🚨 365 Days of Stories: Day 44 – The Quiet Struggle of Job Hunting in Tech Leadership
Over the past two years, I’ve stepped into the job market a few times.
Each time, I gave it 2–3 weeks. And each time, I stepped back — not because I wasn’t good enough… But because I realised the process wasn’t built for someone like me.
Let me explain.
🧭 I left my last role in tech leadership with no plans of going back. I wanted to build. To create. To chase something meaningful in life.
And I did. I started ElevateIdea and poured myself into it.
But like any entrepreneurial journey, there were highs and lows. During the tougher patches, I’d ask:
“Is there something meaningful I can be part of — Where I can help take a business from 1 to 10?”
Because maybe 0 to 1 wasn’t working for me right then.
So I’d test the job market — hoping for a great opportunity.
But what I found was a system that didn’t know what to do with people like me.
🛠️ Let’s be honest — job hunting for senior roles is a different game.
There are only three common paths:
🔹 Apply online — and see 1000+ applicants within a day. Most leadership roles get filled internally or through referrals. The posting? Often just a formality.
🔹 Reach out to your network — and hear the same thing: “Hiring freeze.” “Only niche AI/data/cloud roles are open.”
🔹 Wait for consultants — who rarely call for real leadership roles. It’s usually mid-level manager roles in smaller firms.
🧪 I even tried a more direct approach.
It’s easy to guess the hiring manager in smaller to mid-sized companies. If a VP role is open, it likely reports to the CTO/CEO.
So I reached out — direct, thoughtful messages. But mostly, I got polite replies like:
“Please apply on our careers page.”
No dialogue. No curiosity. No interest in what someone experienced might bring.
⚠️ That’s when I paused and asked:
“If I’m doing all this and still not converting — is this about me, or the system?”
Here’s what I’ve realised:
1️⃣ Tech isn’t growing like it used to. It’s been 3–4 years of stagnation. Companies are cautious, not ambitious.
2️⃣ AI has shifted the game. Work once done by teams is now handled by tools. Hiring managers want specialists — not broad leaders.
3️⃣ Leadership roles rarely go public. They’re filled via internal moves or warm intros.
So yes, I’ve paused my job search every time. Not because I gave up — But because I got frustrated with the experience.
Endless hunting. No responses.
It’s nearly impossible to find something meaningful in this crowded market. Not when most roles are either closed or transactional.
I wasn’t chasing a title. I was looking for impact.
And when I couldn’t find it?
I’d go back to ElevateIdea — Back to building the kind of work I was searching for all along.
💬 If you’re a senior leader navigating the same confusion — know that you’re not alone. This isn’t a failure. It’s a moment of reflection in a changing world.
Let’s connect.👇
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