Alternative Leadership Series: The Digital Nomad Manager

Three years managing AI teams from an ironing board. Leadership, trade-offs, and knowing when to stop

Gilad’s Note: I'm launching a new series exploring how tech leaders are redefining what career success looks like. First up: Yaron Gurovich, Head of AI Research and Applications at Vimeo, who spent three years leading teams while traveling the world with his family. Here's his story, in his own words.

Three Years, 15+ Countries, One AI Team

How I led machine learning teams at Vimeo while living as a digital nomad - and what I learned about leadership, trade-offs, and knowing when to stop

It's 2 AM in Vietnam.

My family is asleep in the next room while I'm debugging product strategy with my team in New York. The ironing board I've converted into a standing desk creaks under my laptop's weight.

This isn't desperation. It's intentional design.

For three years, I managed AI teams at Vimeo while traveling the world with my wife and kids. What started as a pandemic experiment became a crash course in remote leadership, family dynamics, and the real cost of unconventional choices.

Here's what I learned.

The Foundation Nobody Talks About

Let me start with the truth that nobody mentions about nomadic leadership.

Your partner has to be all in.

Not supportive. Not understanding. All in.

This only works if both people are fully engaged in the process. It's a true partnership. While I focused on maintaining my role at Vimeo, my wife handled everything else - finding schools, building social circles, managing logistics.

Without that foundation? You're building on quicksand.

We learned this the hard way during our first few months. The romantic notion of "working from anywhere" crashes into reality pretty quickly when you're trying to join a crucial product meeting while your kids are melting down because they can't find their favorite toy in yet another new apartment.

The partnership had to be rock solid. Regular check-ins. Honest conversations about what was and wasn't working. Space for either of us to say "this isn't sustainable" without judgment.

Building Trust From an Ironing Board

Our setup in Greece was ridiculous.

Every apartment had ironing boards, but no one had proper desks. So I turned that ironing board into my workstation - height-adjustable, portable, and surprisingly stable.

I spent months working from that setup. Video calls with senior leadership. Technical deep-dives with my engineering team. Product strategy sessions.

The results? My team started saying I was more available than anyone else in the company.

Here's the counterintuitive part: being nomadic made me a better remote manager.

When you're constantly adapting to new environments, you get really good at the fundamentals. Communication becomes crisp. Planning becomes essential. Trust becomes everything.

I structured my days around three time zones:

• Morning: Deep focus work (my time) and collaboration with my teams in Ukraine and Israel. 

• Midday: Family time and local experiences

• Evening: US team collaboration

The timezone challenges forced me to be more intentional. In Israel, working with the US team meant late nights. In Southeast Asia, it meant really late nights - sometimes until 2 AM.

But I made a commitment: nothing would be blocked waiting for me. Ever.

If someone needed a decision, they got it. If there was a crisis, I was available. My team knew they could reach me at any hour, any timezone.

That consistency built trust in ways I never expected.

Staying Technical Without Writing Code

Here's where most engineering managers get it wrong.

They think staying technical means writing code.

I disagree.

A technical manager needs to have deep conversations with their team about trade-offs. About how to approach problems. About breaking down complex challenges. That doesn't require writing production code.

My approach to staying current:

• Build small POCs to understand new technologies

• Have deep technical discussions with my team during reviews

• Research emerging patterns when gaps appear in my knowledge

When AI agents started changing software development, I didn't panic about falling behind. I dove into research, built test projects, had long discussions with my engineers about implementation approaches.

The key insight? Technical leadership is about intuition, not implementation.

You need to understand how technologies behave. Where they excel. Where they break. How they fit together.

But you don't need to be the one building them in production.

When the Honeymoon Ends

After three years of nomadic family life, something shifted.

The constant novelty stopped feeling novel. The trade-offs started weighing heavier. Building relationships became harder when everything was temporary.

There's this fuel that drives the adventure. But it eventually runs out.

You reach a decision point - either adapt your life to make this sustainable long-term, or transition back to a more traditional setup.

The kids wanted stability. Real friendships. Consistent schools. Ability to invest in advanced classes which lack online presence.

My wife and I wanted to build deeper community connections instead of constantly starting over.

We chose to settle. Not because the nomadic life failed, but because we had extracted what we needed from it. 

The Real Trade-offs

Three years of nomadic leadership revealed trade-offs I didn't expect:

Flexibility vs. Stability: Constant adaptation builds resilience but makes deep local relationship-building harder.

Availability vs. Boundaries: Being reachable across all timezones builds trust but demands personal sacrifice.

Adventure vs. Routine: Novel experiences energize initially but become exhausting after a while, when the Adventure is becoming your routine, it may be a time to change it.

Individual vs. Family: What works for one person doesn't automatically work for everyone. For a family of 5 that is constantly moving, this means a lot of attention to the individual needs.

None of these trade-offs are inherently right or wrong. They're choices.

The mistake is pretending they don't exist.

What I'd Tell Someone Starting

If you're considering a similar path, here's my advice:

Start with partnership. Both partners need to be genuinely excited about this experiment. One person dragging the other along is a recipe for resentment.

Plan for the transition periods. Moving every few weeks is exhausting. We learned to stay 2-3 months minimum in each place. Some families we met had been doing this for years - they stayed 6+ months per location.

Understand your work constraints. I could do this because Vimeo already had a strong remote culture. If your company expects face time, this becomes much harder.

Recognize when it's time to evolve. Not every experiment needs to become permanent. Extract the learning and make the next decision.

Embrace Temporality: I learned that decisions become easier when you know they're temporary. For example, it's simpler to choose an apartment from a distance when you're only renting for two months.

The Unexpected Outcome

Here's what surprised me most about three years of nomadic leadership.

It wasn't the exotic locations or Instagram-worthy moments.

It was discovering what actually mattered.

Stripped of familiar routines and support systems, you learn what's essential. For leadership, for relationships, for life.

The fundamentals become crystal clear: trust, communication, intentionality.

Everything else is just location.

Yaron Gurovich is Head of AI Research and Applications at Vimeo, where he leads teams building machine learning solutions for video platforms. He holds an MSc in Electrical Engineering from Tel Aviv University and has published research in computer vision and AI applications in healthcare. You can follow his travels @journey.gurovich.