In 2022, I joined a small group of leaders with a shared mission. Our job titles were usually some variation on “Director of Remote Work” (at Upwork, I was Director of Remote Org Effectiveness) and our role was to help our respective companies thrive in a digital-first environment. However, as futurists, most of us also knew this role wouldn’t stay the same forever. Even as we embraced the task at hand, we acknowledged our jobs were destined to evolve and change.
In 2025, the “Head of Remote” job is indeed morphing into something new. Companies aren’t looking for a single person with a singular focus on remote ops; we’re entering a new era of workplace management that integrates operations with culture, aligning the “how” of remote work with the “why.”
Meanwhile, the “return to office” trend is in full swing — for now. But don’t be fooled: companies will continue to incorporate flexible, hybrid, and even fully remote models, and a remote-first approach will continue to be a competitive advantage. The next few years will see a shift in leadership attitudes and a massive upskilling of workforces, making distributed work far more effective and widespread.
And while the “Head of Remote” trend may not return in exactly the same form, there will be a growing need for leaders with remote operations experience.
The rise of the ‘Head of Remote’ role
The first “Head of Remote” role was created at GitLab in 2019. I joined that remote work thought leadership team in 2020, just as the pandemic was threatening to shut down the world.
Once lockdowns flipped workplaces inside out, businesses that had never operated remotely suddenly needed a dedicated leader to establish policies, integrate collaboration tools, and foster company culture in a digital-first environment. “Head of Remote” was touted as tech’s hottest job in 2021. Throughout the industry, operations experts popped up to tackle the thorniest challenges in transitioning to remote work, like:
- Policy Development: Creating guidelines for remote work operations.
- Technology Integration: Ensuring employees had the right tools and software.
- Culture & Engagement: Building a strong company culture despite physical distance.
- Collaboration & Productivity: Streamlining communication and workflow efficiency.
The “head of remote” class of 2020-2022 included Darren Murph at GitLab; Annie Dean at Facebook; Allison Vendt at Dropbox; and several others. As remote work leaders, we solved an urgent need for our companies: rapid transition to digital operations and the establishment of a baseline of best practices. My role at Upwork involved upgrading both systems and behaviors: establishing the philosophy, ability, and expectation for working digital-first.
But even with these foundational elements in place, the journey is really only beginning. Change management — the process of transforming a company’s mindset and habits — is a much longer-term project, and it requires participation from the entire team.
Why companies are moving away from ‘Head of Remote’
Five years after the lockdowns, remote work is well-established, but many workplaces aren’t much closer to solving its challenges: communication issues, meeting overload, and faltering engagement, to name a few.
The factors blocking effective remote work are fairly consistent across companies, and they can be generalized into two buckets:
1 – Remote ops struggle because digital-first best practices aren’t fully integrated into every process, system, and human interaction.
2 – Many workers (and leaders) think they know how to be effective while working remotely, but their only real experience is “pandemic remote.”
Effective remote work takes time to develop. GitLab was founded in 2014, and gained prominence for its remote ops 6 years later. Even those of us who’ve been working remotely for decades will admit we only mastered it after 5-10 years of hands-on experience.
It takes time because distributed work must be an integrated practice. In other words, you can’t just tell everyone how to work remotely; you need to iterate on every piece of the company and train every individual.
Smart organizations are recognizing that a siloed “Head of Remote” with a 2-year strategic plan isn’t able to accomplish all this; instead, they’re distributing the work of change management throughout the company, and embedding it into a wide range of leadership roles.
Digital-first becomes part of a broader strategy
The majority of companies are now working in a hybrid capacity, blending in-office and remote setups. Whether the company requires three days in the office, or whether some people are onsite while others are remote, most organizations now expect that work happens on digital tools and platforms, and that meetings will often be virtual.
An integrated digital transformation is underway at even the most traditional firms, increasing agility and flexibility without sacrificing effective work. For example:
- People/HR teams now oversee remote work practices alongside general workforce management, culture building, and employee experience.
- IT departments manage collaboration tools and cybersecurity for both in-office and remote employees.
- Operations and Workplace teams handle office logistics, support in-person events, and provide remote workplace support.
As a general rule, these are separate functions that are more effective when working tactically on the most timely issues in their own spheres. A top-down plan could be overly constricting, limiting their ability to accomplish a transformation.
Remote work strategy then becomes an executive-level initiative, passed down as strategic objectives. You might see a COO or a Chief of Staff setting priorities or focus areas, rather than an internal consultant advising on implementation.
Shifting focus to experience and growth
As I mentioned, we still face a big challenge: most people haven’t actually worked remotely at scale, or over a longer period of time, or outside the confines of a pandemic.
I recently did an AMA with the Running Remote community, where I was asked questions like:
- How do you measure remote effectiveness?
- How do you build culture without in-person events?
- How do you hold people accountable for remote best practices?
We’re now seeing the rise of a new group of leaders at remote-first companies, who are tasked less with the basics of remote operations, and more with the second-order challenges of effectiveness, collaboration, culture, growth, and people development. A few of the roles I’ve seen taking on this work:
- Head of Workplace Experience: Focuses on employee well-being, engagement, and digital workspace optimization.
- People & Culture Lead: Ensures strong company culture, onboarding, and team cohesion.
- Talent Development / Learning Leader: Prioritizes career growth, professional development, and leadership training in a distributed workforce.
- Head of Organizational Development: Tracks implementation, productivity, work management, and strategy.
All of these roles build on a foundation of best practices, but they shift and evolve the focus to develop what the company needs most: people-centric leadership, better collaboration and communication, and a way to track consistent, measurable progress toward long-term success.
Future casting: how “return to office” will be the next trend to die out
Many of my fellow future-of-work experts have been stunned at the parade of companies announcing that they’re calling their teams back to the office. This very unpopular trend is championed primarily by executives, and resented by workers. Like a wave crashing on a beach, the RTO trend will soon pass as attitudes and priorities equalize over time. Here’s what I think is really going on:
Offices are expensive, but most companies have long-term leases (or outright purchases) for their office space. It’s a big outlay, but it’s not one they can easily cut off. This doesn’t mean they aren’t strategizing to reduce real estate costs.
Larger or more traditional companies are smart to recognize that a digital transformation will take them more time. This doesn’t mean they aren’t working on it.
Flexible, hybrid, or fully remote work is a huge attractor of high-skilled talent. Companies that want to stay competitive will be working on a strategy to provide flexibility and reduce overhead. In other words, they will find a way to move to a hybrid or remote model.
I have every reason to believe that many of the companies who’ve recently “RTO’ed” have secret teams working on their transition plan to get away from their offices. Behind the scenes, their digital transformations are very much underway, and their strategists and analysts are working hard on planning for effective distributed operations.
Wouldn’t you be doing the same?
Check back with me in five years.
I could be wrong, but here’s my prediction: by 2030, hybrid work will be the norm and remote work will be widely accepted. There will be a general consensus of how remote operations work at a foundational level, with many different models of implementation from one company and industry to another. All this will be led by workplace leaders with hands-on experience and training in remote operations, but the operational knowledge of how to manage a remote team will be widespread — because it’ll be considered a must-have for manager training.
Let me know in five years how I did with that prediction. Until then, refer to my guide to what the best remote and hybrid companies are doing right.
