Iwo Szapar

Hybrid Work Expert

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

Aloha, I'm Iwo Szapar! Over the years, I've helped transform how over 3,000 companies approach work, leading to more efficient and enjoyable professional lives. 🌍

Key Achievements:

▪️Co-created the AI Maturity Index with Harvard researchers, democratizing access to enterprise-grade AI readiness insights
▪️Advised Ministry of Communications and Technology of Saudi Arabia on AI up-skilling for startups
▪️Launched world's first certification program for remote workers: Remote-how Academy, back in 2018.
▪️Established strategic partnerships with 150 companies, including Asana, Deel, Remote, and Safetywing.
▪️Created an expert community of 250+ consultants from companies such as GitLab, Netflix, and Hubspot.
▪️Co-organized 3 editions of Remote Future Summit, reaching over 11,000 attendees and featuring 140 speakers.

Born in Gdansk, Poland, I've embraced the 'slowmad' lifestyle, living in various countries while working remotely. This journey has enriched my perspective and fueled my passion for innovation. When I'm not working, you can find me reading history books, following international affairs, or indulging in my hobbies as a dog lover, amateur surfer, and DJ.

Connect with me to explore how you/your company can 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.

🚀 Our AI Maturity Index got acquired by ISG (Information Services Group).

Didn’t think a random virtual coffee with a stranger would turn out this way...

18 months ago, Eryn and I started talking about AI adoption chaos.

Everyone had opinions.
Nobody had data.

We launched this as a research project.

It evolved into a diagnostic tool.
Using AI to assess… AI maturity in under 15 minutes.

Our system interviewed 6,000+ professionals across 75 countries.

The data was clear:
• 92% of companies are increasing AI investment
• Only 1% consider themselves AI-mature

Companies weren’t struggling with AI tools.

They were struggling with knowing where to start.

ISG noticed.
They partnered with us.
Then became our biggest client.

Today, they acquired us.

That’s not how acquisitions usually work.
But maybe it’s how they should.
They knew the product deeply.
We knew their vision.
The fit was obvious.

ISG brings research capabilities we couldn’t build alone.
Global reach to take this from thousands to millions.
Resources to turn our platform into enterprise infrastructure.

I’m genuinely excited about what we’ll build together.

Now, zooming out for a second.

It’s been 8 years of building.

First Remote-how.
Then Remote-First Institute.
Now AI Maturity Index.

Many mistakes.
Many lessons.

And now — first exit.

I’m relieved before I’m excited 😅

Eryn — you made this possible.

That “virtual coffee stranger” became an incredible co-founder who pushed me, challenged me, and helped me grow fast.

Thank you. Truly. ❤️ 

Fun fact: we met only twice in real life. 
Once in Lisbon (where we decided to launch the company together - see picture), and second time in Saudi Arabia.

This entire journey was 100% remote.

To the 6,000+ people who took the assessment and trusted us with their data:
You made this possible. Every benchmark came from you.

To Steven, Hannah, and the entire ISG team: You believed in the platform long before the acquisition. That partnership gave us confidence this would work. Thanks a bunch!!!

And to everyone who thought:
“Just another AI survey” — fair skepticism.
We had to earn trust with data quality.

Now we close the 92% / 1% gap.

At scale.

With resources that matter.
Companies investing in AI need to know where they stand.
We’re building the infrastructure to show them.

PS. Yes — I am VERY excited. Like… a lot.

PS2. Full press release → link in comments 👇

Co-Creator of AI Maturity Index (Acquired by ISG) 🤙 Vibe Worker

Building Marketing Waiting Rooms™ - Join the community 🦄 | Content | Demand-Gen | Inbound

I practice the art of staying top of mind 🧠 This means I help brands clarify their message and bring it to life in unforgettable social content and ads.

Justyna Ciecierska-Göçeryan

When I was a marketing intern I’d drink beers with our sales director and write ad copy on the back of a napkin.


Those napkin scribbles outperformed 80% of the campaigns I agonised over with the marketing team.

I honestly got along better with sales than my marketing colleagues.

Their world just made more sense to me LOL.
The sales floor was my church.

