Lenny Distilled

Building a culture of excellence | David Singleton (CTO of Stripe)

May 04, 2023

Featuring: David Singleton (CTO, Stripe), David Placek (Founder, Lexicon Branding)

12 quotes · 8 insights

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Your calendar reveals your true priorities

On Sunday evenings, I actually write a list for myself of if we got these things done this week, that is a good week. I make a list and honestly, then, that drives a lot of just where I decide to spend my time.

Scale breaks everything - adapt your leadership style or fail

I personally will not be involved in really any of the decisions that matter and happen. There are thousands of decisions that an organization of any skill is making every single day. The most important thing is to really focus on hiring the right people, and that means hiring people that you can trust with a tremendous amount of autonomy.

Everything new starts as 10% of your time

Because we have operating principles of users first and being meticulous in our craft, we actually tend, all of our ways of building plans tend to be wired quite well around this idea that we're going to reserve enough time to really make the experience good.

Opinionated products beat flexible ones

You don't want to make a statement here. You want to start a story.
David PlacekFounder, Lexicon Branding 00:13:27
Your brand name, nothing's going to be used more often or for longer than that name. Design will change, messaging will change, products will change, but that name is there.
David PlacekFounder, Lexicon Branding 00:00:00

AI adoption starts with leadership doing the work

I'll clear several days in a road, three or four days actually join a team, pick up a small task, hopefully a small feature that we can get all the way from start to finish in production and do that going through the exact experience the team has. While one does that, it's really valuable and important to keep a friction log because then what you want to do is write up the experience.

Error handling deserves more code than the happy path

There's actually more code in the jobs that serve the Stripe API to handle those edge cases than in the actual main flow. And I think that's quite remarkable. Most people wouldn't do that, but it turns out not only was it something I was impressed with, but when I talk to Stripe users, this is very frequently something they tell me and delights them about the product.
We choose to design the way we work to hold those two things true at the same time. So we can operate very rapidly but also be extremely reliable and available for our users. It does take a lot of care and attention and it takes a lot of systems.

Build with customers, not for them

The way we think about product development at Stripe, it really is to find the correct set of early users to kind of co-create the product with. So we had shared Slack channels, we'd actually show them product on a very regular basis, get their feedback on it. And only when that original kind of Alpha group was super, super happy with the product did we then think it might be ready to go to a broader audience.
If you have a mechanism to listen to users, get something in their hands quite quickly and then get their feedback on it to run it back through a feedback loop, you're very unlikely to go wrong. It's actually very hard to go wrong if you have that feedback loop working really well.

Great names evoke without explaining

Humans only pay attention to what is new or what is different. So if you're looking at shoes and they're all black, black, black, black, and then the next pair of shoes is red, that's the first thing you focus on.
David PlacekFounder, Lexicon Branding 01:04:55

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