"The dream is to be the system of record for customer support that really helps you identify how to make it really good."

This week on Skywatch, Bluejay's car podcast, I sat down with John Wang, co-founder and CEO of Assembled, and we had a conversation about what it actually looks like when AI agents meet enterprise customer support at scale, and what most people are still getting wrong.

John did not start out building customer support software. After an MIT roommate steered him toward coding over economics, he finished school early for YC and joined Stripe. There, he and his brother developed an internal system saving millions, only for a PM to prioritize a Bitcoin project instead. That pivot point is what built Assembled.

A few highlights from this conversation I have not stopped thinking about:

👉 Although a fully automated experience is ideal, any lapse in service causes customer satisfaction to fall off a cliff, highlighting that knowing exactly when to involve a human is the greatest challenge in customer support AI right now.

👉 While a top-tier human agent might still outperform AI today, the technology excels by delivering what John calls the Chick-fil-A effect, a level of absolute consistency that ensures every customer knows exactly what to expect, every single time.

👉 John's analysis of his customer base revealed that 75 to 80 percent of companies implementing AI agents increased their headcount, due to automation driving higher volume, creating more complex support tickets, and requiring long-term change management.

If you are building in customer support, voice, or enterprise AI, this one is worth your time.

Full episode on YouTube and Spotify 👇

Spotify: https://open.spotify.com/episode/0tZjnohLe9IooI8iStr2l4?si=OpMQGiZhQ5KfWQJN9g5C_Q

Youtube: