Iwo Szapar

Hybrid Work Expert

AI Maturity Index

In a world where 77% of leaders won't consider candidates without AI skills, understanding your AI maturity isn't just nice to have — it's career-critical.

Introducing an AI adoption GPS - showing where you are, where others are heading, and your fastest path forward.

That’s exactly what we’ve built: a 15-min diagnostic tool powered by real-world data from thousands of professionals.

It's simple 
1. Chat with our AI assistant for 15 minutes about yourself and your AI usage 
2. Get an instant 5-page report with scores, benchmarks, and personalized coaching 
3. Run group reports for your whole team or company

Co-Creator

Ministry of Communications and Information Technology of Saudi Arabia

Co-hosting a program for 22 Saudi AI startups in building production-ready AI agents from concept to deployment. 

Key Focus Areas:
- AI agent architecture and orchestration strategies
- Business model innovation for AI-native companies
- Go-to-market positioning in the MENA region
- Technical troubleshooting and implementation guidance
- Strategic planning for scalable AI solutions

Working alongside the Kingdom's Centre of Digital Entrepreneurship and Saudi AI Leadership Forum to accelerate the next generation of AI companies leveraging Saudi Arabia's unique regulatory clarity and infrastructure advantages.

Program Highlights:
- Weekly workshops on agent development and business strategy
- 1:1 coaching sessions with individual startup founders
- Office hours for real-time technical support and troubleshooting
- Demo day presentations to industry leaders and potential investors

Supporting entrepreneurs who understand that sustainable AI competitive advantages come from workflow integration, cultural intelligence, and solving real customer problems - not just having the latest models.

AI Advisor

Supporting the „Tech Founders” program

Startup Mentor

South Summit

Working with South Summit's global team to connect startup founders with investors and corporate partners across Asia, Europe, and Latin America. Part of a hands-on community that's built 100+ successful exits and facilitated over $17B in startup funding.

AI Ambassador

Saudi AI Leadership Forum

Together with 350+ AI Enthusiasts 🇸🇦, we are dedicated to exploring the vast potential of AI as Saudi Arabia embraces Vision 2030, fostering a community where ideas flourish and connections are made. 

Our mission is to empower each member through insightful discussions, expert-led workshops, and collaborative projects. Whether you're a seasoned AI developer, a business leader seeking to harness AI's power, or simply AI-curious, we offer a platform to learn, share, and grow.

Chief AI Officer & Founder

Remote-First.Institute

Fixing change management with AI. 

- User Expansion: From 319 users in Q3 2023 to 2,003 users (8% paying) in Q2 2024
- Revenue Growth: From $148 in Q3 2023 to $10,635 in Q2 2024
- AI-Assistant Deployment: From 1 AI-Assistant in Q3 2023 to 201 in Q2 2024

🚀 The Journey Begins

In spring 2023 we were looking for ways to productize the "Remote Work Audit" that we've been successfully selling for many years at Remote-how. We decided to experiment with how AI can help. 

During two hackathons with Google and OpenAI, we created a simple prototype and brought it to users. They loved it, so we continued building which led to the creation of AI-Mentor, and eventually getting into an AI Accelerator Program in Saudi Arabia. 

Today AI-Mentor is a change management platform designed for consultants. It offers AI-enhanced interview toolkits, multi-stage AI-Assistants, and workplace analytics. These tools streamline consultancy operations and improve client engagement.

🧠 Projects I lead within AI-Mentor:

1. AI-Powered Remote Work Audit  

- Insight: Productized the "Remote Work Audit" using AI-Assistants.
- Impact: Evaluates remote work capabilities across 120 essential areas during an async conversation with employees, providing deep insights and actionable recommendations to enhance productivity.

2. 30-Day AI Productivity Experiment

- Objective: Conducted a 30-day experiment where 300 ambassadors were given access to an AI Productivity Partner.
- Result: The AI Productivity Partner helped participants stay as productive as possible by managing their calendars, planning tasks, scheduling deep work sessions, providing daily coaching, and offering productivity scores.

3. AI Hackathons

- Initiative: Hosted multiple hackathons (virtual & in-person), engaging over 400 participants.
- Outcome: Empowered participants to build custom, no-code AI tools, significantly enhancing productivity and addressing workflow challenges.

