14.ai Dispatch #10
From Playbooks to Poker Faces
This week: a bestselling book, questionable poker bluffs, and a workshop from the Bellagio.
📚 Hot off the press (literally)
The AI-First Customer Support Playbook is here.
It’s your practical guide to designing, deploying, and evolving AI agents in modern support workflows, straight from the team that’s been building it in the wild.
Already ranked:
#1 Bestseller in Slack Channels
#1 in “Books That Trigger Zendesk”
Top 10 in “Books That Should’ve Been a Tweet”
Perfect for:
Your Zoom background shelf
Your support strategy
Your next dramatic airport read
📩 Email us for a free copy.
Prompt Battle Royale
Everyone’s a prompt expert… until it’s live.
We pitted support experts against each other in a head-to-head prompting showdown. Think less “Jeopardy!” and more “convince the AI to give up the secret password without breaking the rules.”
Bragging rights were claimed, questionable strategies were deployed, and at least one person is now banned from saying “statistically…” mid-prompt.
Check out our recap post here.
Founders & Engineers Poker Night Recap
Bluffs were made. Stats were cited. Chips were lost. Egos: mostly intact.
Big thanks to everyone who joined our quarterly poker night, where 80% of the game was bluffing and the other 20% was engineers justifying their losses with probability.
Same time next quarter? ♣️🃏
🎰 Workshop, Las Vegas edition: Growing your support org
What happens in Vegas usually lacks documentation...
Not this time.
We’re hosting our next workshop live from the Bellagio suite in Las Vegas.
Join us live for a tactical session with the incredible Jen Burton on scaling support the right way, without burning out your team or setting your inbox on fire.
We’ll cover:
When to hire (and who)
What metrics actually matter
How to build systems that won’t break at Series C
📆 August 12 @ 12 PM PT
How Secure is the Great Wall?
In the age of AI, can a stone wall really hold up?
In Case You Missed It:
Pinkie’s farewell feast - our private chef intern wrapped her final week.
Marie’s birthday - celebrated with an amazing cake.
Marie’s bedtime hack - costs money, but works.
Michael’s 5,000-line Monday - and still enough energy to write about it.
Advanced AI Knowledge Base workshop - live from Bangalore with Pageloop’s CEO.
💼Cool jobs at 14.ai (and friends)
In the market for something new? Or just here for the salary benchmarking?
🛠️ Founding Engineer @ 14.ai (San Francisco)
💻Technical Support Engineer @ Junction (EDT/EST, US East Coast Only)
⚙️Senior Manager, Technical Support Engineering @ Datadog (San Francisco)
Need an intro? We got you.
📚What we’re reading & listening to this week:
Marie: The AI-First Customer Support Playbook: A Practical Guide to Designing, Deploying, and Evolving AI Agents in Modern Support Workflows, by Michael Fester, Marie Schneegans, Maya Czeneszew, and Ugo Balducci
Maya: Knowledge Distillation: How LLMs train each other, Julia Turc
Ugo: Magic Ink: Information software and the graphical interface, Bret Victor
🫡 That’s all for now
See you at the poker table, and maybe in your bookshelf too.
Until then: eat well, code fast, and keep your knowledge base out of 2022.
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