John O’Toole

Advertising Copywriter |Creative Human!| 😎✌🏼🕺

Let’s chat 💬 630-254-6566 | johnotoole930@gmail.com  

Behold, the riveting tale of my work life so far, conveniently condensed into this thrilling document. You're in for a wild ride – it's my resume :)

Experience 

Book 180, 2026 – Present

Instructor

Teaching the craft of copywriting to future advertising copywriters—one headline, deck, and “wait, can we make it shorter?” at a time.

Word.

Freelance Copywriting, 2023 – Present

Senior Copywriter / Creative Direction 

  • I’m your word maestro, ready to craft ideas for any cool project that comes my way. Here’s a glimpse of some recent fun:

    Los York/ Doing videos and other cool stuff for Lenovo.

    Anaheim Studios / Wrote and concepted social video scripts for Vicks Painquil and Old Spice, plus developed new campaign ides for new business.

    Dentsu / Writing social and digital content on the rad Adobe team.

Invisalign / Conceived, penned, and executed a vibrant spec campaign that truly dazzled—so much so that I personally presented it to the client.

Quigley-Simpson / Brought the Instacart Mastercard to the bright lights of Times Square with a dazzling billboard and dreamed up Gen-Z savvy concepts for the Marriott Bold Card.

/ Co-created, crafted, and sold a nationwide TV spot for Southwest Airlines’ Rapid Rewards Plus Credit Card—because earning points is the ‘Biggest Flex’ of them all.

EarnIn / Spiced up the social scene for the payday app everyone’s talking about.

J. Schmid / Crafted engaging LinkedIn posts for Kansas City's dynamic business consultancy, Entrepreneur to Enterprise (e2E).

Dentsu Creative, 2025 – 2026

Associate Creative Director / Copywriter

  • Making pixel-perfect mischief on Adobe by:

    Concepting, writing, and producing the social ‘Mascot Playoffs’ campaign—where our team, creators, and MVP runner-up Cal “The Big Dumper” Raleigh (who I got to interview Bob Costas style) cooked up their own mascots using Adobe Firefly. Thousands of fans jumped in to vote, engagement around Firefly skyrocketed, and one very goofy bull strutted away with the crown. Safe to say… this campaign was a total home run.

    Creative directing and assisting strategy by developing creator personas for paid social (gearheads, outdoor chefs) that we could speak to directly. Instead of generic marketing copy, we used fun, conversational language that actually resonated. The results? Tons of impressions, and Adobe adopted this persona-driven approach as part of their ongoing strategy.

Sidecar Health, 2021 – 2022

Senior Copywriter 

  • Played a crucial role in shaping the vibe and voice for a startup in the health insurance game.

  • Revamped Sidecar's website with conversational language, developed member welcome kits.

  • Created, crafted, and launched a digital campaign catering to freelancers.

Quigley-Simpson, 2016 – 2021

Senior Copywriter

  • I whipped up words, took the lead, and cooked up all-encompassing campaigns for pretty much every Chase credit card, plus Starbucks, Budget, Lyft, Paycom, and even BeWaterWise.com.

  • Brought in and looked after the newbies in the copywriting crew.

 

FCB Chicago, 2013 – 2016 

Copywriter 

  • Crafted words and cooked up full-blown campaigns in every direction for Cox Communications, Michelob Ultra, Kentucky Fried Chicken, T-Mobile, and Valspar. 

RPM Advertising, 2013 

Junior Copywriter 

  • Learned the ropes on clients that included BMW and Hollywood Casinos. 

Frequency Television, 2008 – 2009 

Writer/Producer 

  • Wrote, produced, and created programming for the station (including a show called Get Tipsy that was not about drinking).


EDUCATION

Chicago Portfolio School, 2012 – 2013 

Copywriting 

Columbia College Chicago, 2006 – 2009 

Bachelor of Arts in Television – Writing/Producing 

ETC. 

  • Former looper (I still quote Caddyshack all the time). “I enjoy skinny-skiing, going to bullfights on acid…”

  • Got this silly running blog on Instagram. It's kind of a big deal (not really). Follow @JohnRunsHard for some not-so-athletic adventures.

  • Proficient in multitasking: Managed two daughters, countless eye rolls, and maintained dad-joke supremacy with exceptional flair. 

  • I love mentoring advertising students from my alma mater. Consider me the Gandalf of ad advice –“You shall not pass without a killer campaign idea!”