Maker @ AI-Mentor

We are a not-for-profit organization on a mission to create a space with open-source and expertise knowledge about the remote-first work approach provided by the world’s leading future of work experts.

We launched the Remote-First Institute to:
- Counteract the global "back to the office" movement.
- Create Global Standards for companies on remote-first processes.
- Produce high-quality events, articles, reports, and analyses.
- Cultivate a global community for remote-first experts.

Head of AI Projects & Co-founder

▪️Advised 3,000+ companies, incl. Walmart, Microsoft, ING Bank, and Deloitte on how to work smarter.
▪️Spoke at 200+ events, incl. Global AI Summit, South Summit, The Next Web, Running Remote.
▪️Featured by BBC, Forbes, Prezi, Remote, HR Exchange Network, and more.
▪️Built a global community of 31,000+ people who believe work can be done from anywhere.
▪️Wrote a book "Remote Work Is The Way", alongside experts from Netflix, GitLab, and Mural.

Strategic Advisor | Community Builder | Speaker | Writer

Remote-how

Remote-how is the leading platform for remote work education and consulting, helping over 3,000 companies optimize their remote work strategies. We have built a robust community of 25,000+ remote work professionals and collaborated with 250+ experts from renowned companies such as Netflix, GitLab, Microsoft, Mural, and Hubspot. 

Our partners include industry leaders like Asana, Remote, Deel, Prezi, and Safetywing.

💡 Key Projects:

1. Remote-how Marketplace

- Overview: A consulting and virtual training marketplace connecting companies with top remote and hybrid work experts. The marketplace facilitates the hiring of experts for audits, consulting, workshops, and content creation.
- Impact: Provided companies with access to specialized remote work expertise, improving their operational efficiency and remote work practices.

2. Remote-how Academy:

- Overview: The first global, online education and certification program covering essential remote work skills and tools. The academy offers tailored programs for remote workers, HR professionals, and managers.
- Programs:
* Certified Remote Manager
* Certified in Remote Human Resources
* Certified Remote Individual
- Impact: Educated and certified hundreds of professionals, enhancing their ability to effectively manage and thrive in remote work environments.

3. Remote Future Summit:

- Overview: Until 2020, it was the world's largest virtual conference focused on remote work, gathering industry leaders, experts, and practitioners to share insights, strategies, and innovations in the remote work field.
- Impact: Hosted thousands of participants globally, providing invaluable networking opportunities and access to cutting-edge knowledge on remote work trends and best practices.

CEO & Co-founder

Microsoft

I hosted a series of open webinars and invite-only workshops about hybrid work best practices for the Microsoft community and clients.

Remote Work Advisor

I helped build the first in the company's history "Hybrid Work Playbook".

Walmart

I worked with the HR team on Walmart's CEO's remote work strategy proposal.

🚀 Remote-First Activist | Top 50 Remote Influencer | Since 2017, shaping the future of remote-first world

Aloha, I'm Iwo Szapar! I help build future-proof organizations at the intersection of AI and human potential.

🌍 Key Achievements:
- Transformed work approaches at 3,000+ companies including Microsoft, Walmart, and ING Bank
- Co-created the AI Maturity Index with Harvard researchers, democratizing enterprise-grade AI readiness insights
- Established the Saudi AI Leadership Forum and co-founded AI-Mentor to accelerate organizational AI adoption
- Built a global community of 25,000+ professionals championing location-independent work
- Created an expert network of 250+ consultants from companies like GitLab, Netflix, and Hubspot

My work gathered recognition from Forbes and BBC. I authored "Remote Work Is The Way" and have spoken at over 150 events incl. Web Summit, South Summit and The Next Web, while living in 15 different countries.

Born in Gdansk, Poland, I've embraced the 'slowmad' lifestyle that informs my perspective on the future of work. When not researching AI applications, I'm reading history books, surfing, or DJing with my dog Luna nearby.

Connect to explore how AI can help your company work smarter! 🚀

🚀Remote Work Advocate & Co-founder

Remote-how helps companies make remote & hybrid work, work. Since 2017. 

🤓 Remote-how Marketplace - the world’s leading remote & hybrid work experts marketplace. Work on your consulting and advisory projects with 200+ pre-vetted practitioners from top distributed companies. 

