🎁 37 Creative Ways Top Performers Are Booking Meetings

(Perfect to prep 2025)

Read time: 11 min

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Last newsletter of 2024! 🥳

Time to recharge, plan for 2025, and come back stronger.

To prep your new year, I’ve put together 37 creative outbound ways, fun ones, serious ones, and everything in between. Perfect for testing and making outbound work in 2025.

See you next year, and let’s crush it!

Here’s the big list👇

37 Creative Ways Top Performers Are Booking Meetings

1: Using their prospects’ tools

By Alex Jagiello, Director, Commercial Sales at Descope

Some of the most creative ways SDRs book meetings are when they target SaaS companies and actually use the company’s own tech in their outreach.

For example, his team went after Notion. Instead of just sending a boring email, they built a Notion page that hit home with the prospect.

2: Taco Costume + Email Image

By Will Falkenborg, SDR lead at Champify.

Here’s a bump email that actually worked (but there’s a catch): it works best on Tuesdays.

Will had a referral to a prospect he admired at a great company from an SVP. Sent 4-5 touches, nothing. Then, 10 days later, his taco suit arrived in the mail, and he went for it:

Why it worked:

• Read the room and went with humor

• Made the ask approachable, not pushy

• Who can ignore a taco on a Tuesday?

3: Enterprise Reports

Mark Roberge (Ex-CRO at HubSpot) once said on a podcast how the best Enterprise AEs crush it:

They don’t just wing it. They spend two months researching public companies. They buy the product, try it out, and build super-detailed reports.

Then, they send those reports to marketing execs.

4: Image on Linkedin

By Will Falkenborg, SDR lead at Champify.

How he 4X’d my LinkedIn response rates:

Here’s the simple framework:

1. Send a LinkedIn voice note.

2. Follow it with a photo of a handwritten whiteboard.

3. Bump the message with, “Was my handwriting that bad?”

5: The Cameo Play

When Sarah Brazier (ex-Gong AE) couldn’t get through to an enterprise prospect, she pulled a wild move: hired a celeb from Cameo to record a personalized video, and closed the deal.

Here’s how it went down:

• Sarah wanted NFL player/Old Spice icon Isaiah Mustafa to spoof his famous line: “The rep your rep could sell like.”

• Rules said no. But she found out Mustafa used to work in sales.

• Pivot: She got Mustafa to make a personalized Cameo video for her prospect at Plixer.

The setup:

• Sarah added the video to Drift Video so she could track views.

• Then, she sent an email explaining why a meeting would help Plixer.

6: Music + Email

Dan Solomon shared this with me:

“I’ve got to give credit to my rep, Jace Davis. He’s brilliant at weaving songs or artists a prospect mentions on LinkedIn into his first email. It’s not some groundbreaking tactic, but his constant creativity makes it work.”

7: Last name

Dan Solomon shared another one with me:

Shoutout to Kyle Bell, one of my old reps. He looked up everyone in our ICP with the last name “Bell” and sent them emails like, “I doubt we’re related, but I’d love to help a fellow Bell.”

It worked like magic.

8: Office Drops

Andy Laws shared this gem with me:

If you’re in town, tell them. Drop off some swag or goodies at their office and try to meet them. If they’re not there, take a selfie outside their office with the gift. Then email them with the pic!

9: Spotify Playlist

At Chili Piper, we got creative with follow-ups using Spotify playlists. We’d create a playlist for the prospect, send a screenshot, and add a message like, “I made this Spotify playlist for you.”

10: “Blind calendar invites”

Anastasia Chihai shared this move:

Send blind calendar invites to referrals you got from other prospects. Follow it up with a LinkedIn voice message. She said it has a 30% acceptance rate.

11: Ketchup costume + Whiteboard

Jacob McLeod shared this one with me: He dressed up in a ketchup bottle costume and held up a whiteboard that said, “Just ketch-ing up with you.”

12: Gift: Hourglass

When JC Pollard (Gong) was an SDR, he cold-called a VP of Sales. He liked the pitch, was interested, but hit him with “not the right time.” He couldn’t overcome the objection on the call. So, he sent him an hourglass as a gift with this message:

“Hey [Name], I know timing is everything. But I’m confident once you see Gong, your mind will change. Open to a call? It won’t take longer than the flip of this hourglass.”

Result? Meeting booked.

13: Invite to Forrester

Austin Jouett cold-called a prospect and ended up chatting for 34 minutes. He found out she wasn’t planning to attend Forrester that year.

What did he do? He got approval from the exec team, booked her a flight and hotel, had dinner with her, and a few months later closed one of the biggest deals in the company’s history.

14: Gift: Hourglass

JC Pollard (Gong) was working with a champion who believed the best sales reps are “invisible”, they make the whole buying experience about the buyer, not themselves.

The prospect also mentioned his kids just went back to school.

So, JC sent him a pack of invisible markers with this note:

“Hey [Name], excited to show you how Gong can help turn your sales team ‘invisible.’ Hope your kids have some fun with these as they head back to school!”

