AI-Powered Job Search: An AI/ML Recruiter's Real-World Guide

TL;DR: AI/ML hiring expert Jassi Starleaf reveals why recruiters can tell everyone's using AI—and why that's actually okay. The key isn't hiding AI usage, but using it strategically to personalize applications with specific examples and metrics. With 500+ applicants per role becoming the norm, she shares real-world tactics for timing, networking, and standing out in an AI-saturated market.

Jassi Starleaf, a Senior Talent Partner at Learneo with over seven years of full-cycle recruiting expertise specializing in AI and machine learning engineering, research and data science roles, recently joined us for Wellfound's Ask a Recruiter series to tackle one of 2025's biggest career questions: How do you strategically leverage AI in your job search without undermining your authenticity?

Having successfully scaled global engineering and technical teams from zero to one across North America, Europe, and Asia for high-growth startups from Series A to C funding, Jassi brings a recruiter's insider perspective on AI's transformative impact on talent acquisition. Known for solving "troubled" and hard-to-fill positions at companies like Course Hero and QuillBot, she's seen firsthand how the job market has evolved—and where candidates are getting it wrong.

The Reality Check: Everyone's Using AI (And That's Fine)

"As a recruiter, I can tell everyone's using AI nowadays. So it's okay. And you don't have to shy away that you're leveraging AI."

Jassi opened with this reality check, immediately addressing the elephant in the room that's been stressing out job seekers everywhere.

The game has fundamentally changed. With employers now receiving hundreds of applications within hours of posting a role, the old "one resume fits all" approach is dead.

"Employers are receiving multiple candidates that are applying to one specific job. So in this critical time period, you're wondering, how do I stand out as a candidate among the thousands of other applicants?"

But here's the twist: The solution isn't to avoid AI—it's to use it smarter.

Use AI as Your Collaborator, Not Your Copywriter

The biggest mistake Jassi sees? Candidates treating AI like a magic copy-paste solution rather than an intelligent collaborating partner.

"Use it as a collaborator but not as a copy and paste solution. Use it as like a guiding point and find out what are the keywords that you need to use, leverage those keywords and then also justify your experience based on those keywords."

Here's her recommended workflow:

Feed AI tools the job description and ask for keyword identification
Brainstorm all your relevant projects and experiences
Use AI to help narrow down to the top three most relevant examples
Have AI help structure compelling bullet points—then add your personal metrics and outcomes

The key difference?

"Give specific examples why your results are oriented. So that's one of the things, if AI is recommending certain keywords and it sounds really vague, I would tweak it to something that sounds more like you and authentic."

The New Application Strategy: Speed + Personalization + Connection

With the market saturated by AI-generated applications, Jassi shared a three-stage strategy that actually works:

Stage 1: Apply Fast and Smart

"Within the first week of taking applicants, we've already probably narrowed down the list of people."

Jassi revealed why timing is everything. Set up job alerts across multiple platforms and apply within the first 24 hours.

Tools like Wellfound's saved job alerts and our beta product Raven can help you quickly identify the best-fitting opportunities so you can apply within that crucial first 24-hour window

"You're one of the first 100 candidates or so that have applied within four hours or so. So that's one strategy."

Stage 2: Connect After Applying

This is where most candidates stop—and where you can differentiate yourself.

"Now find out who do you already know with that company? Maybe you may know someone that someone else knows at this company that is willing to refer you."

Jassi's networking script: Find the hiring manager, recruiter, or team member and send a short message like:

"Hi, I just applied for the [position] and I'm really excited about the opportunity to work on your team. What stood out to me in the job description was [specific detail], which aligns perfectly with my background in X, Y, and Z."

Why this works:

"That humanizes your application and that touch point... And that's something that AI won't be able to do for you. And that shows, this is actually a real person that reached out to me."

Stage 3: Keep Moving

"I wouldn't get too fixated on this one specific company... And you've done everything you can at the end of the day."

Use tools to track similar roles at similar companies rather than putting all your hopes on one application.

Cover Letters: Quality Over Quantity

When asked about AI-generated cover letters, Jassi's take was refreshingly practical:

"I have seen a lot of resumes that I can tell it's written by AI because they're not giving me specific examples."

Her advice: Only write a cover letter if you can add genuine value beyond your resume.

"If you really, really want this job and you really want to stand out, leverage your own story, metrics, and examples for the cover letter versus just using a vague [blanket] one that just comes from an AI tool."

Navigating AI's Impact on New Graduates

For recent graduates worried about AI replacing entry-level opportunities, Jassi offered a reality check and a roadmap.

"AI is actually going to change a lot of new jobs, and also create new jobs."

The skills that will always matter:

Social and emotional intelligence: How you communicate, collaborate, and build relationships
Higher cognitive skills: Complex problem solving, critical thinking, and creativity
Tech fluency: Understanding how to work alongside AI systems, not just use them

Her advice for new grads centers on embracing calculated risks early in your career. Jassi shared her own experience to illustrate this point:

"When I started out in my career, I was working at a law firm as a legal secretary and an admin. I remember they were paying me really well, but I took this pay cut. I joined a HR rotational internship program and it was paying minimum wage at the time. I took a risk in my career, but at this point I was willing to take a risk because I really wanted to get into HR and into recruitment."

That career pivot ultimately led to her current role as a senior AI/ML recruiter. Her takeaway:

"Be willing to take risks early on in your career because as you get older or as you advance in your career, it's gonna be harder to take risks."

Salary Negotiation in the AI Era

AI has democratized salary research, and Jassi encourages candidates to take advantage. She recommended leveraging tools like Wellfound's salary calculator, levels.fyi, Glassdoor, and Blind for market data, while using AI to practice negotiation scripts.

"Practice negotiation scripts. So that's something you can definitely leverage AI for... you can rehearse tricky conversations, [asking] how do I respond to this if they ask me this specific question?"

For non-salary negotiations (like vacation time):

"Vacation is something that could be often more negotiable than the base salary. And it's less costly for the company."

Be transparent about your needs early in the process.

The Recruiter's Reality: Volume Is Overwhelming

Jassi didn't sugarcoat the current market reality:

"It's a very competitive market. I am overwhelmed as a recruiter. Honestly, I'm spending more hours working because, honestly, it's really hard being a recruiter right now because you're not able to help everyone."

What gets her attention?

"I actually prioritize candidates that actually email me as a recruiter ...they found my email ...they actually did their extra homework... or they reached out to someone in the company and they're sending me a referral."

The bottom line: In a market flooded with AI-generated applications, the candidates who stand out are those who do the human work that AI can't replicate—research, genuine outreach, and building real connections.

Actionable Takeaways

Set up job alerts across multiple platforms and apply within 24 hours of posting for maximum visibility
Use AI tools like Claude or ChatGPT to identify keywords and structure responses, but always add specific metrics and personal examples
After applying, find and message someone at the company (hiring manager, recruiter, or team member) with a brief, genuine note about your interest
Join industry-specific communities and attend networking events where job opportunities are often shared before public posting
Practice salary negotiation conversations with AI and research compensation using tools like Wellfound's salary calculator before interviews

This article summarizes key points from Wellfound's 'Ask a Recruiter' live Q&A event featuring Jassi Starleaf, Senior Talent Partner at Learneo. To find out more candidate tips, check out other 'Ask a Recruiter' sessions on the YouTube playlist here.