That said, Amandeep Shergill answers those questions from the inside. He is the Director of Talent Acquisition at Automattic. Automattic runs WordPress.com, WooCommerce, Tumblr, Simple Note, VaultPress, and other major platforms. Those products power more than 43 per cent of the internet. 

Amandeep began in agency recruitment, where both speed and care are essential. He later moved in-house and was hired by companies across blockchain, fintech, and fast tech sectors. He joined Automattic because it mixes profit, mission, and support for the open web. 

He leads hiring in a fully distributed company of about 1,500 people. They operate across 90 to 95 countries and don’t use traditional offices. They rely on trust, strong writing, and self-leadership to keep work moving. He also supports a flat structure and a strict trial-based hiring process.

In this article, you’ll see what shaped Amandeep’s path into talent leadership. You’ll learn how written-first work flows across time zones, day after day. You’ll also see why Automattic tests candidates with real trial projects. We’ll cover what Amandeep looks for during the trial, not just the final result.

We’ll explain how flat leadership works, and what “leads of leads” do. Additionally, we’ll examine coaching, training, and the habits that help individuals stay. By the end, you’ll know what makes distributed work feel calm, not chaotic.

How does someone like Amandeep reach this role, and what shapes the path?

Amandeep’s path into talent leadership starts in agency recruitment. Agency work moves fast and pushes you to judge people with care and speed. You deal with pressure, shift plans often, and still maintain stability. Moving in-house then gives her a closer view of how hiring shapes teams and long-term goals. She sees how every hiring choice changes how people work together.

Image Credits: Photo by Christina Morillo on Pexels

Her experience across blockchain, FinTech, and software adds a useful range. Each field has its own pace and style, so she learns to adjust her approach. 

This blend aligns well with Automattic, the company behind WordPress, WooCommerce, Tumblr, SimpleNote, and other tools that millions of people use daily. Automattic is profitable and also aims to support the open web, which gives the work a sense of purpose.

Working in a fully distributed company

Automattic runs as a fully distributed company. More than 1500 people work from over ninety countries without a central office. It sounds simple on paper, but it needs strong habits to run smoothly.

The structure works because of a few clear practices:

• Strong written communication supports most work.
• Minimal meetings keep focus high.
• Clear documentation enables teams to stay aligned across different time zones.
• Self-leadership sits at the core of each role.

Teams still meet in person at least once a year. Some teams meet more often when their work needs a deeper connection. These meetups help people build trust and gain a deeper understanding of each other.

How the work flows

Automattic follows a sun rhythm. Someone documents their work, hands it over, and a teammate in another country picks it up. It maintains steady progress without pushing people too hard. Teams typically consist of six to seven people and are often spread across different regions.

Why hiring works differently

A distributed structure requires a hiring process that evaluates actual skills and work style. Every candidate completes a trial project before joining Automattic. The project assesses whether someone can perform the job and work effectively in this asynchronous setup.

The final output matters, but the process says more. Amandeep looks at how people plan, ask questions, write updates, and manage uncertainty. Most people who don’t pass struggle with these softer skills. This careful filter protects the culture and keeps Automattic’s distributed model strong.

How a fully distributed company shapes support, leadership, and growth?

Distributed teams rely on self-driving and autonomy. People manage their own work without constant supervision. This setup works best for experienced professionals who can stay focused and organized. It can challenge people who like quick, in-person feedback. 

Teams in different time zones sometimes have hours with few members online. Early-career employees may struggle in this environment, so distributed companies usually hire mid-level and senior staff who can work independently.

Image Credits: Photo by Antoni Shkraba Studio on Pexels

Supporting team members

Strong support keeps distributed teams running smoothly:

• Clear written communication replaces most live calls
• Minimal meetings allow focus on actual work
• Optional in-person meetups build trust and connections
• Trial projects test output and collaboration skills

This setup ensures that people stay accountable, learn to manage themselves effectively, and communicate clearly.

Leadership in distributed environments

Leadership focuses on guidance, not control. Roles include leads and leads of leads. They help teams work well without adding unnecessary layers. 

The structure remains flat, allowing anyone to reach senior leaders directly. Leadership is open, accessible, and encourages collaboration at all levels.

Growth and training

Companies provide structured programs for new leads and leads of leads. Training includes:

• Managing conflict and difficult conversations
• Setting frameworks for team collaboration
• Understanding team dynamics, like forming and storming
• Attending sessions virtually or in person
• Access to internal learning, coaching, and books

All employees, regardless of their role, can access coaching. This ensures steady skill growth and support.

Retention and culture

Retention is higher than in typical tech companies. People stay long-term because the focus is on learning, openness, and meaningful work. 

Teams welcome flexible lifestyles if employees deliver quality work and care about the company’s mission. The emphasis is always on skill, contribution, and alignment with company values rather than office presence or perks.

Developing leaders in a fully distributed company

Developing leaders in a distributed setup needs careful attention. New leaders often step into complex problems fast, and they need time to learn without slowing their teams. 

