Career Crashers Episode 16: Kevin Cherrick on Winning Job Opportunites

Morgan Von Gunten
May 2019

Success is not final, failure is not fatal: it is the will to continue that counts.

Winston Churchill

Kevin Cherrick was looking for a sales job. He applied to a role at a startup he liked, but two weeks later, he still hadn’t heard back.

So he did a lot of research, went to Costco, bought $150 worth of snacks, crashed the startup’s happy hour, and set up an interview with the hiring manager.

After the interview, he was rejected.

But he didn’t take no for an answer.

He found a way to show who he was in ways a resume could not.

And he turned a rejection into a job offer.

On this episode of Career Crashers, Kevin, an entrepreneur and currently a digital marketing executive at FreightWaves, shares his story and approach to the hiring process–and how he uses it to win great job opportunities.


  • The process Kevin went through to identify and pursue job opportunities
  • How to research the company and industry you’re targeting to find out if you’re interested
  • Why and how you should reach out to front-line employees at your target company to learn more about it
  • Kevin’s story of joining a company happy hour as a way to get a leg up in the hiring process
  • Using rejection for one position as a doorway to other opportunities at the same company or others


Connect with Kevin on LinkedIn: linkedin.com/in/kevincherrick

Read Kevin’s detailed breakdown of his job search on Medium here.


Also listen to this on iTunesSpotifyAnchorTuneIn, and Overcast.

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You can stay up-to-date on every Career Crasher episode as it launches here. Plus, if you’ve got a story or know someone who we should feature, don’t forget to email us!

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