Actionable tips, community conversations, and marketing inspiration.

Scary Stories to Tell on Zoom 3: The Haunting of Ray Van Winkle

Angie Tran

Content Marketing Manager @ AdRoll

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It's almost Halloween, which means it's time for scary stories! No, not about demons, killer clowns, or creepy-crawlers, but about marketing failures. đŸ˜± This story of Ray Van Winkle, in particular, will send chills up your spine


Share these with your team members and peers for a light-hearted scare; with dead-serious advice to avoid becoming the main character in your own marketing horror story. 

The Sales Call From Hell đŸ”„

A cold call from a sales rep lures an advertising manager, Ray Van Winkle, to the sweet nectar of completely hands-off ads and emails. “Set up a few auto-triggers and nurture drips, and call it a day!” the software’s landing page promises.

“Just turn it on and forget it — no need for audiences, customer journeys, analytics, or adjustments.” Hooked by the compelling messaging and visually appealing interface, he quickly sets up a few mass email blasts and display ads. 

As he pushes more and more of his budget into the “set it and forget it” system, he finds himself putting off optimizations, revisions, and reporting. He was getting sleepier and sleepier. One day, he falls into a deep slumber, with the software slogging away in the background.

When Ray Van Winkle finally wakes up, he is shocked to find his office in shambles. A crumpled piece of newspaper billowing in the wind informs him that more than a year has passed. 

The company he works for no longer exists. No one remembers who he is. 

He scrambles to find answers by scrolling through hundreds upon hundreds of unopened Slack messages. Finally, he finds it — a statement from the CEO. Apparently, the advertising manager’s “set it and forget it” approach resulted in no actual growth. Instead, he had completely wasted the entire fiscal year’s marketing budget, and the company soon went under. 

Moral of the Story

It’s easy for marketers to become enchanted by the captivating promises of software that “does it all for you”. Whether it’s because your marketing team doesn’t have the experience yet or because you’re pouncing on all the newly available features at once, software can hurt you in the long run if you don’t have a plan to leverage it strategically. 


Though marketing technology (martech) can help execute your strategies more effectively and efficiently, mastering it requires developing expertise, analytical skills, and creativity. Remember: Martech won’t magically solve all your problems, and good marketing will never, ever be completely hands-off. 

Avoid the Burn of Bad Practices With These Tips

Choose the right software

Many advanced marketing tools are available for cheap (we’re talking less than $50 a month) — you just need to spend the time to figure out if they are appropriate for your brand and your growth goals. It’s also worth requesting a demo from sales reps so you can better compare different platforms. If you find that a particular tool provides adequate value to your team, don’t hesitate to upgrade to paid business or enterprise versions that better sustain scalability. 

Ultimately, you want to choose a vendor that’s committed to helping your brand succeed. Looking for the right match for your brand? Learn more about how AdRoll can help you save time and money.

Solve problems one by one

Marketers can become overwhelmed by the buzzy functions that their new automation software offers. A solution: Consider creating and prioritizing a list of sales and marketing pain points to guide your adoption of the platform. Rather than immediately experimenting with all the functions at once, use it to target individual marketing challenges one by one. 

Not sure how to expand beyond your current customer base? Use your software to create lookalike targeting. Want to find out how your latest campaign contributed to your overall business goals? Churn out some customer journey insight charts and maps in minutes. In other words: Don’t try to take on the whole platform at once. Instead, let your priorities steer your steps one at a time. 

Develop valuable content

Informative, entertaining, and compelling content is the driving force behind most marketing automation. Consistently producing quality content — especially content that supports multiple sales funnels, spans several platforms, and targets different audiences — requires a well-oiled process. 

Here’s an excellent overview of how to kick-start your content marketing efforts, beginning with creating a killer strategy. 

Don’t Be Haunted by the Ghost of Under-preparation

Start building your holiday marketing campaigns today! Find out how to strategize, create, and report in our resources below. Ready for another thrilling story? Click here to read number four.

Click on the image to download the background to use on Zoom or other video calls!

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