15: The Rebel Letter Campaign

Dale Dupree, founder of The Sales Rebellion, knows how to grab attention. His “Rebel Letter Campaign” flips the script on boring prospecting.

Here’s how it works:

• Crumpled Letters: Deliberately messy, stamped, and “world-traveled” to stand out from the junk mail pile.

• Self-aware Message: One example: “Wondering why this is crumpled? 90% of sales and marketing is trash. I pre-crumpled it for you to throw away faster.”

16: Video + Dancing

This one was made by Will Falkenborg, SDR leader at Champify.

This prospecting video didn’t get Will a reply, but here’s what happened:

Their prospect was a Zumba instructor, so what did they get out of it? A workout, and some fun.

People often think “creative outreach” isn’t worth it just because a few don’t reply. That’s like saying you’ll stop cold calling because most people don’t pick up!

The goal? To have fun, make quality outreach, and amplify a well-crafted message that grabs attention and helps you stand out.​

I’m loving Will’s creativity on this one. It’s something you just can’t send to anyone—it’s personalized, unique, and stands out!

17: Voice Notes + Image + Whiteboard

Here’s another creative way from Will. He’s all about sending a voice note with a picture of himself pointing up at the voice note in LinkedIn DMs.

But here’s the twist: it works best on Tuesdays.

Want to take it up a notch? Add your prospect’s name on a whiteboard in the pic. It’s personal, and you can’t scale that kind of touch!

18: Puppy + Whiteboard

I reached out to Amanda Wilde, Director of Business development, to ask about a creative outreach, and she shared this gem: One of her BDRs, Roxy Radaczynska uses a picture of her adorable puppy with the line, “Barking up the wrong tree?”

Just like Will’s follow-up, this one works for everyone.

I was thinking about taking it up a notch like Will’s Taco follow-up, but as a dog owner, I know getting a new pic for each prospect would be a challenge. Haha!

19: Another: Puppy + Whiteboard

20: Email + Picture + Messaging

This one comes from Celine Hoyle, top performing BDR at Mosaic.

She’s been trying something recently that’s gotten a few laughs from her prospects. She snaps a picture of herself in front of a big screen with their logo on it and a clever message related to Mosaic.

The result? She booked the meeting.

What I love about this approach: It’s personalized for each company, and she even weaves their language/name into the email copy.

21: Another Email + Picture + Messaging

22: Office drops + Donuts + Picture

This one was shared on the podcast by Luis Buitrago, AE at Braze.

If a prospect opens your email 17 times but never replies, their move is to grab a box of donuts and show up at the office. That way, the prospect has no excuse not to chat over coffee or book a meeting on the spot!

23: Office drop + Whiteboard

This one comes from Pierre-Emmanuel Branger,Sales Leader.

He knows a rep in London who takes a bold approach—he goes right in front of his prospects’ offices with a whiteboard asking for a meeting, films it, and then sends them the video.

24: AI + Visual

This one was shared by Maureen Lavigne, Ex-BDR at Alan.

They’ve started adding AI-generated images of the company’s mascot, but in a fun, company-specific setting. For example, if they’re prospecting a food transport company, the mascot is shown driving a cute little truck filled with food. They throw in a playful line like, “I worked on an illustration of our mascot getting ready to dive into your world!” It’s a bit cheesy, but apparently, people used to do this at Alan, and it worked!

25: Picture + "Costco” drops

This one was shared by Jill Bruno, Co-Head of Sales Development at Altisales.

One of her reps works with software that helps boost social media influence for CPG brands. So when he’s out shopping at places like Costco or the grocery store, he snaps a pic of a fully stocked shelf of their products. Then, he sends the company a message like, “Work with us, and these will fly off the shelf!”

26: AI + Music

This one was shared by Max Kouris, Co-Head of Sales Development at Altisales.

Lately, his SDRs have been getting creative by making custom songs for certain personas using Suno.com (or something similar). You can choose the genre—rock, rap, country, whatever—and type in the prompt for what you want to say. And the crazy part? It actually works!

27: Gift: Nintendo 64

This one was shared by Austin Jouett, Full-Cycle AE.

So there was this prospect who absolutely LOVED video games—she was a paid media director at the time. She’d commented on a post about N64 games, so they sent her a full Nintendo 64 console with the game she mentioned, plus a GameStop gift card. No CTA, just the gift. She messaged back, super grateful, and wanted to learn more about what they did. A few months later, she ended up buying the software.

You can’t send a gaming console to every prospect, but it’s a genius way to stand out.

• Hyper-Personalization: Sending a Nintendo 64 with the exact game the prospect mentioned takes personalization to the next level—way beyond the usual cookie-cutter approach.

• No Pressure: There’s no hard sell here. Sending the gift without a pushy CTA makes the outreach feel more genuine and less salesy.

• Emotional Impact: Tapping into the prospect’s nostalgia and love for gaming hits them on a personal level, triggering positive vibes and making the outreach memorable.

