Crossover Logo
Log in
  • About
    About Crossover About Crossover

    Crossover is a global recruitment company that specializes in full-time remote jobs with AI-first tech companies. We enable the top 1% of global talent to qualify...

    Companies Hiring Companies Hiring

    Some of the 70+ companies that use Crossover to recruit global talent for high-paying remote positions.

    Reviews Reviews

    Hear testimonials from some of the 5,000+ rockstars who have found a rewarding career through Crossover.

    What is WorkSmart? What is WorkSmart?

    WorkSmart is Crossover’s internal productivity monitoring tool. It helps our elite remote workers stay focused, track their time, and get paid fairly - with real-time AI...

    About

    The world's largest database of skilled remote talent

  • For Jobseekers
    Current Job Openings Current Job Openings

    Crossover matches world-class people with world-class jobs at silicon valley software and EdTech companies. Earn USD from anywhere with a full-time remote job.

    Selection Process Selection Process

    Want to qualify for awesome remote jobs? Here’s what to expect from Crossover's AI-powered system of skill assessments.

    High-Paying Remote Jobs High-Paying Remote Jobs

    Find top remote jobs that pay you what you’re worth. Browse 70+ fully remote roles that match your skills, accelerate your growth, and give you the...

    US Education Jobs US Education Jobs

    Are your big ideas too cool for school? Join Crossover to qualify for the world's most innovative (and well-paid) jobs in education technology. Work full-time...

    For Jobseekers

    The world's best remote full-time jobs, with AI-first US tech companies

  • For Companies
    Hire on Crossover Hire on Crossover

    Forget average. Use our AI-powered smart filters to tap into the world's largest database of extraordinary remote talent.

    How to Hire Global Talent How to Hire Global Talent

    Need a smarter way to shortlist global contractors? We’ve spent 10 years perfecting a process that eliminates barriers, guarantees outstanding matches, and saves you time-to-fill.

    How to Manage Distributed Teams How to Manage Distributed Teams

    Streamline everything from contracts and payroll to productivity management.

    Remote Software Developers Remote Software Developers

    Find and hire the top 1% of remote software developers in the world through Crossover. Tap into a global talent pool of 7 million rigorously tested...

    For Companies

    Get the world's best AI experts on your team, in 5 mins a day

  • Reviews
  • Resources
  • Help
Crossover Logo
🔓 Unlocking the ultimate AI playbook for remote workers ft. Iwo Szapar | Ep66 OoO

Share

  1. Home
  2. Resources
  3. Out of Office
Out of Office

🔓 Unlocking the ultimate AI playbook for remote workers ft. Iwo Szapar | Ep66 OoO

Andrew Allen by Andrew Allen
  VP of Content Marketing
🔓 Unlocking the ultimate AI playbook for remote workers ft. Iwo Szapar | Ep66 OoO
Contents
  • Hey, Welcome Back!
  • Featured Guest
  • You Might Have Missed…

Ai is impacting remote work in a BIG way. But how? This week's guest chats to Andrew about transforming underperforming distributed teams into powerhouses of productivity and happiness.

Hey, Welcome Back!

Can you really be happier, healthier AND more productive?

Up until recently, no one would have dared mix these three elements with remote work, especially not remote-averse CEOs.

But times are changing. Not too long ago, grueling hours and brutal adjustment periods were the norm for many distributed teams.

🦾 Remote work pioneer Iwo Szapar says: those days are gone thanks to AI!

Co-founder of Remote-how and the Remote-First Institute, Iwo has worked with Microsoft, ING Bank and Walmart – and penned an industry manifesto called ‘Remote Work is The Way.’

Along with living in 15 different countries, Iwo has been featured in Forbes and BBC for his trailblazing insights and hands-on work in the remote space.

His latest mission? Exploring the massive impact of AI on remote work.

I caught up with Iwo to uncover the research he's been doing to flip outdated assumptions about remote work productivity on its head.

😇 It turns out, AI and remote work are a match made in heaven…despite the ongoing battles raging in the tech world.

Artificial intelligence can make distributed teams happier and more efficient. Whether you're in different cities or on different continents, AI enables you to tap into global opportunities.

Bad team management has given remote work a bad rap.

Iwo joins me this week to dig into how AI can help companies who are (frankly) bad at remote management.

✅️ The first step is realizing where the REAL problem lies!

