7 Weeks. 3 Offers.
READ TIME: 5 MINUTES
Seven weeks. Five companies. Three offers.
That's where Chris ended up.
Here's where he started.
For a decade, Chris never had to look for a job. His network brought opportunities to him. In 2025, he decided to run a real search. One that was deliberate, intentional, on his terms.
He submitted applications. He customized his resume. He thought he'd cracked the ATS.
Silence.
He turned to AI. Tried every angle he could think of. Refined his prompts. Resubmitted.
He got a few interviews. But nothing progressed.
Two months in, he was questioning whether to leave EdTech entirely. He wondered if that was preventing him from landing interviews. Leaving would mean stepping back on comp and responsibilities.
Then he saw my post on LinkedIn.
One conversation changed everything.
After our free consult, Chris told me he'd learned more in that one hour than in the two months he'd spent grinding on his own.
He left the call with one conclusion: it was time to stop investing only time.
His words: even if that means skipping some coffees out.
Here's what AI missed.
After months of customization, Chris's resume was still missing the fundamentals. The things a hiring manager looks for:
What type of product he sold
How many people he managed
The promotions he'd earned across companies
The actual impact of his work
AI can help you optimize what's there.
It can't add what isn't.
It doesn’t know your story.
It doesn’t know what the hiring manager is looking for.
We fixed it. The market responded immediately.
Chris's background covered both IC and management, AE, SE, and manager roles. He had things he loved about each. Instead of forcing one path, we built a hybrid approach: two targeted resumes, one toward AE and one toward management, and rebuilt his LinkedIn to attract the right recruiters for both.
The same week we made the changes, recruiters started coming to him.
From there, we shifted focus to his network. Between warm outreach and recruiter inbounds, Chris moved into active conversations with five companies.
Three of them became offers.
Then came the biggest negotiation of his career.
My daughter was due that week. She came five days late, which turned out to be exactly what we needed. Every one of those days we were back and forth with both companies, using competing offers and market data to push the number higher.
The day she was born was the day Chris signed.
I asked him what the hardest part had really been.
Not the applications. Not the interviews.
The weight of it.
"It's your whole life. Your career identity, the financial implications. All of it. There's this feeling of doubt, fear, and stress from the uncertainty. The question was always: how long is this going to take?"
"When I started working with you, that doubt went away. Not because I had an offer because I had immediate little signs that the changes were paying off. I knew I'd land where I needed to be."
He thought three to six months.
It took just under seven weeks.
I asked what a coach gave him that AI couldn't.
"AI struggled to give me what I needed, even when I prompted it well. The support, the personal guidance, your individual experience. That's what made the difference."
"Career coaching is fundamentally a human service."
"It's an investment. You might have to sacrifice spending in other areas. It will impact your short-term cash flow. But it will pay off."
That’s Chris’s story.
I want to hear yours.
Hit reply and tell me: What's the part of your job search that feels most uncertain right now? I read every response.
To clarity and confidence in your career path,
Amanda
See you next Sunday.
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