The best cloud infrastructure products share something in common: they make hard things feel easy without hiding the complexity. Tailscale does that better than anything I've used. This post is about why I'm joining as VP of Product to help figure out what comes next. Be sure to also read Tailscale Co-Founder & CEO Avery Pennarun's thoughts on my joining Tailscale.
My earliest introduction to computer networking was through gaming.
I was probably eight years old, visiting family friends for a holiday party. My friends took me to their basement to show something that amazed me: three computers running Warcraft II, all connected to each other. Three machines. One game. You could see your friend's army on your screen, then as it happened to me, get annihilated in real time.
That was my first LAN party. And it felt like magic.
A few years later, I learned the harsh reality of physics. We lived in the country-side with satellite internet and my attempts at playing Ghost Recon online were a disaster. Not because I was bad (okay, partly), but because my character was always half a second behind everyone else. That latency taught me something important: the distance between here and there isn't just miles. It's milliseconds that matter.
These were just the beginning of my networking experiences. Since then, I watched the Internet become simultaneously more connected yet more complicated. I was there for the container wars—Docker versus Mesos versus Kubernetes—debugging why pods couldn't reach each other across clusters. I've run service meshes in production, adding another layer of abstraction to solve problems created by the previous layer of abstraction. Every solution seemed to add new complexity: NAT traversal, firewall rules, PrivateLink, VPN configurations, DNS (the problem is always DNS!). We kept adding layers to solve problems created by earlier layers, until the simple act of getting two things to talk directly became surprisingly hard.
We have all accepted this tradeoff: you can have that LAN-party directness, or you can have global reach, but not both. The Internet gave us connection at the cost of complexity, latency, and layers upon layers of infrastructure between you and everyone else.
Enter Tailscale
I've been a Tailscale user since 2021. Not as a customer—as a hobbyist. I use it to connect all my personal devices: laptops, phones, tablets, my Synology NAS, and my Apple TV. I've looked at the open source code. I know it's built on WireGuard™. I understand how it works technically.
It still feels like magic every time and it isn't accidental.
It’s backed by real engineering with good taste. Tailscale makes the Internet work how the Internet should work. Instead of adding more layers at the top of the stack to hide the problems, Tailscale is building a secure, identity-aware network layer that makes the Internet feel like a LAN again.
Every device gets a certificate, a static IP address, a DNS name, and end-to-end encryption. It’s a flat network with built-in security & policy.
The numbers tell part of the story: over 20,000 business customers, more than a million monthly active users, and over three million monthly active devices. But what really tells it is the community. Look at Reddit or Discord — people don't just use Tailscale. They love it. They write blog posts about it. They tell their friends.
That's what happens when you make easy things easy again, and it’s something I wanted to be part of.
My new role
For the past four years, I led product for Kong's cloud platform, Konnect, scaling it from an early stage to their flagship product. That taught me what it takes to build developer infrastructure people and enterprises actually use.
Now I'm joining Tailscale’s executive team as VP of Product—a chance to shape a product and company that I believe will change how the world connects. I'll be working closely with the community and customers alongside our engineering, support, marketing, and field teams to figure out the future.
In a couple of weeks, I'm taking part in the Tailscale Winter Update. Sign up here to see what the team’s been building.
In the coming months, I'm building out teams across product management, growth, design, documentation, and developer education. If you want to work on problems like making enterprise networking feel as simple as consumer software, or helping developers understand what's possible when every device is addressable—I'd love to hear from you. Keep an eye on our careers page at https://tailscale.com/careers, or reach out directly on LinkedIn.
The Vision
A secure LAN, rebuilt at global scale.
When I started my career, networking meant connecting people to servers. Then mobile devices to the cloud. Then it was container to container. Now it's humans talking to agents, agents acting on behalf of users, and systems making decisions autonomously.
The question isn't just "can these things connect?"—it's "should they, under what conditions, and who gets to know about it?"I think Tailscale is uniquely positioned to answer that. Identity-aware networking isn't just a feature—it's the foundation for a world where machines and applications outnumber people on the network. When every connection knows who's on both ends, you can build things that aren't possible with IP addresses alone: granular access policies that follow users across devices, audit trails that actually mean something, zero-trust architectures that don't require a dedicated team to configure.
The mesh networks of the future, built on top of today's Internet. That's not just a product. It's a platform for whatever comes next.
That's the vision I'm here for.