🚀 Remote-how Campus - a community where leaders of hybrid teams come to connect, learn and grow together with access to live leadership development programs, mentoring services, and more.

Going viral was fun until I tried replying to thousands of “CLAUDE” comments manually.

Simular built a tool that helps turn that kind of chaos into organized leads instead of 4 a.m. wake-ups.

Two weeks ago I posted about building my second brain with Claude Code.

Offered a PDF to anyone who commented “CLAUDE.”

It exploded.

Day 1: I was Superman
• Every “CLAUDE” comment → I checked if we’re connected and sent a DM or connection request.
• Every custom question → I drafted a thoughtful response.
• Every Chief AI Officer or Big4 partner → Mental note to follow up.

I felt on top of everything.

Days 2-5: I was drowning
• 300+ comments per day
• 30k LinkedIn connections limit hit
• 90% of my responses were copy-paste
• 10% were brilliant questions I actually wanted to answer

My sleep schedule: 4am wake-ups to “catch up”. 

Days 6-14: I accepted defeat
• Replied to maybe 30% of the “CLAUDE” comments
• The Big4 partner who wrote a paragraph about their use case? Still unread
• The CAIO who said “genius, let’s chat”? 

Lost in the noise.

⸻

What I should have done on Day 1

Opened Simular 1.0 on my desktop.

Think of this a an “Autonomous Computer”.

Like n8n, but for everything - apps, web, files. And it stays local, not cloud.

Chatted with my new friend Bigfoot:
🦶 “Looks like you’re going viral. Want to automate comment responses?”

Then trained the system like an intern:
• “See this comment that just says ‘CLAUDE’? Reply with the PDF link.”
• “This one asking about Notion vs GitHub? Draft a response, I’ll review it.”
• “This person mentions ‘consulting firm’ + ‘interested in team setup’? Add to HubSpot, tag: Enterprise prospect.”

Hit Save. Workflow locked in.

Then it runs in the background - while I record podcasts, take calls, actually sleep.

⸻

The result I wanted
• 4,700 “CLAUDE” comments → Auto-responded ✅
• 400 custom questions → Pre-drafted for my review ✅
• 150 qualified leads → Added to CRM with context ✅
• Bigfoot flags 12 comments it’s not sure about (including that Big4 partner) → Gets my personal attention ✅
• Me → Actually sleeping ✅

What actually happened
• I manually typed variations of “Here’s the link!” 1,500+ times
• Lost 3,000+ people to notification fatigue
• Probably missed 50+ real business conversations

⸻

This is what Simular 1.0’s human-in-the-loop is built for

You train it once:
• “CLAUDE” comment → send PDF
• Complex question → draft response
• High-value signal → CRM entry

It learns. Saves the workflow.
Runs it while you’re doing literally anything else.

You wake up to organized, pre-handled responses.
You review in 20 minutes, not 8 hours.

Next time I go viral, I’m ready on Day 1.

Try Simular 1.0 - link in comments. 🚀🚀🚀

What would you like to automate on your computer? Share in comments and let’s explore together if it’s (already) possible!

Brand partnership • Co-Creator @ AI Maturity Index 🚀 | Entrepreneur, Writer, Speaker 👨‍💻 | 15 countries called home 🌍

Co-Creator @ AI Maturity Index 🚀 | Entrepreneur, Writer, Speaker 👨‍💻 | 15 countries called home 🌍

Helping GTM Leaders & Founders Grow With GTM x AI | Fractional CxO | Building Linkedin Tools @ humanoidz.ai

this is the closest i've ever felt to 'work' AGI...
I'd even say this is potentially the best investment of your time
when asked what's the 20/80 signal vs noise to focus on atm, I answer this:

claude code + sub-agents + skills... hear me out:

most people use claude like a chatbot. ask a question, get an answer, repeat.
i've been using it like a powerful team, that gets me...

here's what changed: claude now has skills and sub-agents. skills are basically recipe cards you create once, then claude follows them perfectly every time. no more rewriting the same prompts. no more inconsistent outputs.

sub-agents take it further. instead of one claude doing everything, you create specialists. one for linkedin content. one for data analysis. one for email drafting. each one remembers your preferences forever.

