This former VP of product has applied to more than 1,500 jobs. He says it's hard to see the toll it has taken on his kids.

"I joined my last company as a director of product, and within a couple of months, I had been promoted to the VP of product. Then, a couple of months later, that company almost went out of business. They had to downsize and kept me and one other person on. I was very thankful, as they laid off the rest of the company and tried to restart. We really gave it the old college try, but we weren't getting the traction we needed."

"I thought it was an opportunity because I saw that AI was going to change everything. I had done enough with it over the years that I knew there was going to be some serious opportunity there. I thought if I could go in and get really educated on this stuff - because it's moving so quickly - and combine that with my experience, I was going to be in really good shape."

"Even though I've applied to over 1,500 jobs in the past 15 months, I've been hyper-focused on jobs that I thought I was a good fit for - not just spray and pray. You find a role that you're perfect for that was posted three days ago, and it says over 1,000 applicants. It's like, "OK, I'll submit my résumé and reach out on LinkedIn to whoever I think the hiring manager is." But, more times than not, I get no response."

Jacob Woodward, 44, married father of six in Grand Island, New York, has been looking for a job since July 2024 after leaving a startup where he rose from director to VP of product. His company nearly collapsed, downsized, and he later resigned to pursue opportunities in AI, believing his experience plus rapid AI learning would position him well. He has applied to over 1,500 roles in 15 months, focusing on fits rather than mass submissions, and often finds listings with more than 1,000 applicants. He has received few responses despite outreach, experienced a verbal offer that fell through, and remains unsure about next steps, including relocating.

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