Application Strategy: Scale from 2 applications per day to 2 interviews per week with ChatGP
“When I started using this, I started getting about two interviews a week with actual live people.”
For nearly a year, Casey (name changed for privacy) had been working toward a career change and applying for roles without getting the traction he wanted. He was transitioning his background as a librarian into an adjacent field: Learning & Development (L&D).
For months, Casey said he was “getting nowhere.” Maybe he'd make it through an initial screen, and then... crickets. He spent hours tailoring resumes and cover letters, managing only 1-2 applications per day.
The lack of response started affecting how he saw himself, believing, "I am hopeless in this." But then, he realized something important.
“I'm not unqualified. I did not get a useless degree. It is the system that's been instituted where all of these difficulties are coming from.” - Casey
He needed to find a different way to work within that system... and that's when he started experimenting more seriously with ChatGPT.
Over the course of a month, he had developed a process to apply for 10-15 roles per day and now averages two live interviews per week.
Casey's 5-Step ChatGPT Job Search Process
Casey got clear on his story & qualifications.
When we worked together one-on-one, Casey and I clarified what he was targeting. Then, we optimized his resume and overhauled his LinkedIn to better represent his relevant and transferable skills as a candidate.
"I've based a lot of this on my LinkedIn profile and the resumes that you did for me and helped me do." - Casey
He did NOT apply for every role.
Casey found LinkedIn Premium particularly useful in sourcing roles of interest, as it highlighted which roles were a strong match based on his preferences and LinkedIn Profile.
He shared past versions of his resumes, cover letters, and application essay answers with ChatGPT to train it on his work experience.
Instead of immediately telling it to "write me a resume for this job," Casey's first prompt was, "Am I actually a good fit for this job?"
ChatGPT would then compare the posting with his real work history and help identify 1) where he was a strong match, 2) where he had transferable experience,
3) and, just as importantly, where he had genuine gaps.
If the job looked promising, then he'd prepare to apply.
He used ChatGPT to know what employers were looking for.
ChatGPT could then tailor his resume, cover letter, and application essay answers based off of the most relevant parts of his story. Then, Casey could review, edit, and apply quickly.
For one job, his experience managing learning content was prioritized.
Another role called for work in accessibility.
For a learning design position at a bank, ChatGPT even recognized that Casey's banking experience from almost 20 years ago now differentiated him as a candidate.
ChatGPT was surprisingly good at looking across your experience and asking, 'Which evidence matters for this particular employer?' It didn't invent 30 different versions of me... They're all based on the same person and the same employment history: me."
Increasing application volume has also been crucial.
Casey went from applying to roughly one or two jobs per day to 10–15, while still tailoring the materials. That's when he started consistently landing two interviews per week with actual people.
ChatGPT now helps with other parts of the search.
ChatGPT has also helped Casey identify what salary range he should target based on his experience and which types of interview questions he is likely to encounter. It also gave him key points to highlight in his 60-second introduction, “Tell me about yourself,” and thank-you emails.
He's even used it to prepare for a Loom video application and create a professional headshot for his LinkedIn.
Ultimately, AI can save job seekers "time and heartbreak."
Casey recognized that the system was broken, not him. He told me that the ghosting and rejection stop feeling so personal when you recognize how much of the job search today is a numbers' game.
He now describes his workflow as:
Job posting → fit analysis → resume → cover letter → application questions → salary → interview preparation.
He's used this method to tailor over 20 resumes and cover letters, but still reviews and edits drafts to make sure they sound like him.
What's important here is that "ChatGPT doesn't manufacture an impressive candidate. It helps translate your experience in terms the employer is actively looking for."
Watch the full recorded interview on Career Crossings.
Join Career Crossings to watch Casey share more about his journey and walk through each of his prompts and process.
You'll also be able to connect with him to ask questions about what worked, what didn't, and how he's continuing to refine his process.
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