9 Creative Ways Top Performers Are Booking Meetings
(Part 2)
Read time: 3 min
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Last month, I served: 11 Creative Ways Top Performers Are Booking Meetings (Part 1). Missed it? Here’s the link to catch up.
Today, we’re plating part 2. And in December, part 3 will hit the table.
Not every idea lands a meeting, but outbound is tough, so why not spice it up? Most products are the same; creativity is the secret sauce to standing out and starting conversations.
Alright, let’s get cooking:
🚨 Chef’s Note:
These playbooks are creative, but they’re not Michelin-star magic. They won’t give you a 100% reply rate.
But if your reply rate was 0.5% and jumps to 5%, that’s a 1000% improvement. That’s what I call cooking with fire!9 Creative Ways Top Performers Are Booking Meetings (Part 2)
Recipe 1: 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.
Recipe 2: 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:
Recipe 3: 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.
BTL (Below the Line): We sent hot sauce. People loved it and even posted pics on LinkedIn—super easy to scale.
ATL (Above the Line): Gifts were personal: Champagne, whiskey, tequila, or something tailored, like a favorite sports team or a book they’d enjoy.
Recipe 4: 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.
Recipe 5: 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.
Recipe 6: Scraping for Thought Leadership with AI Using Clay
Shared by Lydia Winn, Sales and GTM at Empowerly
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+).
Optimizing Prompts: Be specific: Max 3 results, URLs only. Keep tweaking prompts to improve accuracy.
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.
Recipe 7: 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.
Recipe 8: 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.
Recipe 9: 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.
That’s a wrap for today, hope you picked up a few fresh ideas for Q4.
Got a favorite creative recipe you’re cooking up?
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I loved this one!! Cool initiative and good examples! :)