I'd lurk in the hallways, eavesdropping on reps pacing back and forth with their headsets on, totally in their flow.

I got to hear bizarre customer objections they handled.
I got to observe them close a deal everyone else had pronounced dead.
I got to know our customers so much better thanks to them.

And I think it’s beautiful 🫠

No grand revelation today. 

Just this:
Go grab a drink with your sales team.

They'll make you a better marketer.

What's the best thing you've learnt from your sales colleagues?

Justyna Ciecierska, MSc

Founder @ Marketing Waiting Room - Messaging & creative strategy

I stopped dumping detailed buyer personas docs into ChatGPT. I replaced it with 3 sentences. Content gets DRAMATICALLY better.


When you vomit a 20-page document into AI, it doesn't magically cherry-pick the most important things.

It sees 47 different directions it could take, and it tries to lump it all together into one generic, illogical content sludge.

If you want AI to generate HYPER-RELEVANT content that attracts your IDEAL buyers, you need to strip your targeting down to its essence.

You only need three elements.
Three short sentences.
That's it.

1. DREAM OUTCOME: What are they trying to achieve?

2. PROBLEM: What's getting in their way while chasing that dream?

3. PSYCHOGRAPHICS AND BEHAVIOUR: How are they wired? What makes their situation unique?

So for example:

Imagine you are a business coach helping people get their first customers.

Here's your audience:

DREAM: "They want to start their own business or are in the early stages."

PROBLEM: "Terrified of losing stability and wasting lifetime savings."

PSYCHOGRAPHICS AND BEHAVIOUR: "Perfectionists. Not business-savvy. Overwhelmed. Overthinkers. They think they have to have a perfect product before selling."

Now here’s the thing:

Two people can have the same dream, and even the same problem.
But if one is business-savvy and the other is an overthinker paralysed by perfectionism, they will be interested in different content.

See the difference:

Overwhelmed perfectionist: "How do you know your offer is good enough before you start selling?"

Business-savvy doer: "Here’s the fastest way to sell your offer so you can find out if it's good enough."

See the nuance?

AI needs explicit, non-ambiguous guardrails to know exactly who it's writing for.

And yeah, I know, stripping everything down to its core is annoying, uncomfortable work.

But trust me - once you do it AI content gets waaaaay better and you stop prompt-wrestling.

This is literally what I do when I set up an AI Content Brain for my clients:
I turn their messy targeting and messaging into something AI can easily use.

Want me to do the same for you?

Go to: marketingwaitingroom.com and book your intro!

Founder @ Marketing Waiting Room - Messaging consultancy

How this truck salesman uses a BIZZARE playbook to hijack your brain in 120 seconds.


You might think this sh*t is chaotic, super random and silly.
But it’s actually well thought-out.
Masterclass in attention and memory encoding.
Let me explain

1/ CURIOSITY GAP
The video starts with a man telling a woman:
“Lean back. Don’t worry. I’ll catch you.”
You immediately want to see how this ends so you keep watching.

Attention? Check.

______

2/ SHOCK AND PATTERN INTERRUPT

→ He lets her fall.
You feel shock. Confusion. Surprise. This breaks your expectation. Your brain is now more receptive to the message that follows. 

→ That's when he delivers a life lesson: “Don't trust anybody.”
Your brain assigns him authority and credibility. Then he adds: "Except when buying trucks - trust me". That’s his bridge to the product.

(btw notice how he uses that gigantic comb for no good reason to keep your attention).

______

3/ SHOWMANSHIP + NOVELTY BIAS

The guy doesn’t list features.
He PERFORMS the features.

→ He measures the truck’s length by doing mid-air splits
→ He pretends to be a doctor while “diagnosing” engine power

You might think it’s silly but it’s actually genius for two reasons:
1) The weirdness keeps attention high
2) The showmanship bypasses sales resistance

When people realise they’re being sold to, they instinctively put up mental defences and stop processing the message.

