I interviewed Ryan Wang, co-founder and CEO of Assembled, in his San Francisco office to unpack how he turned lessons from Stripe into a fast-growing startup that powers customer support teams at Robinhood, Canva, and Notion.

We talk about:

• Finding the right co-founders and surviving a CEO hand-off
  
• Discovering product-market fit by asking one powerful question
  
• Turning a “sleepy” support category into a $200 billion opportunity
  
• Launching a second product with a startup-within-a-startup mindset
  
• What it takes to lead through AI disruption and build for adaptability

Whether you’re building your first team or figuring out your second act, Ryan’s story is a masterclass in scaling deliberately while staying flexible.

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(2:35) “ I was employee number 80 or so at Stripe working on machine learning for fraud detection.”

(5:08) If you’re doing diligent customer discovery, working harder does not get you ahead faster.

(7:27) How Assembled’s founding team, er, assembled.

(8:47) “ There was a period, maybe the first year and a half or so, where there was no CEO.”

(10:33) Ryan explains the mindset that took him from software engineer to CEO.

(12:30) “ ‘Brother mode’ is both a feature and a bug at the same time.”

(14:58) How Assembled arrived at workforce management as its unique value proposition.

(17:48) Ryan talked to more than 100 prospects during the customer discovery process.

(19:00) The exercise they used to develop their initial customer personas.

(22:24) “ We took a really, really long time to hire for product. It was probably four or five years into the company.”

(25:00) Who was Assembled’s first design hire?

(27:26) To acquire product-market fit, “ we started with just a simple automation value proposition.”

(30:26) “ A lot of folks wanted to invest in Stripe alums, and Stripe led our seed.”

(33:35) Why customer support ops is — and will continue to be — such a huge opportunity.

(36:41) A good mission statement defines the change you want to see in the world.

(41:41) “ People who really do feel committed to a large mission, they understand that to get there is gonna require a lot of schlep.”

(43:55) How Assembled used a startup-within-a-startup mindset to innovate.

(48:47) “ We reassigned folks internally, and the key really was the order of operations.”

(51:31) If you were interviewing for a job with an early-stage startup, what’s one question the CEO would have to answer before you could take the offer?

Assembled

Ryan Wang

Brian Sze

John Wang

Stripe

Kelly Sims, Thrive Capital

Jack Altman, Alt Capital

Jen Ong Vaughan, Head of Strategic Ops, Stripe

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Thanks for listening!

– Walter.