How I Tried To Land My Dream Job with Bill Simmons

land my dream job the ringer

If you saw a posting for your dream job what approach would you take to try and land it? This post is about the approach I took to try and land my dream job with Bill Simmons.

As someone who is a sports writer and creator one of the people whose work I admire is Bill Simmons. He’s done some amazing things in the world of sports and I aspire to create a sports media company like he built at Grantland and now with his new project at The Ringer.

I saw a job posting that The Ringer is looking for a social media director. Someone who can create sports content and convey the tone of The Ringer on social media. Perfect, I’ve been doing that for the last 5+ years with Bacon Sports and considering I’ve been following Bill Simmons work for the last 15+ years I’d have no problem getting the tone down.

As you can imagine, getting on the radar of someone like Bill Simmons isn’t easy. It’s not like I can just pick up the phone, call him and say what’s up. The job posting said to email a resume over to a generic email, which unfortunately gives me very little control of the situation.

Since I likely have only one shot at this I decided to put my creative hat on and skip the traditional cover letter and go with a video pitch instead.

Instead of spending 3 minutes talking solely about my accomplishments I wanted to speak directly to my thoughts on social media, my personality, and my creative ability. No doubt there will be an endless amount of qualified people for the role. My bet is that few others will create a video and even fewer of them will stand out like I attempt to.

Once that video was complete I made sure to put in my email that they should watch this video first. I attached my resume and off it went.

Because The Ringer is a new venture there is very little points of contact or people to be found anywhere. Now this is the point where most people would just sit back, pray, and hope for the best. Not me. If you really want something bad enough then you’ve got to go all out. I wanted to give myself numerous opportunities to get on the radar of whoever was making the decision about this position.

Through my cunning detective abilities I was able to track down a mailing address for the Bill Simmons Media Group. With this key piece of information I then put together a care package. Included in it was a brief hand written note that referenced the video and included a link to watch it (I created a dedicated page on Cress Media so the URL was all pretty.) I also included a 1991 Dominique Wilkins Fleer card, which I also used as an analogy in the note.

dominique wilkins card

I also included a #FlagItTagIt penalty flag as it’s a unique, memorable, and fun item that is brand relevant, plus I can guarantee no one else is sending one of those. Lastly, I included one of my Bacon Sports business cards, which are flawlessly designed and stand out as much as any business card I’ve ever seen, as a way of contacting me.

I then went to UPS, put all of this in a mailer, which should hopefully stand out more than just regular mail, and sent it off.

Total cost: $7.
Total time spent: a couple hours.

Regardless of if I hear anything back this was a great opportunity for me to work on my creative hustle and pitch. I’m someone who believes in putting my work and myself out there and going big or going home. Like Eminem said in Lose Yourself:

If you had
One shot
Or one opportunity
To seize everything you ever wanted
In one moment
Would you capture it
Or just let it slip?


Are you looking for a sports creator with a 5-tool skill set (writing, podcasting, video, social media, production) to help grow and engage your audience? If so let’s talk ASAP about how I can be an asset to your team. Contact Rob Cressy at rob@cressmedia.com or via this webform.

Tags: ,

creativity  //  sports  //  Writing


Copyright © 2017 Cress Media Group LLC

Sports Content Studio

Cress Media is a Chicago Sports Marketing Content Studio. We help brands activate sports fans by telling their story in a fun and engaging way via audio, video, and social content creation. We get your audience talking, taking action, and having fun with your brand online and offline. Whether in Chicago or any other part of the country Cress Media can handle your content creation and sports marketing needs.