By wrapping the pitch in weird, entertaining behaviour, he prevents your brain from labelling it as “advertising,” so those defences never activate

______

4. MEMORY HOOKS

While you’re entertained, he casually encodes the USPs in your brain:
→ Engine power
→ Cargo box size
→ Comfortable interior

He uses memory hooks to ensure you remember the most important things:
→ The brand name
→ The product and its USPs

Dude keeps saying:
“Jerry… Jerry… Jerry…”
Jerry is the company name.
He repeats it so often that it burns into memory.

And the weird acts (doctor, splits, comb) act as memory glue.
Your brain links:
Jerry → weird doctor → powerful engine
Jerry → splits → long cargo box
Jerry → comfort → funny guy

After watching the video, your memory is left with the most important keywords:

Jerry
Chinese
Great trucks

NOW CHECK THIS:
Next time you need a truck, your brain will remember these keywords, and you will Google the,m and you will find them.

The reason AI content sounds generic has nothing to do with AI.

It's you.

You're dumping 20 pages of audience research and 47 pages of transcripts into ChatGPT hoping it will do the hard work of figuring out whom you're actually talking to.

It won't. That's your job.

AI doesn't need all that information.

It needs clarity.

Three sentences.

If you can't explain your audience in three sentences, your problem is not generic content.

Your problem is targeting.

Clarity in, clarity out.

Want me to ruthlessly clarify your targeting and messaging and set up an AI content assistant that writes hyper-relevant content?

Go to marketingwaitingroom.com and book your intro.

The term “long-term marketing” is misleading. It suggests that results take years to appear, but that’s not true.


We praise direct response marketing for its quick and measurable results:

> Show an ad
> Customer clicks
> Customer takes action

But there’s another part of marketing that feels more ambiguous.

It’s often labelled as “long-term,” “brand awareness,” or “brand marketing.”

But not many people understand its mechanics.

A good way to think about it is indirect-response marketing.

(Or how I like to call it - Marketing Waiting Room™) 

It works differently.

The purpose is to build something deeper: memory structures in the buyer’s mind that can be retrieved when a buying trigger hits.

These memory structures are what drive people to come directly to you or make your direct-response marketing efforts perform better.

This type of marketing is often lumped into the “long-term” category, making it seem vague and uncertain in its ROI.

The real issue is that many marketers don’t fully grasp how to make it work.

It requires a different set of skills, thinking, and approach.

It’s about creating a resilient and valuable asset.

One that lasts beyond any specific channel or campaign and doesn’t show up neatly on a dashboard.

But that doesn’t mean it takes years to see results.

If someone is exposed to marketing your assets that build memory structures and then experiences a buying trigger just days later, that memory will activate, driving action.

Over time, this memory structure gets stronger, and these effects become even more visible.

I’ve built an AI content system that doesn’t just generate content, it follows your strategy. And OMG, it works ridiculously well!

If you’ve followed my work, you know I’m annoyingly picky about content.

I care about relevance, nuance, originality, and quality.

So I’m not interested in cranking out more AI slop.

For me, it’s all about using messaging, targeting, content strategy and internal expertise to create on-brand, original content across channels.

I pre-package and pre-chew it for AI.
I call it the “AI Content Brain” and it works like a charm!

Why?

Because I strip down the strategy to its essentials and structure it in a way that AI knows how to use it when creating content.

To be clear, it’s not something I whipped up quickly overnight.

I've been obsessing over this since 2022.

Testing, breaking, refining.
Figuring out exactly how to make AI finally *get it*.

I’ve been offering this as a productised service for a few months now, and I'm opening new slots today!

In 3 weeks, you get:

→ Your positioning, messaging, targeting, and content strategy defined and compressed into a clear doc AI can follow, no 20-page-long pdfs

→ Your internal expertise, product info, opinions, stories, and IP extracted and structured so it can be easily reused across content

→ A Content Brain that gives AI the exact context it needs to stay on strategy and stop hallucinating

→ AI content assistants that turn any raw input, ideas, notes, transcripts, conversations into on-brand, high-quality content across channels

All set up for you in a tool of your choice: Gemini, ChatGPT, Claude - you name it.

So if you want to scale your content creation without losing your soul and substance, I would LOVE to build this for you!