✅️ Avoid the panicked office return and fix the core issue instead

✅️ Overhaul the people and processes that aren’t working

The industry LOVES to blame poorly performing remote teams on remote work itself. But now companies can harness the power of AI to radically transform how teams operate online.

Lucky for us, Iwo has walked many teams through this transformation process.

AI is here to empower individuals to work smarter, not harder, and to help organizations establish healthy workflows and processes.

Who wouldn’t want their global team to achieve more in a day?

Imagine having tools that not only accelerate results but also boost happiness – that’s the magic of AI.

Remote work automation is supercharged with AI.

📈 Take Productivity Partner, for instance – Iwo’s innovative AI assistant.

It helps remote workers plan their day, acts as a personal productivity coach, and provides real-time feedback.

This assistant keeps workers on track, inspires improvement, and offers the daily support needed to feel genuinely happy.

AI can check in on your team for you, replacing clunky methods like surveys!

In episode 66, Iwo and I get to the nitty-gritty of integrating AI into your distributed team. We're talking about transforming underperforming teams into powerhouses of happiness and productivity.

Remote work is leaving the office in the dust. And now with AI, it’s only going to get smarter, faster and easier for remote workers.

😱 Imagine when it’s 10X better – 100X better. 😱

Are you ready to embrace the win-win of the century?

Then watch this week’s episode so that you don’t get left behind.

📽️ This Week on Episode 66:

🗣️ Facts Over Opinions: Discover how AI will make remote workers happier

🧘 Team Wellbeing: Learn how AI can significantly boost your team's wellbeing

👾 Productivity Coaches: See how AI assistants transform remote team culture

🌟 Iwo’s STEP Framework: Get a powerful framework to upskill & reskill like a pro

🧐 Work Smarter, Not Harder: Iwo's philosophy of leveraging AI for smarter work

A huge thank you to Iwo Szapar for joining me on the show. Your insights and experiences are invaluable to the companies, remote workers and leaders in our community.

It’s time to revolutionize your remote work experience.

Tune into this week’s episode for a crash course on how AI can make your distributed team smarter, faster, and happier every single day.

🤖 Enjoy!

The future is office-optional,

Andrew

Featured Guest

Image

Iwo Szapar is CEO of Remote-how and co-founder of the Remote-First Institute, and is a leading remote work advocate. Since 2017, he's helped 3000+ companies, including Walmart and Microsoft, optimize their distributed teams.

Featured in Forbes, BBC, and Business Insider, Iwo is also the author of Remote Work Is the Way. A passionate traveler, he's lived in 15 countries over five years.

Follow him on LinkedIn, X and Instagram.

You Might Have Missed…

▶️ The Real Reason Remote Work Makes You Happier

▶️ 7 Unconventional Remote Work Podcasts That Deserve Your Attention

▶️ Are You Cut Out for Crossover? Traits We Love That Get You Hired

▶️ 7 Global Talent Trends in international Hiring

🤩 The latest Radically Remote: The Happiness Heist Edition

🚨 Hiring the top 1% talent in the world? Here they are.

🎥 Guest star on Out of Office! Apply here!

Similar post
📢 Breaking news: The FINAL episode of Out of Office with Andrew Allen | Ep84 OoO

Hey, Welcome Back! One. Last. Time. You probably thought I’d keep going forever, likeMarvel spin-offsor awkwardZoom meetings that should’ve been emai...

Read more
Out of Office Logo
PODCAST SERIES
Out of Office
The least boring remote work news source on the planet. Meet expert and ordinary remote workers from around the world.
View All Episodes

Share

Andrew Allen
ABOUT THE AUTHOR

Andrew Allen

  VP of Content Marketing

Andrew lives in Auckland, New Zealand and has worked full-time remotely for Crossover since early 2021. His superpower is using storytelling and humor to make interesting and memorable insights on complex topics. He's known for hosting the world's most-viewed remote work vlog (Out of Office), co-creating one of the most-subscribed newsletters on LinkedIn (Radically Remote), and contributing to Forbes. Beyond work, Andrew has visited over 100 countries, seen all seven wonders, and starred in a few high profile TV shows and musicals in New Zealand. You can hear a bit more of his backstory (and meet his dogs) here.

