Head of Remote
Quick Start Guide
Your guide to building a remote-first organization
Empower your organization to work anywhere
and achieve its goals everywhere
Whether stepping into a new Head of Remote role, improving your existing strategy, or leading a company through a flexible work transformation, this guide has actionable insights tailored for you.
Struggling to make remote work… work?
“Productivity is down. We’re not seeing progress.”
→ Leaders often struggle to “see” people working in a remote environment, leading to doubts about productivity. Shifting from time-based to results-based measurement provides clarity and trust. By focusing on outcomes, creating systems that make work visible, and aligning expectations, you can ensure progress is measurable and deliverable—no matter where your team is
“People are disappearing.”
→ Remote work can feel isolating when there’s no visibility into what people are doing or how they feel. Learn how to recreate “presence and context” online so team members feel seen, heard, and connected — no matter where they are.
“There is less social connection.”
→ In a remote-first environment, strong work relationships are built intentionally—often asynchronously—through clear communication, shared goals, and meaningful interactions. While friendships may form naturally, the focus is on creating a sense of belonging and connection to the team’s purpose. By designing opportunities for collaboration, recognition, and shared achievements, leaders create the conditions for individuals to thrive and deliver value together.
“Cross-team collaboration feels weak.”
→ While individual teams may thrive, broader collaboration across functions often suffers. Learn how to give teams a reason to connect, organize functional groups (like Communities of Practice), and break down silos that slow progress and innovation.
These challenges are real, but they’re solvable. With proven solutions, expert insights, and actionable advice from the Head of Remote Quick Start Guide, you’ll create an organization where productivity thrives, people feel connected, and results speak for themselves.
Download your guide and start transforming your workplace today.
Key benefits and what’s inside the guide
New Heads of Remote: Gain a clear roadmap for the first 90 days and beyond - from building operational systems to nurturing team culture.
Company Leadership: Understand the strategic value of remote work and discover how to implement and measure its success.
HR Professionals: Identify the skills, tools, and responsibilities needed to support or hire for the Head of Remote role.
Transitioning Organizations: Build strong foundations for remote work with practical tools, frameworks, and case studies.
Meet The Future of Work Expert Contributors
CHASE WARRINGTON
Head of Operations
DOIST
CHRIS DYER
Remote Work/Culture Expert
CLIFF POLLAN
CEO, Spatial Work Expert
WELO
GRAYSON HARRIS
Flexible Work Expert
NEI ELECTRIC POWER ENG
“After the pandemic forced many companies into remote work, most didn’t fully experience its benefits because they simply replicated their office environment online.
Now, with the rise of return-to-office mandates, I can’t help but wonder if things would have been different if companies had been better equipped to build functional remote environments.”
DAJANA B. ĐAKONOVIĆ
Head of People
TOGGL
JENNY VEGA
Performance Coach
SHINING VALLEY COACHING
JOANNE BARNETT
Founder
REMOTE WAYS OF WORKING
LAUREL FARRER
Org Development Expert &
Behavior Pioneer
LISETTE SUTHERLAND
Fractional Head of Remote
COLLABORATION SUPERPOWERS
KENNETH HELLEM
Chief People Officer
ULTIMATE BEAUTY
“The way we work is broken, and I truly believe there is a better way. Remote work, when done right, allows people to adapt their work to their life, increasing happiness, wellbeing, productivity, and results.”
MADISON CRANE
Head of Remote
THE REMOTE COMPANY
MICHAŁ PARKOLA
Manager, Speaker &
Leadership Mentor
MICHAEL FRAIDENBURG
Owner
THE COOPERATION COMPANY
NIKOLETTA TATÁR
Agile Coach &
Certified Scrum Professional
“The Head of Remote becomes your efficiency hack as an organization, driving the future of work and elevating productivity in a distributed environment.”
NADIA VATALIDIS
Director of Talent Acquisition
CARMUNDA
PETER MISCOVICH
Global Future of Work
Transformation Leader
ROWENA HENNIGAN
Head of Remote
NOSANA
SUSANNE HARELIUS
Jira Ninja, Atlassian Expert,
Engineering Manager
WAYNE TURMEL
Author, Trainer, Coach
KEVIN EIKENBERRY GROUP
VALENTINA THÖRNER
Head of Product Excellence
SCALAR at ZF
“There are a lot of strategies and tools out there to become a better remote worker, a better remote manager. It’s time we give the same focus to changing organizational structures, making compelling business cases, and facilitating remote work at scale.”
Get everyone’s knowledge in the guide
Listen to the Head of
Remote Podcast
The Head of Remote Podcast explores the emerging role of the Head of Remote, featuring insights and stories from pioneers shaping the future of work. Hear from leaders at companies like Toggl, GitLab, and Doist.
Each episode explores strategies for building connected, remote-first workplaces, from creating remote-first cultures to navigating tools, processes, and leadership challenges.
Who the Head of Remote guide is for:
This guide was designed with you in mind, no matter where you are on your remote work journey. Whether you’re a seasoned professional or just starting to explore the world of flexible work, you’ll find actionable insights tailored to your needs.
- Are you a new Head of Remote? Stepping into this role can feel like navigating uncharted territory. This guide provides a structured roadmap to help you excel in your first 90 days and beyond, setting the foundation for long-term success.
- Already a Head of Remote? Even the most experienced leaders need inspiration and fresh ideas. Discover ways to refine your strategies, tackle emerging challenges, and elevate your organization’s remote work game.
- Leading a company? As a CEO, COO, or founder, you know the importance of strategic investments. This guide will help you understand the Head of Remote role and make the case for why every remote-first organization needs one.
- In Human Resources? If you’re responsible for hiring and supporting remote work leaders, this guide offers insights into the skills, responsibilities, and tools that make a Head of Remote indispensable.
- Is your organization transitioning to remote or hybrid work? Whether you’re just starting or refining your processes, this guide provides practical steps to implement flexible work practices that drive results.
- Passionate about remote work? Even if you’re not in a leadership role, this guide will deepen your understanding of how remote processes work and how to champion flexibility in your workplace.
Get inspired with this guide
How this guide came together
What started as a simple checklist quickly evolved into a collaborative project driven by the collective expertise of remote work pioneers. Initially created to organize insights for the Head of Remote role, the checklist expanded as interviews with remote work experts revealed new strategies, practices, and challenges.
Recognizing the potential for this resource to benefit others, the checklist was opened to the global remote work community. To our delight, 20 contributors from around the world added their knowledge, refining and enriching the content.
We never sat around a conference table or worked from the same time zone. Instead, we used the very tools and practices this guide advocates—collaborative documents, asynchronous communication, and shared purpose—to create something we’re all proud of. This guide is more than a collection of advice; it’s a testament to the power of global collaboration and proof that remote-first principles work.