Onboarding Substack: Scaling a Tiny POC

Jacqueline Cheong is the Co-founder and CEO of Artie.

Artie moves data across your systems in real-time, and we talk about why that’s so important in the age of AI.

It’s a lot harder than you’d think, as less than 5% of real-time data streaming projects are successful.

I talked to a dozen people to prepare for this conversation, including Jared Friedman who worked with Jacqueline during YC, her sales coach Ras, and numerous Artie employees like A-nee-rud, Ryan, Sarah, Shangbing and Jacqueline’s co-founder Robin.

We talk through how Robin built real-time data streaming at OpenDoor and Zendesk before they started Artie, and Jacqueline shares the sales playbook she learned going from hedge fund analyst to software CEO, including asking customers for their hardest problem and then solving it with the product.

Artie just announced a $12 million Series A a few weeks before we published this episode. We talk about how they landed all of their early enterprise customers through cold outbound, how they structure and automate their prospecting with AI so they have no BDRs, and why they’re seeing customers switch to Artie even after building their own multi-million dollar real-time streaming projects in-house.

I also asked Jacqueline what it’s like working with Standard Capital. They’re a new fund started by a group of YC partners, and it was fascinating to hear about the things they’ve borrowed from YC when investing at the Series A stage.

Try Numeral, the end-to-end platform for sales tax and compliance: ⁠https://www.numeral.com⁠

Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz

Timestamps:

(4:08) Artie: Real-time data streaming

(5:13) Why moving data is so hard

(9:14) Evolution of data warehouses

(12:47) AI needs real-time data

(18:44) Build vs buy in data streaming

(22:51) How to build in a crowded market

(26:26) Early focus on a specific hard problem

(30:33) Acquiring enterprise customers from cold emails

(32:51) Onboarding their first customer with no UI

(35:46) Solving compliance and implementation

(38:50) How to automate internal engineering, marketing, and ops

(44:01) Building an AI-powered GTM pipeline and motion

(46:52) Add your customers on iMessage, Slack, Teams

(53:00) Starting Artie to solve their own problem

(59:25) Discovering YC through a friend

(1:02:20) Everything Jacqueline learned about sales

(1:06:29) How to improve your sales discovery calls

(1:10:08) Inside Artie’s $12m Series A

(1:16:44) What its like working with Standard Capital

(1:22:59) Jacqueline’s favorite book

Referenced

Try Artie: https://artie.com

Careers at Artie: https://www.artie.com/careers

Clay: https://www.clay.com

Podcast with Tommy @ Alloy: https://www.youtube.com/watch?v=e7i8Wxklu-Y

YCombinator: https://www.ycombinator.com

Standard Capital: https://www.standardcap.com

Founding Sales: https://www.foundingsales.com

The Score Takes Care of Itself: https://www.amazon.com/Score-Takes-Care-Itself-Philosophy/dp/1591843472

Follow Jacqueline

Twitter: https://x.com/JacquelineSYC19

LinkedIn: https://www.linkedin.com/in/jacqueline-cheong

Follow Turner

Twitter: https://twitter.com/TurnerNovak

LinkedIn: https://www.linkedin.com/in/turnernovak

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