Return to Top
Read Next
🛺 A call to remote leadership with Rahul Subramaniam | Destination India Part 1 OoO

Blog

View all blogs

Want to read more?
We have a lot more where that came from

The Future of Work
How to Stop Social Offloading from Hijacking Your Remote Team
Ever used AI to respond to a team email, DM or give feedback on a key project? Everyone’s doing it these days. Companies have been falling o...
Read more
How to Stop Social Offloading from Hijacking Your Remote Team
The Future of Work
Why Worker-Built Shadow Apps Need Better Remote Leadership
AI has made every remote worker a halfway decent coder. But what happens when leaders realize they have swarms of apps, automations and work...
Read more
Why Worker-Built Shadow Apps Need Better Remote Leadership
The Future of Work
Why Never Do Unpaid Work Is Bad Career Advice
Never work for free. It’s a catchy slogan we can all get behind, and one a lot of people on the internet have embraced lately. Everyone dese...
Read more
Why Never Do Unpaid Work Is Bad Career Advice
The Way We Work
5 Habits That Make Remote Contract Work Truly Elite
Elite remote contract work is a build, and the blueprint is far more repeatable than most contractors realize. A lot of people explain away ...
Read more
5 Habits That Make Remote Contract Work Truly Elite
The Future of Work
How to Manage AI Agents Without Wasting Time or Tokens
AI agents have changed the economics of work. One superagent operator can literally run an entire company from a laptop. That single skilled...
Read more
How to Manage AI Agents Without Wasting Time or Tokens
The Future of Work
Why Autonomous AI Needs Autonomous People First
You’ve been given a mandate at work - excel with autonomous AI. The only problem is that no matter how much you learn, automate or build… yo...
Read more
Why Autonomous AI Needs Autonomous People First
The Future of Work
Top 100 Companies to Watch for Fully Remote Jobs (Part 2)
The smartest companies to watch for remote jobs are often found in the markets most job seekers overlook. Everyone watches the obvious names...
Read more
Top 100 Companies to Watch for Fully Remote Jobs (Part 2)
The Future of Work
Top 100 Companies to Watch for Fully Remote Jobs (Part 1)
Finding the right companies to watch for remote jobs is not about chasing every employer with 'remote' in the job description. Plenty of com...
Read more
Top 100 Companies to Watch for Fully Remote Jobs (Part 1)
The Way We Work
12 Best Digital Nomad Jobs in 2026
Forget the beach-bum-with-a-laptop cliché - the best digital nomad jobs in 2026 are professional careers you can pursue full time, with real...
Read more
12 Best Digital Nomad Jobs in 2026
How to Crossover
Crossover’s Basic Fit Check [Official AI Screening Guide]
Are you fit for the role you’re applying for? We get it – our jobs are flexible, AI-forward and highly paid. Who wouldn’t want to apply to a...
Read more
Crossover’s Basic Fit Check [Official AI Screening Guide]
The Future of Work
How to Beat AI Brain Fry
Pick, stitch, swap, insert, edit, tweak, reorganize. If you spend your days building with AI or directing a litany of models and tools, you ...
Read more
How to Beat AI Brain Fry
Building a Remote Workforce
3 Ways Remote Work Innovation Improves In-Person Work
Most people make the mistake of thinking remote work is ONLY about where you work. But they're missing the real workplace update happening r...
Read more
3 Ways Remote Work Innovation Improves In-Person Work
Achieving Excellence
7 Flexible Remote Work Hacks for Time-Poor Workers
Flexible remote work handed you back 3 precious hours from your old soul-crushing commute. But your days still feel like they're running on ...
Read more
7 Flexible Remote Work Hacks for Time-Poor Workers
The Future of Work
How Remote Work Unlocks AI Superusers with Darren Murph
Darren Murph helped define the first era of distributed work. As GitLab’s Head of Remote (and the first person ever given that title), autho...
Read more
How Remote Work Unlocks AI Superusers with Darren Murph
The Future of Work
How to Build Real Expertise When AI Does the Grunt Work
Your Zone of Genius has a training problem. So does mine. It’s true, AI can make you look more capable before it makes you more capable. It’...
Read more
How to Build Real Expertise When AI Does the Grunt Work
The Future of Work
How to Stop Social Offloading from Hijacking Your Remote Team
Ever used AI to respond to a team email, DM or give feedback on a key project? Everyone’s doing it these days. Companies have been falling o...
Read more
How to Stop Social Offloading from Hijacking Your Remote Team
