"Well, Joe, I did it. I applied to all the jobs."
That’s how Sam opened our conversation—and I couldn’t help but laugh.
Let me give you a little background.
Sam is a former VP of Product who climbed the ladder from project management. She was laid off about five months ago and, since then, has been treating her job search like a full-time job. And I don’t mean casually poking around LinkedIn—I mean intense, tactical, organized execution. She’s not a developer, but she knows how to connect every piece of the development pipeline—from Agile and QA to infrastructure and delivery.
Ask her what her superpower is, and she’ll tell you: execution. Not ideas. Just getting sh*t done. With extreme precision.
So when Sam decided it was time to find a new role, she went all in. No hesitation. No distractions. Just total focus on one goal: getting herself into a new seat.
(She even talks about herself in the third person sometimes.)
But here’s the twist: After six months of relentless hustle—over 500 applications, dozens of interviews, and endless networking—she hit a wall. There were no more jobs left to apply for. She’d exhausted every opportunity she was remotely qualified for.
So she texted me and asked if I wanted to grab coffee.
What followed was one of the realest, most eye-opening conversations I’ve had about the job market in 2025. Here's what Sam learned from the front lines:
1. “The ATS-Friendly Résumé Thing Is Bullsh*t”
Her words, not mine—but I agree.
Like most job seekers, Sam started by tailoring her résumé to be ATS-friendly (that’s the applicant tracking system that screens résumés using algorithms). It made sense—especially since her former company had recently adopted AI-based screening.
But after weeks of tailoring keywords and formatting, she realized something: it wasn’t working. The responses she got were mostly from companies she didn’t want to work for—low-paying, low-culture gigs that weren’t a fit.
Worse, the interviews that followed were mostly surface-level “vibe checks” with junior HR reps that rarely led anywhere.
So she changed her approach. Instead of trying to game the bots, she rewrote her résumé to speak directly to the kind of hiring manager she’d want to work for. That shift made a difference. She started seeing more meaningful traction.
2. There’s Nothing in the Middle
With nearly 20 years of experience, Sam cast a wide net—applying to roles from mid-level (5+ years) to VP-level leadership roles.
But she noticed something strange: there’s very little in the “middle” anymore.
The market is flooded with roles just above entry-level—companies wanting experienced (but cheap) talent. And at the other end, there are leadership roles that look good on paper, but often quietly expect you to double as a full-time salesperson or revenue driver.
The result? A job market split between labor and sales. Middle management? Ops experts? Process people? They're getting squeezed.
3. “AI Jobs” Are Often Smoke and Mirrors
At first, Sam avoided applying to anything labeled “AI-related,” assuming she didn’t have the right technical background.
But curiosity got the best of her. After reading a few job descriptions, she realized something hilarious: a lot of “AI jobs” just want someone who knows how to use ChatGPT.
“I figured, well, I can use ChatGPT… so I applied,” she said. And it worked—she started getting bites.
Turns out, unless you’re building AI itself (think: machine learning PhDs), most “AI” roles are just regular jobs wrapped in buzzwords.
4. Salaries Are Dropping
This part hurts. According to Sam, the same roles she was looking at six months ago were paying $250K–$300K. Now? They’re closer to $180K–$220K.
It’s the result of two things: uncertainty on the employer side, and desperation on the job seeker side. Companies know candidates are hungry. And candidates are starting to lower expectations just to get back in the game.
5. Big Company Experience Matters—A Lot
Even though Sam’s most recent work was at a mid-sized startup (under $50M in revenue), interviewers kept steering the conversation back to her time at a major tech company years ago.
“I did a stint,” she shrugged. “Didn’t change the world, but it comes up every time.”
There’s a clear bias right now for people who’ve been through the wringer at big, well-known companies. It’s like a stamp of credibility—sometimes more important than recent accomplishments.
6. Private Equity and Investors Are Heavily Involved
Sam told me about three hiring processes that went smoothly—until the very end. Right before the offer, someone new would suddenly appear. A “random guy.” Often from private equity.
And then—wham. The offer would disappear.
She asked, “Is that a thing?”
Yeah, it’s a thing. I’ve even been that “random guy” before. Investors are getting more involved in hiring—not just at the executive level, but deeper into the org chart. They’re being asked to vet candidates, slow down offers, or rethink roles entirely.
7. The Common Thread? No Confidence
Sam and I talked for a long time. If I had to sum it all up in one theme, it’s this: there’s no confidence.
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No confidence in résumé screening systems
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No confidence in hiring processes
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No confidence in how to structure teams
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No confidence in what roles are actually needed
It’s like the whole hiring ecosystem is stuck in a fog. And that uncertainty is bleeding into everything—from the job descriptions, to the interviews, to the offers that never quite arrive.
Where Does That Leave Us?
Sam told me something that stuck with me:
“One morning last week, I opened my laptop and realized I had nothing to do. I’d applied to every job. I was totally up to date on my pipeline. And it scared me.”
But the story doesn’t end there. A few days later, she texted me again—this time with better news. New jobs were starting to pop up. Her network was getting more active. Conversations were picking up again.
Maybe we’re about to see another wave.
I hope so. For Sam. For all the Sams out there. And for the companies that need people like her.
If you’ve ever been in the job search trenches, you know how exhausting it can be. But there’s still value in sharing the war stories. So if you want to keep hearing from folks like Sam—and from me—join the newsletter and let’s figure it out together.
— Joe Procopio