Head to marketingwaitingroom. com and book your intro.

The future of AI content creation is: 'interview me until something worth posting comes out.’

Let me explain:

I worked with 7 clients last year.

I helped them define their positioning, messaging and content strategy and built an AI content system that creates on-brand content across channels.

But there was something I didn't expect…

These people are incredibly smart.
Brilliant at what they do.

They'd tell me stories that made me go "Wait THAT'S a post."

And yet they kept struggling with content creation.

How’s that possible?!

They had the expertise. They had the stories.
So what was missing?

It became clear when they tried the "Interviewer" feature I built into their content system.

An AI assistant that:
- Understands their audience and strategy
- Asks targeted questions
- Pulls out stories, opinions, anecdotes
- Surfaces angles they didn't know they had

THEY LOVED THAT FEATURE THE MOST!

That’s when I realised they didn't have a content creation problem.
They had an insight extraction problem.

All they needed was buried deep in their minds.
And they couldn't access it on demand.

The Interviewer changed that.

They kept telling me that this made them think in a completely different way.

It sparked ideas they wouldn't have had otherwise.

Opened doors they didn't know were there.

THAT’S WHAT MAKES CONTENT INTERESTING!

That's when I understood what content operations should actually look like:

→ LAYER 1: Extract insights from experts through a natural conversation with an interviewer AI assistant 

→ LAYER 2: Process it through an “AI Content Brain” trained on positioning, messaging, and audience 

→ LAYER 3: Remix into different formats and channels.

The expert's job is to think and talk. 
AI’s job is to turn that into original, on-brand content assets.

So if you want your expert team to create content stop asking them to write LinkedIn posts.

Start building systems that pull the best of what they know and then let the “AI Content Brain” do the rest.

Would you like me to create such a system for you?
Book an intro via the link in my bio!

B2B marketing has a technical addiction


Growth hackers
GTM engineers
Frameworks
Automations
Ratios


We treat marketing like an engineering challenge.
And we don’t want to admit that it’s mostly a communication challenge.

I came across this quote lately:

“The truth isn’t the truth until people believe you, 
and they can’t believe you if they don’t know what you’re saying, 
and they can’t know what you’re saying if they don’t listen to you, 
and they won’t listen to you if you’re not interesting, 
and you won’t be interesting unless you say things imaginatively, originally, freshly.”

Bill Bernbach figured this out decades ago, but somehow we convinced ourselves that B2B marketing works differently.

We’re excused from clarifying our message and allergic to a little art.

Is it because we think our products speak for themselves?
Or is it because we don’t feel like doing the difficult work?
Or is it because martech has led us to believe that we don’t need clarity and creativity if we have a good tech stack?

I don’t know.

But I do know this: clarity and creativity in marketing aren’t optional.

They’re THE job.

POV: LinkedIn Ads perform at Got Talent...

I wish more B2B marketers and founders knew that…


1. Brand is your silent salesperson

2. Having no competitors is usually a bad sign

3. Signing up to a newsletter doesn’t mean someone is in "consideration stage"

4. Building brand awareness means building mental availability (buyer memory)

5. A marketer’s job is to make the brand easy to recall and easy to buy

6. You shouldn’t “scale marketing” before you’ve decided on positioning and messaging

7. Good advertising kills bad products

8. Creativity in marketing isn’t optional. It’s THE JOB

Couldn’t come up with 10. Help? 😅

My content workflow lately: I talk out loud to my “AI Content Brain” for 15 minutes on Monday mornings. Then it remixes my answers into endless posts.


That’s it.

Since I built my AI Content Brain in Claude, my content workflow got 

SO.
MUCH. 
EASIER.

And weirdly, way more fun.

Here's what I do now:

STEP 1: I start with the "interviewer mode"

Claude asks me questions as if it were my ideal buyer.
I just answer out loud (I use WisprFlow)
Casually. No writing. No pressure.
You would not believe what comes out of your brain when you're not trying to "write."


STEP 2: Claude remixes my answers into endless content pieces

It doesn't just summarise. 
No, no.
It does something more sophisticated.

