I applied to 1001 jobs and wrote a viral article about it. This is what happens next. Part 2.

Preface

In Spring 2023, I resigned from the CEO position of a $100M creator economy FinTech and began to search for my Next Big Thing. I treated it as an experiment: what would happen if skilled C-level applied to 1001 jobs and documented every step of the way?

In June 2023, 🔗 I wrote an article that summarised my research.

I couldn’t imagine that my story went viral — with around 100k reads on Medium and countless reposts on LinkedIn and other platforms.

This is the story of what happened next.

Acknowledgements

I want to start a second article with deep gratitude to everyone who reached out to me to express support, offer collaboration or share their own stories.

The main thing I gained from my sudden publicity — are you, dear readers.

Thousands of outstanding professionals from over 50 countries flooded my LinkedIn to say — “Me too! I had a similar experience!”

Different ages, countries, ethnicities, and industries — almost all of us faced similar struggles at some stage of our careers.

I learned hundreds of unique stories, much more brutal than mine. And it’s fair to say that this was not my story. It’s our story.

I just had the privilege to craft it out.

How I Spent the Summer

Since the story went viral, I received loads of messages and had dozens of meetings with great people to discuss opportunities for potential collaboration.

I quickly gave up answering anonymous comments on Medium and other places and focused on people who put time and effort into writing personal messages on LinkedIn.

At first, I agreed to every meeting, but soon enough, their number became overwhelming, and I had to filter it.

People expressed interest in my experience, and their projects often impressed me.

However, the match wasn’t happening.

Some conversations were to discover common interests. Some were real jobs or partnership discussions. But many, which was an unpleasant surprise, were just offers of one-side risk-free terms (“work for free”).

I want to apologise to everyone whose message remains unanswered, whose meeting I declined or whose connection was lost.

In most cases, I was too drained, overwhelmed and discouraged to handle another conversation. Nothing to be ashamed of — rejections are painful, especially in such volume.

That’s weird, isn’t it? No match for 60 meetings?

– Maybe you can’t made up your mind what you were looking for? Are you still thinking you can get a CEO job out of the spot?

Of course not.

Even before the article, I already determined my dream job and a vision where I could bring the most value.

• VC roles
• Venture builder
• Entrepreneur-in-residence
• Incubator/accelerator leader
• Multi-startup studio leader
• Internal startup studio leader within a company
• Scaling complex tech product company
• Science-related projects
• Operations within medium-scale enterprise
• Complex marketing and growth within the funded venture

I was keen to join any existing ventures whose product or idea would resonate with my strengths.

Meanwhile, most of the offers were about helping startups get funding for the commission, being a fee-based salesman or marketer, or helping to penetrate the UK market without a budget.

So, I decided to focus on VCs.

The Shortest Career of Venture Capitalist Ever

I joined a VC networking group and quickly learned that getting into VC from the outside is impossible, no matter how skilled you are. They rarely hire, inner circle only, and you need to be in the industry for 5+ years or start from the internship.

So I did.

I humbled myself to a pro bono apprenticeship, found a small VC and offered my time for £1/month.

It solidified my experience in investment memos, valuations, industry research and financial modelling while I worked on it for two AI startups.

The team was impressed by my expertise, pace and industry knowledge but honestly said that having a partner-level intern with no salary creates pressure on them, and they can’t follow my rhythm (they worked on one or two deals every eight weeks, and my velocity was too ‘enthusiastic’ for them)

A month later, they invested in a startup for which I wrote an investment memo and led due diligence. So, at least my pro bono work served someone.

I also reached numerous large UK and global VCs. All said the same — no roles for me.

As a result of this attempt, even though I had a strong focus, a proactive approach and some network — by the end of the summer, I still had no offer.

From Survive to Thrive

Disclaimer: It’s not a survival story.

I don’t complain that I can’t find any job. I can’t find The Job.
My next Big Thing. The project I’ll dedicate to the next part of my life.

Most of us, young professionals, seasoned industry experts and tech entrepreneurs, don’t want any job.

Usually, we can support ourselves with side hustles, do consultancy or help our old clients or colleagues.

But what we want is The Project. Something we’ll commit ourselves to for years.

It’s about switching from survive to thrive.

The August’s Pivot

After all the meetings, learnings and insights, I decided to pivot my search and focus on my other strength. As everyone advised, I focused on a particular area of my expertise.

Hypothesis:

1. My CEO profile scares and distracts recruiters. Usually, 🔗 CEOs make around 300–600k in salary + shares and benefits level up earning to millions. (unfortunately, I had never made anything even close to these figures, but I appreciate that recruiters would assume it anyway)
2. The C-level positions in a CV also scare recruiters.
3. The career path should be consistent and demonstrate growth.
4. You have to show that you pose no threat to the current C-level.
5. CV should be tailored to every position (keywords, experience, accomplishments…).

I started with research.

First, I contacted people with whom I worked for the previous decade and asked them what they would name as my strengths:

Marketing, product innovation and repacking.

