11 Creative Ways Top Performers Are Booking Meetings
(Part 1)
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Tired of sending emails? Want to make Q4 your best quarter ever? Or looking to help your team finish the year strong?
I’ve put together a collection of 11 creative (and sometimes funny) ways that top reps are booking demos.
Not all of them resulted in meetings, but outbound is tough—so why not add a little fun?
Remember, most products are similar, so getting creative is often the key to standing out and sparking that first conversation.
Alright, let’s dive in:
P.S. I’ve got over 25 creative ways to share, so this could easily turn into a 3-part series! (Or more—who knows!)
11 creative ways that top reps are using to book demos
#1 - 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!
#2: 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!
#3: Puppy + Whiteboard
I reached out to Amanda Wilde, Director of Business development, o 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!
#4 - 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.
#5 - 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!
#6 - Office drop + Whiteboard
This one comes from , 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.
(Unfortunately, no example online, but you get the idea!)
#7 - 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!
#8: 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!”
#9: 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!
#10: 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.
#11: 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?”
You can’t send a toy to every prospect, but it’s a brilliant way to stand out.
Relevant: Tied directly to the prospect’s role as a “digital transformer.”
Creative: Using a playful metaphor like Optimus Prime to connect with the message.
Tangible: Physical gifts leave a lasting impression that digital touches often don’t. When it’s fun and aligned with the messaging, it’s even more memorable.
What’s the most “creative” outreach move you’ve pulled off lately?
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So cool ! I laughed !