That’s why companies try to strike a balance. They promote people who understand the culture, and they bring in outside leaders when they need fresh skills. When this mix works well, teams achieve stability and new ideas simultaneously.

Image Credits: Photo by Anna Shvets on Pexels

Structured spaces for reflection

Distributed teams rely on clear spaces where people can think, share ideas, and learn from one another. These usually include:

1. Leadership-focused Slack channels: These channels enable people to communicate openly, ask questions, and receive support when needed.
2. Internal blogging spaces: Leaders write about their experiences, share lessons, and learn from posts written by others.

These spaces maintain honest and steady communication. Moreover, they help leaders develop self-awareness, even when they work remotely from their teams.

Training programs for leadership growth

Leadership training stays practical and flexible. Programs focus on conflict resolution, team dynamics, and tough conversations. Sessions run online and in person, allowing people to choose what suits their schedule. 

Leaders also have access to coaching, internal courses, and books without strict limits. This support gives them the confidence to guide teams through everyday challenges and bigger shifts.

Scaling leadership with growth

Fast growth adds pressure, and teams can change quickly. Hiring may spike, and new leaders join at a rapid pace. That said, strong training and steady reflection spaces help people settle in and stay aligned. 

They learn how to handle their role, support their teams, and maintain a steady culture even when things move quickly.

With the right mix of internal growth, external hiring, shared spaces, and flexible training, distributed companies cultivate leaders who remain grounded, communicate effectively, and guide their teams with confidence.

Supporting leaders and attracting talent in a fully distributed company

Leading in a distributed company means working with constant movement. Teams grow, roles shift, and new people join often. That creates energy, but it also brings pressure and fatigue. Leaders need to keep one eye on the day-to-day and one eye on the bigger picture. 

They have to switch between details and direction many times in a week, and that switching takes real skill. That said, with the right support, it becomes a lot more manageable.

Image Credits: Photo by Christina Morillo on Pexels

Coaching as steady support

Coaching provides leaders with a space to pause and think clearly. They can discuss challenging situations, test ideas, and reflect on their own behaviour. A good coach doesn’t tell them what to do. 

Instead, the coach asks strong questions and helps them see patterns. This support matters greatly when teams are changing rapidly and expectations are continually rising.

Recruitment challenges that shape hiring

Recruitment looks busy from the outside, but it’s messy inside. Companies receive a large number of applications, yet many are:

• AI-generated or copied
• Not honest about skills or experience
• Unclear fits for the open role

Because of this, recruitment teams don’t just sit and wait. They actively search, reach out, and build pools of people who align with the work and culture. This approach takes more effort, but it clearly improves quality.

Human-centric benefits that improve retention

Benefits send a strong signal about what a company values. Pay parity, generous leave, sabbaticals, and support for home office setups all show respect for people’s lives. 

Coaching for everyone, not just senior staff, adds to that message. People feel seen as individuals, not just as data points.

Culture rooted in a community mindset

A distributed company works best when people care about more than their own success. When the culture borrows from open-source thinking, it encourages sharing, openness, and a sense of community. 

People want their work to lift others, not just themselves. That mindset holds the whole system together, even when no one shares the same office.

Conclusion

A fully distributed company can run fast and stay stable, but only with the right habits. Automattic shows what those habits look like in real life. 

Teams write things down, keep meetings low, and use clear docs to stay aligned. They also meet in person at least once a year, as trust still requires time spent together.

Hiring also changes in this setup. Amandeep doesn’t just look at a polished resume or a strong interview. She tests real work through trial projects. 

She watches how people plan, ask questions, share updates, and handle unclear moments. That filter protects the culture and keeps daily work smooth across time zones.

Leadership works differently, too. Leads guide instead of control, and the structure stays flat and open. Coaching and training then help people grow without burning out. 

Add fair benefits and a mission people believe in, and retention gets stronger. In short, distributed work doesn’t win through perks. It wins through trust, writing, and steady people practices.

FAQs

How does a fully distributed company handle time zone gaps without slowing work?

A fully distributed company plans work around handoffs. People document progress clearly and pass tasks forward. That keeps momentum steady, even when hours do not overlap.

Does a fully distributed company reduce chances for career visibility?

A fully distributed company values written impact, not visibility. Clear updates and shared results make work visible. People earn recognition through their contributions, not their presence.

How does a fully distributed company manage poor communication habits?

A fully distributed company establishes clear writing standards from the outset. Leaders give direct feedback on unclear updates. Over time, communication quality improves through practice and examples.

Can a fully distributed company effectively support junior employees?

A fully distributed company can support juniors, but it requires a significant amount of effort. Clear docs, mentoring, and structured feedback matter. Many teams still prefer experienced hires for smoother flow.

How does a fully distributed company prevent burnout?

A fully distributed company encourages flexible schedules and fewer meetings. People control their pace and focus. That freedom reduces constant pressure and context switching.