28: Gift: toy: Optimus Prime

Found this one on LinkedIn, JC Pollard, AE team lead at Gong, is all about personalized gifts. In one month, he sent out 4 gifts to CEOs, and GTM leaders.

He got 4 replies:

• 1 “thank you, but now’s not a good time”

• 1 “thank you, but we’ve already got a competitor”

• And 2 meetings booked.

That’s a 100% reply rate and a 50% meeting booked rate!

One of the responses from a CEO at one of his top accounts came from sending a $24 Transformer toy with this note:

“As a digital transformer, I’m sure you’ve got a lot on your plate… but what if Gong could be the Optimus Prime of all your transformations? Worth a quick chat?”

29: Email AI + Springboard + Analogies

Here’s one from my kitchen: I saw on LinkedIn my prospect did springboard diving in college. Cool, but I know nothing about diving, and I’m not a native English speaker, so crafting analogies isn’t my strength.

Solution?

ChatGPT or Claude. They whipped up killer, relevant analogies tied to the companies I’m working with.

30: Poems

The first time I saw this was from Vilhelm Fridell (ex-Chili Piper). He sent poems as cold emails or LinkedIn messages. Genius.

This year, one of my BDRs, Quentin Naye, used it when he noticed a prospect was a big poetry fan. Sheriff Shahen told me he’s done it too.

With ChatGPT or Claude, it’s fast, simple, and makes your outreach stand out.

Here’s a ChatGPT-crafted poem for the Chief Data Officer of Nike:

31: Gifts: ATL vs. BTL

At Chili Piper, we used gifts across the funnel. For outbound, the focus was booking meetings and reducing no-shows

We never used boring Starbucks or Amazon gift cards to book meetings—everyone does that. We saved gift cards for one thing: reducing no-show rates.

We were sending gifts for both ATL and BTL.

1. BTL (Below the Line): We sent hot sauce. People loved it and even posted pics on LinkedIn—super easy to scale.

2. ATL (Above the Line): Gifts were personal: Champagne, whiskey, tequila, or something tailored, like a favorite sports team or a book they’d enjoy.

32: Gift: toy drones

Found this gem on Reddit.

A rep working for a drone-mapping company sent 10 $40 toy drones, gift-wrapped in custom company-branded paper. Each package included a note: “Want to see how real drones can help? Give me a call.”

Results: 4 meetings booked, 2 gifts were returned due to company policy, and 2 new clients closed.

Creative, bold, and it worked.

33: The Champagne Campaign

Shared by Sam Blond on SaaStr’s CRO Confidential. Brex ran an outbound play targeting 300 Bay Area startups that raised funding in the last 6 months.

Here’s the dish:

• Sent 300 bottles of Veuve Clicquot ($50 each) with handwritten notes saying, “Congrats on your recent fundraise! Building a startup is hard, and we’re rooting for you.”

• CEO followed up with an email offering a demo.

Results:

• 75% booked a demo (225 demos).

• 75% of those became customers (169 new clients).

• Total cost: ~$19k.

• If they’d done this today, they’d be getting ~$20M ARR. (Today’s ACV: $120k - Repvue 2024)

Why it worked:

• Personal touch: Handwritten notes felt thoughtful.

• Perfect timing: Targeting companies flush with cash.

• Memorable: Champagne beats boring cold emails.

• Solid product: High conversion shows Brex delivered value.

34: Scraping for Thought Leadership with AI Using Clay

Shared by Lydia Winn, Sales and GTM at Empowerly

1. The Process: Use LinkedIn profiles, work emails, and domains to enrich data in Clay. Find content via LinkedIn activity + Google searches (keywords: “articles,” “thought leadership,” etc.). Focus on recent stuff (2023+).

2. Optimizing Prompts: Be specific: Max 3 results, URLs only. Keep tweaking prompts to improve accuracy.

3. Results: 8/10 success rate so far, but refining prompts could nail harder-to-find profiles.

Takeaway: Clay + AI tools like ChatGPT make scaling personalized outreach easier by automating content discovery.

35: Lottery Ticket

Saw this on Bravado, a rep sent fake scratcher tickets to C-suite prospects. The “grand prize”? A Yeti with their company logo.

Each ticket was a winner, and to claim it, prospects had to reach out. Simple, clever, and it sparked great conversations.

36: Video Magic

Shared by Jenny-Hawa Semasaba, SDR Program Manager at Veed.io

One of her SDRs re-engaged a ghosted prospect (a retail trainer) with a custom video. The video demoed POS training, showing how much more engaging and interactive their product could make it.

The kicker? The SDR highlighted how quick and easy it was to create, a major selling point. The visual hook grabbed the prospect’s attention and sealed the deal.

37: The “FedEx Delivery” Trick

Heard this one on a podcast with Sam Blond, ex-CRO at Brex.

An SDR from Talkdesk showed up at Brex HQ, and claimed he was a FedEx guy with a package for Sam, just to get past security and talk to him.

Creative? Yes.

Risky? 100%.

P.S. It’s clever, but lying to prospects can backfire hard. I wouldn't do that. Use with caution.

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What's your favorite creative way from the list?

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