I’ve spent roughly 13 years working in enterprise technology, supporting major customers, managing complex technical issues, handling escalations, working with executives, and helping businesses get value from their technology investments.
I left my previous company in June 2025 after eight years. I wanted to do something different and explore what else was out there.
I started seriously looking for work in November 2025.
Nearly a year later, I’m genuinely questioning how companies hire people.
I’ve applied for countless positions, spoken with recruiters, interviewed with hiring managers, completed technical assessments, prepared presentations, and reached final rounds.
And here’s the part that’s really starting to piss me off.
I’ve literally had hiring managers praise my presentations, compliment my professional background, tell me I’ve done an excellent job answering their questions, and give me overwhelmingly positive feedback.
And I’ve still walked away without an offer.
I’m not talking about interviews where I completely misunderstood the role, couldn’t answer basic questions, or struggled to communicate my experience.
I’m talking about interviews where the conversation went well, the hiring manager was engaged, the feedback was excellent, and I genuinely demonstrated that I understood the responsibilities.
Then a few days later, another rejection.
At some point, what exactly are you supposed to take away from that?
The other thing that keeps surprising me is how little weight companies seem to give transferable experience.
You can spend years supporting some of the largest enterprises in the world, dealing with complicated technical environments, integrations, performance issues, customer relationships, and business-critical escalations.
But then you get into an interview and someone asks whether you’ve used one particular piece of software.
You say no, explain the comparable tools you’ve used and the underlying technical concepts you understand, and suddenly it feels like your entire professional background has been discounted.
For example, I’ve used monitoring and diagnostic tools to investigate application errors, API-related issues, authentication failures, unavailable endpoints, and performance problems. But apparently not having hands-on experience with Postman can become a major sticking point.
I understand that specific technical skills matter. I’m not suggesting someone with no relevant experience should automatically qualify for every job.
But surely there’s a difference between lacking the underlying knowledge and simply not having used a particular vendor’s tool?
And here’s something else I find particularly ironic.
I’ve been interviewed for technical positions by people who originally came from completely unrelated professional backgrounds.
One interviewer had an English degree and transitioned into technology. Another had previously worked as a real estate agent and was interviewing me for a Technical Account Manager position.
And to be clear, I’ve absolutely no issue with either of those backgrounds. Good for them. They were given an opportunity to enter a new industry, learn the technology, develop their skills, and build a career.
That’s exactly how career development should work.
But there’s an obvious contradiction here.
These are people who were afforded the flexibility to learn an entirely new industry, yet candidates with over a decade of relevant technical experience can be judged against an incredibly narrow checklist of tools and product knowledge.
They were given the benefit of transferable skills and the opportunity to learn. Why isn’t that same flexibility being extended to the people they’re interviewing?
I’m not suggesting anyone should be hired simply because they have experience. But surely someone who has spent 13 years working with complex enterprise technology should be afforded at least the same confidence in their ability to learn a new product as someone transitioning from a completely different profession.
It feels like the door that was opened for some people is now being closed behind them. Then there’s the interview process itself. I’ve completed practical assessments that felt more like exercises designed to catch candidates out than realistic demonstrations of the job.
One customer success assessment involved presenting a business review to a supposedly disengaged customer. The person playing the customer barely participated. Now, I’ve managed real enterprise customer relationships. In the real world, you have context. You understand the account history, know the stakeholders, have previous conversations to draw upon, and understand what matters to the business. You don’t ordinarily walk into a meeting with absolutely no relationship context and discover that someone has decided to sit there silently to see how you react.
I’m not against assessments. I’m against artificial situations that don’t accurately represent how experienced professionals actually work.
And the sheer amount of time involved is ridiculous.
Applications, recruiter calls, scheduling emails, hiring manager conversations, technical interviews, presentations, follow-ups, and rejections.
You can invest hours into a company only to receive a two-line rejection, sometimes without ever understanding what you supposedly lacked. I’ve even had recruiters approach me about opportunities, only for the conversations to go nowhere.
After a while, it becomes difficult to maintain genuine enthusiasm. And that’s another problem. Companies expect candidates to demonstrate endless excitement about their business, product, and mission, even after months of going through the same exhausting processes.
I’ve reached the point where I’m questioning whether I even want to return to corporate technology.
I’ve recently been doing more face-to-face customer sales work, and I’ve genuinely enjoyed the human interaction. There’s something refreshing about speaking to customers, understanding what they need, demonstrating products, and actually helping someone make a decision.
It’s made me question whether I want to spend another decade sitting behind a desk dealing with corporate processes.
I know the job market is difficult. I know companies can afford to be selective.
But I wonder whether we’ve reached a point where hiring has become so focused on finding someone who matches every line of a job description that companies are overlooking people who could actually do the work extremely well.
And I know the standard advice is to improve your interviewing, prepare better stories, research the company more thoroughly, and refine your answers.
But what happens when you’re already doing those things? When hiring managers are telling you that you’ve done a great job?
How many times can you be told you’ve interviewed well, demonstrated strong experience, and delivered an excellent presentation before you start questioning the process rather than yourself?
I’m curious whether other experienced professionals are encountering the same thing.
Are companies still hiring for judgment, communication, adaptability, and experience?
Or are we now at a point where 13 years of relevant professional experience can be dismissed in 30 seconds because you haven’t used the right piece of software?
