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May 4, 2026, 2:10 p.m.
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How to Stand Out in an AI-Driven Job Market: Tips from Kristina Simmons

Brief news summary

AI is rapidly changing the job application process, enabling candidates to tailor résumés, mass-apply to roles, and even bluff interviews, making it tougher to stand out. Kristina Simmons, former partner at Andreessen Horowitz and current head of Overwater Ventures, warns against overreliance on AI in job hunting. She emphasizes the importance of genuine communication, saying, "You can't fake heart. You can't fake grit." To stand out, Simmons suggests becoming visible to employers by attending events or engaging thoughtfully on social media to attract their attention. She encourages candidates to use AI as a research and creative tool—such as exploring industry insights or crafting impressive application materials—but cautions against using AI to replace authentic human interaction during interviews. The passion, energy, and personal tone conveyed in interviews are irreplaceable and key to demonstrating one’s true self beyond technology.

AI is rapidly changing the job application process. Applicants can now use this technology to customize their résumés, apply to hundreds of roles at once, and even bluff their way through interviews, making it feel increasingly difficult to distinguish oneself. Kristina Simmons, formerly a partner at Andreessen Horowitz, then chief of staff at Vinod Khosla's venture capital firm Khosla Ventures, and now running her own firm, Overwater Ventures, warns against over-reliance on AI during job searches. When hiring and interviewing, Simmons looks for candidates who communicate with genuine passion. “You can't fake heart. You can't fake grit, ” she told Business Insider. Here’s how Simmons advises candidates to stand out in today’s AI-saturated job market: Become visible to potential employers If you want to work at a company and the CEO is speaking at an event, attending in person and introducing yourself is one way to get noticed, Simmons said. Share which role you’ve applied for and why you’re interested. Alternatively, if the CEO is active on X (formerly Twitter), responding to their posts with thoughtful insights can help. “Make them want you, rather than the other way around, ” she added. Leverage available tools Simmons advocates using all tools at your disposal — including AI — in your job hunt. She noted that if AI had existed when she interviewed for A16z, she would have used it to research the company and her interviewers. AI can also assist in mapping out your career trajectory.

For instance, you can ask AI about top companies in women’s health to guide your research into entering that sector. Use AI to boost creativity Candidates can harness AI to quickly produce creative materials, like a polished presentation highlighting why they’re an excellent fit. They might also propose innovative ways to use AI in the role they’re pursuing. “I had a candidate who wanted to join Overwater and said, ‘Here’s how I would apply AI across your firm. This is me doing the job before I have it, ’ which was an intriguing way to use new tools to pitch for the job, ” Simmons explained. However, Simmons cautions against relying on AI for everything, especially during interviews. “The best part of interviewing is showing that you're human, which technology can’t replicate. That comes through in your passion, energy, and tone. You can’t fake that, ” she said.


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