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Courtney Clapper started applying for jobs in 2025 after graduating from Cornell Tech.
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He tried video cover letters, portfolios, and more to stand out, but had no luck.
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A hack on Reddit helped him connect with hiring managers and landed him a top strategy job.
This essay is based on a conversation with Courtney Clapper, a 32-year-old strategy lead for a major retailer in New York. It has been edited for length and clarity.
I started looking for a job in the fall of 2025, a few months after receiving my MBA from Cornell Tech. I was applying for a mix of roles, such as product manager or digital strategist, and I knew the competition would be fierce in this tough job market.
From portfolios to video cover letters, I tried all kinds of creative methods to make my personality stand out and show, but they just didn’t work. A simple, free AI tool that discovered the emails of hiring managers landed me several interviews — and a job.
Video cover letters were a great start for me
My first thought process when entering the job market was to imagine myself as a recruiter, being slammed with thousands of resumes full of data and numbers.
I thought it would be in my best interest to tell them what makes me different: my personality. So, I recorded myself reading my AI-written cover letters, threw in a joke or two, and attached the video via a private YouTube link.
The video tells recruiters that I can speak and present well, and it gives them a sense of who I am. This approach helped me land an interview at Microsoft. They specifically called out the video, saying that it made them feel like they already knew me, which I thought was a great response.
I still wanted to try different creative ideas.
Next, I decided to make something more visual – a portfolio
My portfolio was in the form of a timeline. It included pictures of all the professional endeavors I thought might help land me a job, from products I built and pictures of my time pitching at Cornell. My goal was to create something more visually interesting to showcase my skill set and personality.
I’d also heard of people getting jobs putting together a slideshow about how to improve the company, so I gave it a shot, and it didn’t really get me anywhere. None of these strategies were worth the time commitment they required.
Even referrals got me nowhere. I have a solid network, and it didn’t make a difference. Interestingly, I applied for several roles at Microsoft, and I only got one interview for which I did not have a referral.
I came across a job search hack on Reddit
I was reading comments on Reddit from people complaining about their job-hunting struggles, and I heard that some people had success by approaching hiring managers directly.
Some people said they were called cold, which made me think, “Well, that’s a little far,” but the emphasis was just to reach. The idea of emailing them seemed low risk, so I decided to give it a shot.
I started by researching LinkedIn, trying to guess who the hiring manager or recruiter might be. Sometimes it was listed, but it was not the best way. Then I came across a Reddit comment about Apollo AI, a free tool that can detect hiring manager emails. I found this to be perfect, so I started reaching out with my resume and cover letter. It was a game changer.
Sweetgreen’s CEO responded to my email
My messages showed initiative and, honestly, probably made things easier for the hiring manager. I approached three directly and interviewed for two jobs.
I also emailed Sweetgreen’s CEO directly, and he responded by putting me in touch with the hiring manager to schedule an interview.
One of my email outreaches turned into my current job, a strategy lead role for a major retailer. This strategy made things more efficient because I already had a direct line of contact, so it was easy to follow up if there was a delay.
I have had no negative feedback about it and would do it again
I was wondering if someone might be weird about finding my emails, but no one said anything. They could find it terrifying, but they could also find it resourceful.
If I were to go back to the job market, I would start with an email strategy. The exercise of thinking through creative approaches like portfolios and video cover letters was fun and made me think about how to present my personality most effectively, but ultimately, direct contact was the best way to be competitive.
Do you have a story to share about a unique job hunting hack? If so, please contact the reporter at tmartinelli@businessinsider.com.
Read the original article on Business Insider