It filters my rambling through my specific Targeting, Messaging & Positioning rules.

This means it knows what I sell, my unique PoV and what my target audience is interested in.

The Result:
→ 15 minutes of talking = 5-10 high-quality LinkedIn posts.
→ It’s not "AI-generated." It’s "AI-extracted."
→ The thoughts are 100% mine. The typing is 0%.

So here’s my advice to you:

Stop trying to create content from scratch.
Start having conversations and let AI do the remixing.

Want me to build your AI Content Brain for you?

Go to: marketingwaitingroom (dot) com and book your intro.

How to deal with messaging and content in an emerging vs. a mature market
TLDR: 

- Emerging market: your goal is to make your brand name = category. Which means your messaging and content should be category-focused. Not differentiation-focused

- Mature market: your goal is to communicate why your solution is better than the default. Which means your messaging and content should be differentiation-focused. Not category-focused.


EMERGING MARKETS:

Context:

→ Few competitors and no clear category leader yet
→ The real race isn’t differentiation. It’s becoming the obvious choice for the category
→ Low and uneven buyer awareness: many don’t know the category exists or don’t understand it
→ Buyers feel the problem but lack the language to describe it 


Messaging & content goals:

→ Create category awareness
→ Associate your brand with the category
→ Establish shared language: Frame and name the problem and the solution
→ Proprietary naming helps create associations (e.g. GTM engineering, Clay tables)

MATURE MARKETS

Context:

→ Many competitors and a clearly defined category
→ Buyers understand the problem and the available solutions
→ One or more strong leaders already exist
→ The game is differentiation

Messaging & content goals:

→ Clearly articulate how you are meaningfully different from the default options
→ Justify switching
→ Question what the category has normalised, or what is outdated etc. (e.g. Basecamp's calm work philosophy)

If I were Head of Marketing with a $300K+ budget, the first thing I'd do is:


Decide what our brand should be known for.

Don't forget this:

You're not investing $300K+ in channels.
You're investing in spreading a message.

TAKE THAT SERIOUSLY.

It's what makes your big girl budget deliver big girl results.

Pretty please, don't reduce yourself to 

a traffic factory 
a leads generator 
an ROI calculator

You're the architect of the big idea.

The thing people remember. 
Repeat. 
Talk about at dinner. 
Mention to their boss in every Monday check-in.

You're here to create something people are impressed by. 
Inspired by. 
Attracted to.

That's your real job.
The clicks and leads will come... wait, scratch that... they'll POUR in as a result of that.

Brands people can't stop talking about stand for something and own it:

→ Basecamp: "It doesn't have to be crazy at work" 
→ Gong: "Sales call reality over opinions" 
→ Intercom: "Marketing is conversational" 
→ Miro: "Where teams think together" 
→ Lovable: "Build something lovable"

So tell me - what's the one thing you want living rent-free in your buyer's brain when they finally have the problem you solve?

Why your “TOFU” or “demand” or “brand” campaigns are not working.


Because you’re trying to run them before you’re clear on what they’re meant to do.

Not many people realise that these campaigns are supposed to achieve mental availability.

Which simply means that your brand is top of mind when buyers realise they have specific needs and wants.

Like: When I need to decorate my house and I want it to be stylish, but also functional I think IKEA.

Or: When I need to improve how my sales team performs and I want clear, objective insight into what actually closes deals, I think GONG

This should be your starting point.

If you don’t define the needs and wants that your brand satisfies in one sentence like above, you don’t have the foundation for demand gen.

You end up with Frankenstein ads communicating everything and nothing.

They are hard to understand.
And therefore are hard to remember.
And therefore they will not work.

This gets especially painful in B2B software companies that kept adding features, use cases, integrations, and personas…

…until nobody can explain in one sentence when someone should think of them.

When this happens, the smartest thing to do is to hire an expert to help you boil it down to one simple message.

Otherwise you’re setting your marketing budget on fire.

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Iwo Szapar

Justyna Ciecierska-Göçeryan

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The Battle

Iwo Szapar

Justyna Ciecierska-Göçeryan

Followers

Posts

Engagements

Likes

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