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The Long Game with guest Joanna Toronto

The Holiday Ad Playbook: How to Win When Costs Go Up & Attention Goes Down

Insights from The Long Game with Jessika Suter, Jeremy Knauff & Joanna Toronto

The holidays are here… and so is the chaos.

Budgets go up. Attention spans go down.
 And every brand is scrambling to squeeze into the same noisy window of the year, hoping one more ad will magically cut through and convert.

But if you’ve ever felt like your holiday ad strategy is… well, a little “Island of Misfit Toys,” you’re not alone.

In this week’s episode of The Long Game, Jeremy Knauff and I sat down with NOW Marketing Group’s Ads Manager Joanna Toronto.. Aka the woman behind the data, the dashboards, and the wins for a real conversation about what actually works for brands heading into the holidays.

And Joanna did not hold back.

Here’s the full playbook she shared so you can compete smarter, not louder, during the busiest marketing season of the year.

Why Holiday Ads Fail: The #1 Mistake Joanna Sees

Let’s start here, because it’s real:

Last-minute ads = last-minute results.

Joanna sees it every year:
 Brands show up on Thanksgiving night ready to “throw something together” because Black Friday is coming.

When planning is rushed:

  • Your message doesn’t match the moment
  • You don’t stand out from competitors
  • Creative feels irrelevant or flat
  • You miss your best window entirely

But the biggest issue?

You’re not speaking to the actual mindset your customers are in.

Holiday shoppers fall into three buckets:

  1. Early planners (think: Jeremy—done by October)
  2. Regular-paced shoppers
  3. Last-minute chaos buyers (think: Joanna—buying on Dec. 21st)

Each of these groups needs completely different messaging.

And that brings us to…

The Big Switch: Holiday Ads Require a Different Strategy

The ads that perform well the rest of the year don’t always work during the holiday season.

Why?

Because buyers shift from:

  • “I’m exploring options…”
     to
  • “What’s the deal? How fast can I get it? Will it arrive on time?”

That means your ads must shift too.

Joanna’s must-use holiday messaging themes include:

  • Limited-time sales
  • Can’t-miss deals
  • Shipping guarantees (next-day, 2-day, etc.)
  • Fast fulfillment
  • Last-minute convenience
  • Giftability (“this makes the perfect…”)

Holiday shoppers buy with urgency, not curiosity.

Should You Even Run Holiday Ads?

Hot take from Joanna:

Not every brand should advertise during the holidays.

Yep. She said it.

If your product isn’t a natural holiday fit or if your budget is tight you may be better off investing in:

  • Organic content
  • Email marketing
  • Community engagement
  • Planning for your real peak season

Why compete with Walmart, Target, and Amazon when your customer isn’t even in buying mode right now?

Joanna reminds brands:

“You don’t need to advertise everything. And you definitely don’t need to buy everything.”

Can we get an “Amen”

The Secret Weapon: Creative Diversity

Holiday ads that win share one trait:

They test and use a lot of creative.

Especially with Meta’s new structure, platforms reward brands who upload multiple versions of:

  • Static images
  • Short videos
  • UGC clips
  • Testimonials
  • Carousel formats
  • Offer-based graphics

The platform will decide what version resonates best with each buyer type.

Your job?
 Give it options.

Using AI the Right Way in Your Ad Strategy

AI is everywhere… but so are the wrong ways to use it.

Joanna called it out:

“People are starting to spot the copycats. Low-effort AI ads kill trust.”

Instead of copying competitors or pasting screenshots into ChatGPT, Joanna recommends using AI to:

  • Analyze buyer personas
  • Compare product alternatives
  • Identify messaging gaps
  • Generate fresh angles from proven creative
  • Refresh existing content without reinventing the wheel

AI should amplify your humanity (not replace it)

Where Should You Run Ads? (Meta vs. TikTok vs. Google)

There’s no one-size-fits-all platform.

Here’s Joanna’s take:

TikTok Shop

Great for impulse buys, UGC-driven items, and fast-viral products.
 But also the Wild West ie where knockoffs, aggressive ad loops, and “dropshipping clones” are common.

Meta (Facebook + Instagram)

Still king for:

  • Targeting
  • Creative testing
  • Retargeting
  • Personalization
  • High-intent traffic

It rewards brands who upload LOTS of quality creative, not just one or two versions.

Google & YouTube

Great for:

  • High-intent searches
  • Product categories people research
  • Evergreen buying seasons

Your brand may need a mix, depending on product type, price point, and audience behavior.

Stop Wasting Ad Spend: The Retargeting Mistake Everyone Makes

You know when you buy something online, and the brand STILL advertises that exact product to you?

That’s because someone didn’t exclude recent purchasers.

Joanna recommends:

  • Excluding buyers in your pixel for 30–180 days
  • Removing them from retargeting audiences
  • Serving them new-product or add-on ads instead

Marketing to someone who JUST bought from you burns the budget and annoys customers.

The Most Important Metric This Holiday Season

Hint: It’s not ROAS.

The most important metric is new customer acquisition.

Especially for:

  • Apparel
  • Beauty
  • Consumables
  • Subscription products
  • Home goods

Many brands don’t profit immediately during the holiday season…but they acquire customers who return in January, February, March…

You’re playing the long game.
 (Not the “quick cash grab” game.)

Joanna’s Top Questions Every Brand Should Ask Before Running Holiday Ads

If you’re launching ads now (yes, even mid-November), ask: 

  • Is my product a natural holiday fit?
  • Do I have strong creative ready to go?
  • Do I understand early vs late shopper behavior?
  • Am I prepared for higher ad costs?
  • Is new customer acquisition more important than immediate profit?
  • Do I know which platform fits my audience?

If the answer is no to most of these…
 Your ad dollars are probably better spent elsewhere.

What To Do If You’re Late to the Game

If you’re reading this on November 18th and panicking?

Breathe.

Here’s Joanna’s advice:

1. Don’t overcomplicate it.

Use the best-performing creative you already have.

2. Don’t advertise everything.

Focus on 1–3 products max.

3. Review this year’s analytics.

That data sets up your 2026 success.

4. Prioritize trust first, ads second.

Strong relationships lower future ad costs.

5. Use what you learn now for next year’s plan.

Holiday 2026 planning starts… well, basically now.

The Long Game Takeaway(s)

Holiday ads aren’t about shouting louder.
 They’re about showing up smarter.

When you understand:

  • buyer behavior
  • emotional timing
  • platform rules
  • creative diversity
  • and trust-driven messaging

… We will stop wasting money on ads that disappear into the noise.

We will start attracting the right customers ie. the ones who buy from you again, refer you often, and become true fans.

That’s The Long Game.

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