challenge is ensuring that all workers – not just those who can work from home – can enjoy a degree of flexibility, while still ensuring that goals and performance metrics are all met. For organisations with teams who operate in an industrial setting, flexible work options can include enabling people to select their shifts, swap shifts with other workers, and volunteer for overtime (rather than being forced to work overtime on shifts the company designates.)

A noteworthy example is offered in a case study by workforce scheduling provider Shiftboard, in which a company that had struggled with mandatory overtime switched completely to allowing employees to volunteer for overtime work. The results were immediate and outstanding – the company was able to fill almost 100% of overtime shifts almost 100% each week – a significant improvement.

A succinct description of a leader of remote working was offered by Shannon Hardy, who was named vice-president of flexible work for LinkedIn in April 2021, in an article for Raconteur by Jonathan Weinberg:

“Our work includes updating the company’s talent policies; supporting managers in leading their hybrid teams effectively; and ensuring that hybrid working is equitable for all. We’re constantly listening, learning and adapting our approach to improve our employees’ experience.”

Remote and hybrid work is being adopted permanently by a broad range of industries, including several global giants such as British Airways, Deutche Bank, Novartis, Siemens, and Hitachi, to name just a few. (See a growing list here.) For leaders of smaller enterprises, this trend creates a number of challenges and opportunities that a head of remote can help the company meet and embrace:


  • Maintaining vibrant in-office culture and collaboration that has been proven to contribute to performance
  • Supporting employees who wish to “work from anywhere” both in terms of infrastructure and compliance
  • Staying abreast of changes and trends in remote working and related employee benefits, when you don’t have a huge HR department supporting the organisation.


  • Embrace the ability as a smaller organisation to quickly test new ways of working and policies
  • Compete for talent beyond the local talent pool
  • Improve employee retention by offering flexibility in terms of both location and schedule
  • Cutting overhead costs associated with offices e.g. rent, heating, cooling, cleaning, maintenance, catering, etc.
  • Improved employee performance and reduction in absenteeism

Ultimately, the decision to assign a leader of remote work depends upon the benefits the organisation can realise from optimising the remote work experience for both the employees and the organisation, keeping remote and hybrid employees as productive and engaged as possible.