The Future of Work
Why Worker-Built Shadow Apps Need Better Remote Leadership
AI has made every remote worker a halfway decent coder. But what happens when leaders realize they have swarms of apps, automations and work...
Read more
Why Worker-Built Shadow Apps Need Better Remote Leadership
The Future of Work
Why Never Do Unpaid Work Is Bad Career Advice
Never work for free. It’s a catchy slogan we can all get behind, and one a lot of people on the internet have embraced lately. Everyone dese...
Read more
Why Never Do Unpaid Work Is Bad Career Advice
The Way We Work
5 Habits That Make Remote Contract Work Truly Elite
Elite remote contract work is a build, and the blueprint is far more repeatable than most contractors realize. A lot of people explain away ...
Read more
5 Habits That Make Remote Contract Work Truly Elite
The Future of Work
How to Manage AI Agents Without Wasting Time or Tokens
AI agents have changed the economics of work. One superagent operator can literally run an entire company from a laptop. That single skilled...
Read more
How to Manage AI Agents Without Wasting Time or Tokens
The Future of Work
Why Autonomous AI Needs Autonomous People First
You’ve been given a mandate at work - excel with autonomous AI. The only problem is that no matter how much you learn, automate or build… yo...
Read more
Why Autonomous AI Needs Autonomous People First
The Future of Work
Top 100 Companies to Watch for Fully Remote Jobs (Part 2)
The smartest companies to watch for remote jobs are often found in the markets most job seekers overlook. Everyone watches the obvious names...
Read more
Top 100 Companies to Watch for Fully Remote Jobs (Part 2)
The Future of Work
Top 100 Companies to Watch for Fully Remote Jobs (Part 1)
Finding the right companies to watch for remote jobs is not about chasing every employer with 'remote' in the job description. Plenty of com...
Read more
Top 100 Companies to Watch for Fully Remote Jobs (Part 1)
The Way We Work
12 Best Digital Nomad Jobs in 2026
Forget the beach-bum-with-a-laptop cliché - the best digital nomad jobs in 2026 are professional careers you can pursue full time, with real...
Read more
12 Best Digital Nomad Jobs in 2026
How to Crossover
Crossover’s Basic Fit Check [Official AI Screening Guide]
Are you fit for the role you’re applying for? We get it – our jobs are flexible, AI-forward and highly paid. Who wouldn’t want to apply to a...
Read more
Crossover’s Basic Fit Check [Official AI Screening Guide]
The Future of Work
How to Beat AI Brain Fry
Pick, stitch, swap, insert, edit, tweak, reorganize. If you spend your days building with AI or directing a litany of models and tools, you ...
Read more
How to Beat AI Brain Fry
Building a Remote Workforce
3 Ways Remote Work Innovation Improves In-Person Work
Most people make the mistake of thinking remote work is ONLY about where you work. But they're missing the real workplace update happening r...
Read more
3 Ways Remote Work Innovation Improves In-Person Work
Achieving Excellence
7 Flexible Remote Work Hacks for Time-Poor Workers
Flexible remote work handed you back 3 precious hours from your old soul-crushing commute. But your days still feel like they're running on ...
Read more
7 Flexible Remote Work Hacks for Time-Poor Workers
The Future of Work
How Remote Work Unlocks AI Superusers with Darren Murph
Darren Murph helped define the first era of distributed work. As GitLab’s Head of Remote (and the first person ever given that title), autho...
Read more
How Remote Work Unlocks AI Superusers with Darren Murph
The Future of Work
How to Build Real Expertise When AI Does the Grunt Work
Your Zone of Genius has a training problem. So does mine. It’s true, AI can make you look more capable before it makes you more capable. It’...
Read more
How to Build Real Expertise When AI Does the Grunt Work
The Future of Work
How to Stop Social Offloading from Hijacking Your Remote Team
Ever used AI to respond to a team email, DM or give feedback on a key project? Everyone’s doing it these days. Companies have been falling o...
Read more
How to Stop Social Offloading from Hijacking Your Remote Team
previous
next
Crossover Logo White
Follow us on
Have a question?

Get answers to common questions using our smart chatbot Crosby.

HELP AND FAQs
  • About Crossover
  • Companies Hiring
  • Resources
  • What is WorkSmart?
  • High-Paying Remote Jobs
  • Selection Process

Join the world's largest community of  AI first Remote WorkersAI-first remote workers.

Find your dream job
Hire Top Talent
© Crossover, 2026
Website TermsContractor TermsPrivacy PolicyLegalCookie Settings