(someone in our community said "this replaced everything. i barely use any other tools anymore.")

the real magic? you can run 3-4 agents simultaneously. while one analyzes a spreadsheet, another writes a post about those numbers.

anyway, i put together a full playbook covering: 
→ setting up skills and enabling code execution in claude 
→ creating your first SKILL.md file (claude literally writes it for you) 
→ the debug loop that makes skills sharper over time 
→ building sub-agents with their own "brain" folders 
→ connecting agents to google drive, slack, hubspot via MCPs 
→ the packaging mistake that breaks everything

it's 20 pages of step-by-step stuff that took months to figure out.

want it? you know the drill: 
1. 👍 like 
2. 💬 comment "augmented" 
3. 🔄 repost just to be sure
will send it later today.. first come first serve as there are limits.

(make 100% sure we're connected)

DM me if you have questions.

Claude_Code_Claude_sub-agents_and_Claude_skills

using AI for 1000+ days...canceled most of my AI subscriptions this month.
now i spend 90% of my time in one tool.
this is probably the best time investment you make this year...

yesterday's post about claude code/agents/skills did better than expected so i'm releasing the FULLER playbook. the tool? claude code. but i don’t code a single line. don't let the "code" in the name fool you… i'm not a developer and it works perfectly. 

here's what happened:
chatgpt, gemini, the tools I used etc forget everything. every chat starts from zero. you re-explain your project, your brand voice, your preferences... over and over. even with customgpts and claude projects it isn't reliable enough..

claude code changed EVERYTHING. you create a simple file called CLAUDE[.]md. that file becomes your AI's permanent memory. write your context once. never repeat yourself again.

but here's where it gets REALLY interesting:
you can build sub-agents. specialists that each have their own "brain folder." one for linkedin content. one for research. one for client work. each remembers everything.

then you connect them to your actual tools via MCP: hubspot, gmail, google analytics, notion, slack. they execute tasks on your behalf. i'd say this is probably the biggest practical shift in knowledge work since the chatgpt moment. and it's simple. it's basically just folders and markdown files. no actual coding required. true story...someone in our community said it best: "my clients think i hired a team."

anyway, i’m sharing and i've used the playbook from Iwo Szapar which covers it in perfect easy-to-follow details, step by step:

→ setting up claude code (even for non-coders) 
→ creating your CLAUDE.md file (your project's permanent memory) 
→ building sub-agents with their own brain folders 
→ connecting to hubspot, gmail, notion via MCP 
→ the mistakes that break the whole system 
→ ready-to-use templates you can copy

this might be the best hours you invest this year.

want it? you know the drill
will send it today if you’re fast (there are some limits on number of DMs per day…first come first serve:
1. 👍 like
2. 💬 comment "Second Brain"
3. 🔄 repost just to be sure

(make 100% sure we're connected)

thank me later for this one...

how I built a second brain that actually works

Remote Skills Academy by Livit

An impact-focused education platform for Indonesians (and now expanding worldwide) who want to learn to work online, build successful remote careers and live life on their own terms.
Upskilled and reskilled 10,000+ alumni over the last 4 years.

Founder

Livit

CEO Livit International & Founder Livit Hub Bali

General Manager Project Getaway, Livit Spaces

Remote-first.Institute

A not-for-profit organization on a mission to create a space with expertise and knowledge about the remote-first work approach provided by the world’s leading future of work experts.

Founding Member

Bali Investment Club - BIC

Angel Investor

Plumia

Plumia champions global mobility rights for people everywhere and aims to build a country on the internet. Our work spans research, policy, technology, storytelling, and design, and we aim to bring about a human-centric future where a person’s birthplace does not restrict their access to work or life opportunities.

Member

Uncommon

Uncommon is a platform where the world's top female talent come to connect and level up. Our fast-growing community and action-oriented programmes are designed for the many facets of the modern successful woman.

Project Getaway

Curated, inspiring workations, retreats & getaway experiences in tropical Bali for entrepreneurs and startup teams.

Managing Partner

The P World

•	Launched and managed operations for the Azerbaijani market, including business development, legal & finance, logistics, recruitment & staff coordination, customer relations, marketing & PR, partnership initiation and delivery.
•	Worked with a portfolio of international event brands like the "Marketing Kingdom", "HR Experience", "PR Experience" which feature speakers representing some of the most recognized entities on the globe: the Royal British House, Facebook, Google, Rolls-Royce, the Olympics Games, Lego, etc.
•	Organized the first business excellence awards in Azerbaijan ("Excellence in HR", "Golden Crown Marketing Awards"); 
•	Collaborations involving the launch in Azerbaijan of "The Economist" publications; consultancy services for government agencies; public relations campaigns for projects like the first Hollywood star endorsement for a local brand.

