Maya Kaczorowski, Chief Product Officer at Tailscale, joins Corey on Screaming in the Cloud to discuss what sets the Tailscale product approach apart, for users of their free tier all the way to enterprise. Maya shares insight on how she evaluates feature requests, and how Tailscale’s unique architecture sets them apart from competitors. Maya and Corey discuss the importance of transparency when building trust in security, as well as Tailscale’s approach to new feature roll-outs and change management.About MayaMaya is the Chief Product Officer at Tailscale, providing secure networking for the long tail. She was mostly recently at GitHub in software supply chain security, and previously at Google working on container security, encryption at rest and encryption key management. Prior to Google, she was an Engagement Manager at McKinsey & Company, working in IT security for large enterprises.Maya completed her Master's in mathematics focusing on cryptography and game theory. She is bilingual in English and French.Outside of work, Maya is passionate about ice cream, puzzling, running, and reading nonfiction.Links Referenced:
Tailscale: https://tailscale.com/

Tailscale features:
VS Code extension: https://marketplace.visualstudio.com/items?itemName=tailscale.vscode-tailscale 
Tailscale SSH: https://tailscale.com/kb/1193/tailscale-ssh 
Tailnet lock: https://tailscale.com/kb/1226/tailnet-lock 
Auto updates: https://tailscale.com/kb/1067/update#auto-updates 
ACL tests: https://tailscale.com/kb/1018/acls#tests 
Kubernetes operator: https://tailscale.com/kb/1236/kubernetes-operator 
Log streaming: https://tailscale.com/kb/1255/log-streaming 


Tailscale Security Bulletins: https://tailscale.com/security-bulletins 
Blog post “How Our Free Plan Stays Free:” https://tailscale.com/blog/free-plan 
Tailscale on AWS Marketplace: https://aws.amazon.com/marketplace/pp/prodview-nd5zazsgvu6e6 

TranscriptAnnouncer: Hello, and welcome to Screaming in the Cloud with your host, Chief Cloud Economist at The Duckbill Group, Corey Quinn. This weekly show features conversations with people doing interesting work in the world of cloud, thoughtful commentary on the state of the technical world, and ridiculous titles for which Corey refuses to apologize. This is Screaming in the Cloud.Corey: Welcome to Screaming in the Cloud. I’m Corey Quinn, and I am joined today on this promoted guest episode by my friends over at Tailscale. They have long been one of my favorite products just because it has dramatically changed the way that I interact with computers, which really should be enough to terrify anyone. My guest today is Maya Kaczorowski, Chief Product Officer at Tailscale. Maya, thanks for joining me.Maya: Thank you so much for having me.Corey: I have to say originally, I was a little surprised to—“Really? You’re the CPO? I really thought I would have remembered that from the last time we hung out in person.” So, congratulations on the promotion.Maya: Thank you so much. Yeah, it’s exciting.Corey: Being a product person is probably a great place to start with this because we’ve had a number of conversations, here and otherwise, around what Tailscale is and why it’s awesome. I don’t necessarily know that beating the drum of why it’s so awesome is going to be covering new ground, but I’m sure we’re going to come up for that during the conversation. Instead, I’d like to start by talking to you about just what a product person does in the context of building something that is incredibly central not just to critical path, but also has massive security ramifications as well, when positioning something that you’re building for the enterprise. It’s a very hard confluence of problems, and there are days I am astonished that enterprises can get things done based purely upon so much of the mitigation of what has to happen. Tell me about that. How do you even function given the tremendous vulnerability of the attack surface you’re protecting?Maya: Yeah, I don’t know if y