Nick Caldwell, Twitter's VP of Engineering

11/18/20 • 37 min

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In this episode, we talk with Nick Caldwell, the VP of Engineering at Twitter.

Nick joined Twitter over the summer, after a long career building enterprise products. He now leads a team of 700 engineers on the consumer side. That presented him with a very different set of daily challenges.

“Enterprise versus consumer is a very different mindset and approach that I see people struggle with if they aren't comfortable with it. But enterprise, if done correctly, is more like chess. Consumer products are just gambling, as far as I can tell. It's gambling plus, it's maybe like fantasy football,” says Nick.

Nick was hired at Twitter because he’s really good at managing teams and setting product roadmaps. He got his start at Microsoft, where he worked for more than 15 years leading the data platform organization.

Quentin and Steve spoke with him about those early days working in enterprise -- and how they compare to his roles at Reddit and Twitter, which have very different cultures.

This podcast is produced by Post Script Audio in collaboration with General Catalyst.

In this episode, we talk with Nick Caldwell, the VP of Engineering at Twitter.

Quentin and Steve spoke with him about those early days working in enterprise -- and how they compare to his roles at Reddit and Twitter, which have very different cultures.

This podcast is produced by Post Script Audio in collaboration with General Catalyst.

Previous Episode

Intuit CTO Marianna Tessel on AI-First Software

In this episode, we speak with the Chief Technology Officer of Intuit, Marianna Tessel.

Marianna is a seasoned tech executive who oversees all of Intuit’s product engineering, data science, information technology, and information security teams. Marianna previously led engineering teams at Docker, Ariba and VMWare. She landed at Intuit in 2017.

Intuit makes a range of software products for taxes and business management, including TurboTax, Quickbooks and Mint. And she’s leading thousands of engineers in AI-first development to make products easier, cleaner, and more intuitive.

“I think you're going to start rewriting applications with this AI first. And just the way the world of apps re-imagined itself for mobile, it has to reimagine itself for AI. Which probably is an even more extreme transformation,” says Marianna.

Quentin and Steve spoke with her about engineering products in the midst of a pandemic that is crushing many of the small businesses Intuit serves.

This podcast is produced by Post Script Audio in partnership with General Catalyst.

Next Episode

Dropbox’s Akhil Gupta on ‘Brutal Prioritization’

This week’s episode is all about magic pockets, nickels, cupcakes, and brutal prioritization. It’s a conversation with Akhil Gupta, the general manager and VP of enterprise at Dropbox.

Before that, he was the VP of engineering and the head of infrastructure -- running a 500-person engineering team that helped create the technical foundation for the Dropbox we know today.

Steve and Quentin will talk with Akhil about how Dropbox scaled reliably from 2,000 users in 2008 to hundreds of millions of registered users today.

Back in 2012, when Akhil first joined the company from Google, there were 30 engineers. Dropbox had emerged as a leading cloud storage provider, but it faced a clear choice: should it build its own storage or rely on the public cloud? Enter "Magic Pocket."

And that technical challenge forced him to adopt a simple philosophy: brutal prioritization.

“My anxiety always is when you get too many people in a company, you start creating problems and you start losing focus because you have so much new energy, you are growing fast and you can say, let me solve every single problem. So I wanted to give a signal to the team saying, we need to always prioritize. And prioritization is hard, prioritization is painful. And hence the word brutal,” says Akhil.

This podcast is produced by Post Script Audio in collaboration with General Catalyst.