So, I decided to focus on the product.

1. I researched companies I have been previously rejected by and found profiles of their product leaders.
2. I tried to find people hired for the positions I’ve been rejected for, or at least to understand the profiles of people working at those companies. But many positions were unfilled, while others were occupied by promoting internal candidates. (!)
3. I also studied vacancies and asked GPT to find patterns, keywords, skills, and experience most needed for them.

Some of my findings:

💡Companies love it when a person grows at the same company and sticks to the same domain.

💡The career path should be consistent and demonstrate growth from individual contributor to expert and eventually to a leadership position.

💡Better keep the ceiling high enough to demonstrate that you have at least two+ stages to grow (VP, SVP, C-level)

💡Industry/niche experience is the key

That’s how I created my new product-focused profile and CV and began targeting FinTech.

From C-level to Product Manager

I rewrote my LinkedIn page completely and refined every position in my CV.

By repositioning myself to product leadership and innovation, I eliminated any C-level experience and downgraded myself to the Director level, Head of Product or even Product Manager.

I even went further.

💡I created an extensive mind map and adapted it to EVERY position I applied to demonstrate how the job description aligned with my experience and to showcase some docs, materials, and my mindset.

(spoiler: complete waste of time!)

💡Then, to make it even more visually attractive, I created a deck with my profile presentation, putting everything together and again aligning my expertise with the position requirement.

Spoiler: again, a time-wasting practice. No one ever looked at it.

And, of course, I tailored my CV to EVERY position I applied for, rewriting sections, adapting experience, keywords and using AI plugins.

I was ready for a final battle!

✓ No CEO experience that scares recruiters.

✓ No C-level. Only product leadership and consistent growth.

🔗 Feel free to check the list of vacancies.

➞ I decided to apply to the selected 100 positions and use a very thoughtful and individual approach — sometimes even more than needed.

➞ As advised, to focus on One Thing, I downgraded to the Head of Product and even Product Manager.

➞ On average, I spent 30–60 minutes reading, understanding and semi-manually tailoring my CV and deck to every job description.

➞ I studied the company’s products and profiles, used AI to help me with skill matching.

➞ I did my best not only by applying with a CV but also by adding a cover letter and deck and reaching out to the hiring manager.

➞ I implemented every reasonable advice I received from the audience, career coaches, Instagram gurus or anonymous experts in comments.

➞ I changed fonts, sizes, and keywords, used AI plugins, rephrased sentences, used referrals, did networking, wrote cover letters, etc… I applied on 6 different platforms and directly contacted recruiting agencies and recruiters.

This approach first demonstrated immediate conversion into interviews but eventually ended up with the following results:

Things I learned actually made the whole process pointless.

There’s almost no chance of meeting all the ridiculous limitations and criteria recruiters and hiring managers put in job descriptions.

Let’s take a closer look:

1. CARV — a smart device for skiers. Rejected me for the position of VP of Product because I have 10 years of snowboarding, but not skiing. And my experience is “a little irrelevant to the hardware startup”

I checked the profile of their Senior Product Manager and found no trace of previous hardware experience. But there’s no point to argue.

2. My story was widely known, so people at my fiancée’s work wanted to help, too. One of them referred me to Founder’s Factory. The early-stage incubator matches technical and non-technical founders to work on promising ideas.

I saw the position, and it was an absolutely perfect fit!

Co-Founder of the Fintech Studio. OMG! Leadership position, fintech, venture building, accelerator. I was excited! I wrote a reference mail, created a deck and a mind map, and prepared for the meeting. I was so excited and couldn’t wait to hear the feedback from the hiring manager.

It was an obvious match.

Guess what happened.

No one even looked at my files.

The hiring manager told me:

– oh, sorry, you know, the venture team decided we need someone with HealthTech experience and family in India. We decided to target the Indian market first. Yeah, we added this at the last moment, so it’s not in the original job description… Good luck!

And so on. First, companies put very general and vague job descriptions almost everyone could fit, secondary you got automatic rejection.

A crumble of feedback I was able to get:

– “We have candidates with hospitality & commercial prop experience”

– “The client has been very specific regarding the exact experience across Product leadership in high-growth (early to mid-stage) consumer tech and will reject anyone who doesn’t match”

– “Unfortunately, you’re not quite right for this role”

So

– You should focus on one area and show specialisation and experience. Done

– You should humble yourself and start from a lower position. Done

– You should thoughtfully pick positions and not mass apply. Done

– You should tailor your CV to every position to match keywords and your experience with JD. Done

– You should add additional materials, portfolio, and cover letters and reach out to hiring managers. Done

100 applications, 5 interviews, 26 rejections, 70 ignored.

(just a note to everyone who’s just joined. It’s 100 applications on top of the previous 1001)

So, what insights did I gain? Which data was collected? What happened next?

👉 🔗 Continue to Part 2 — The Recruiting is broken