How AI Can Hurt Your Job Hunt, According to a Tech CEO

Pedestrians cross The Embarcadero to the Ferry Building on Jan. 15, 2025 in San Francisco.

The Job Market Is Changing Fast

The job landscape, particularly in tech-centric areas like the Bay Area, is undergoing a radical transformation. With artificial intelligence (AI) increasingly taking on roles traditionally held by entry-level employees, competition for available jobs has intensified. In June alone, U.S. job openings dropped to 7.4 million from 7.7 million the previous month, making it harder than ever to land interviews. On average, candidates now need to submit 42 applications just to get a single interview opportunity.

As a co-founder of Treet, a San Francisco-based resale tech startup, I’ve observed these shifts firsthand. Rather than hiring a new engineer, we opted to invest in AI tools that help our existing team accomplish more. This decision may have been efficient, but it also meant one fewer job opening in a city where opportunities are already scarce.

AI Tools Are a Double-Edged Sword

In this competitive environment, it’s no surprise that job seekers are turning to AI tools like ChatGPT for assistance. The instinct to gain an edge is understandable, but many are using these tools in ways that actually hinder their prospects. At Treet, every time we post a job opening, we receive numerous cover letters that are nearly identical—perfectly formatted, lengthy, and devoid of personality.

It’s clear what’s happening: candidates are feeding job descriptions and résumés into AI systems and asking them to generate customized cover letters. While this might seem like a clever shortcut, it often backfires. Instead of showing initiative and authenticity, these AI-crafted messages come across as impersonal and lazy. Ironically, a cover letter with a few typos written from the heart often makes a stronger impression.

Even AI Companies Are Cautious

Interestingly, even major AI firms discourage reliance on AI during job applications. Anthropic, a leading AI company, has explicitly advised applicants not to use AI tools in their interviews. The company wants to gauge genuine interest and assess communication skills that aren’t AI-assisted. This reinforces the idea that while AI can be helpful, it shouldn’t replace human effort and authenticity in the hiring process.

AI Should Assist, Not Replace

Using AI effectively is all about balance. It’s one thing to use it to check grammar or brainstorm ideas; it’s another to let it do all the work. Once a candidate secures an interview—AI-assisted or not—the next challenge is proving their skills are real. Because of AI’s growing influence, many employers are moving away from take-home assignments, which can easily be completed with AI. Instead, they’re favoring real-time assessments that better evaluate true capabilities.

This shift is happening in education as well. Professors are moving back to in-class essay writing to ensure students actually understand the material. The parallels in the job market are clear: authenticity and real-time performance are becoming more important than ever.

Sales and Communication in the AI Era

At Treet, we’ve seen this dynamic play out on our sales team. Our top-performing sales reps use AI as a tool to refine their messaging, not to generate it entirely. Clients are increasingly wary of messages that sound robotic or overly polished. The best sales emails are casual, succinct, and genuinely human.

When training new sales hires, we emphasize the importance of sounding natural. Many new grads tend to write “professional” emails that resemble college essays—perfectly structured, grammatically flawless, and completely impersonal. These messages often miss the mark. For example, any email that begins with “Dear Mr. Disraeli” is likely headed straight to the trash. People want to connect with people, not with bots.

Authenticity Is Your Best Asset

The takeaway is simple: use AI to enhance your communication, not to replace it. Crafting messages that sound human—even if that means including a small typo—can make a big difference. It shows you care enough to personalize your application and that you’re capable of authentic communication. That’s what employers are really looking for.

Yes, the job market is tough. But that doesn’t mean job seekers should blindly rely on technology. Instead, they should focus on using AI thoughtfully, as a tool to refine—not define—their voice. By doing so, they stand a much better chance of connecting with employers and landing the roles they desire.


This article is inspired by content from Original Source. It has been rephrased for originality. Images are credited to the original source.

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