Managing Director

Handled the local side of the PR campaign, business development and logistics for the first P World project in Azerbaijan.

PR & Business Development Manager

AIESEC Iasi

Coach

Managed a team of 6 people who was in charge of organizing a recruitment campaign, various conferences and events related to it, an induction program.

Project Manager

Outgoing Exchange Team Lead

AIESEC in Azerbaijan

•	Established media relationships in order to promote the AIESEC projects.
•	Developed strategies for strengthening the AIESEC presence in university campuses. 
•	Trained AIESEC members on communication, PR, marketing, project and event management, intercultural exchange, finance-related issues. 
•	Coached and mentored project managers, team leaders and exchange participants
•	Supervised and found ways to enhance the budgets raised for the country management office, local offices and their projects. 
•	Together with the other VPs, elaborated and implemented HR (especially recruitment and talent development) processes, tracking and performance appraisal systems.

National Vice President - Communication and Local Development

Founder of Livit Hub Bali & Remote Skills Academy | Future of Work Advocate | Speaker APAC & EU | WoP7. BASB14. Uncommon '21.

Over the last decade, at Livit, we've helped develop 100+ business ideas and dozens of remote-capable teams. 10+ million people across 60+ countries have been reached through projects started in our ecosystem. Headquartered at Livit Hub Bali, we have been ranked as one of Asia's Best Workplaces and received several other awards for our organizational culture.

The Remote Skills Academy, which I founded in 2020, is an impact-focused education platform that has equippd 10,000+ Indonesians and other youth around the world with digital and remote work skills. We are currently expanding via partnerships in Africa and Europe.

I am also a Founding Member of Remote-First Institute, an angel investor, and an advisor/board member to a handful of other exciting companies and projects.

I am passionate about the future of work. I believe that when we design more purposeful, sustainable businesses and lifestyles, we shape a better reality. I have spent the last 10+ years studying and understanding the mindset, practices, and tools required to make that happen, and I am excited to share my expertise.  I have received multiple distinctions for my work in culture shaping, leadership, and business development, including being a Top 50 Remote Innovator in 2023 and 2024, and my work was featured in publications like Washington Post, CNET & more.

My professional and personal experiences span 4 continents, 45+ countries, and several different industries. I am based in Bali for most of the year and a digital nomad/location-independent entrepreneur for the rest.

My fields of expertise are new ways of working, modern leadership, organizational design & culture, work-life synergy, sustainable entrepreneurship, human capital development.

Lavinia Iosub (Yo-soob)

After an (always delightful) exchange with Paul Millerd the other day, I thought of this piece I wrote a few years ago.
It aged well - maybe because it came from a (pre-AI writing) moment when I was inching towards burnout, took a sabbatical, gained perspective… and eloped to marry my partner of 10+ years 😄 💍 
Burnout keeps popping up in so many conversations I'm having lately. 
And I love David Heinemeier Hansson's point: many people only ever get a real reset by quitting - so that's what they're doing when they need one. Sabbaticals flip that script.
At Livit, we believe in that, and we offer them to anyone who’s been with us 5+ years. (I’m currently working with Agnes, one of our leadership team members, on planning hers, in fact).
There's a ton of talk (and books, and courses, and resources) about productivity. And don't get me wrong, I love me some productivity know-how, no one needs to unnecessarily stretch 1 day worth of work into a full week, because they can't prioritize, organize their time or stay focused.
But there isn't enough talk about rest and recovery, which are integral parts of "performance".
Not separate from it. 
Not to mention, they're also integral and highly important parts of... living and enjoying life.
Here it is 👇 , for anyone who might need this read this weekend.

Lavinia Yosub (Iosub)

Founder Livit Hub Bali & Remote Skills Academy | Top Future of Work Innovator ’23, ’24, Top Future of Work & Ed Voice ’25 | Venture Builder & Angel Investor | AI-fluent, people-first

Open article: On egg baskets & business interludes by laviniaiosub.substack.com

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The Battle

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Followers

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Engagements

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