October 23rd 2025
Joining Plain as Head of Community
After a decade leading support teams, I’m switching sides – from buying tools to building them.
This is a new chapter for me. I’ve spent years inside support orgs, evaluating tools, fighting budgets, and trying to make systems work for people.
Now, I get to help build the kind of system I always wished existed. A new way to do support.
The Problem I've Been Obsessed With
If you know me, you know I love talking about the future of customer support. Exploring new approaches. Challenging conventional metrics. Changing the narrative.
I've spent my career proving that support isn't just a reactive function. It didn't matter if I was leading support at Airbnb, at Loom, or advising startups – the challenge is always the same.The best experiences happen when workflows and tools adapt to teams, not the other way around.
At Loom, we saw it first-hand: free users who had great support interactions were far more likely to upgrade. Our team was actively creating business value. But the tools never caught up.
Everything took time. Everything needed engineering help.
The tools we used just weren’t built for how we actually wanted to operate.
What Support Teams Actually Want
I've always wanted a platform that works the way support teams actually work. Not one that tells you how you should.
Most tools come with rules: Here’s your workflow, here’s how tickets move through the system.
Most systems feel like work to use: Here’s another button, here’s yet another slow-loading page, here’s yet another process.
Most platforms see AI in fairly simplistic terms: Deflect tickets, reduce headcount, replace humans.
I wanted the opposite.
A system where you can design your own workflows, integrate with your stack, and model your customer data the way you actually think about it. Something that puts the team in control.
A tool that’s designed for work, instead of feeling like work. One that lets you work at the speed of thought, that is enjoyable to spend time in, and makes working with customers easier and faster.
AI that engages customers, rather than deflecting them – and serves the humans that serve customers by making them faster, smarter, and able to focus on the work that matters most.
It’s what support teams actually want.
Plain Feels Like Modern Support
When I met Simon and Matt, Plain’s co-founders, something clicked. They shared my belief that support software should be flexible, designed for the people doing the work, and engineered with AI at the core.
They weren’t polishing the same old model. They were rethinking how tomorrow’s support teams will work, with AI at the core.
Plain is building for the people doing the work, not just their managers. As one of our customers put it, it’s “designed for actual humans.”
Because modern support shouldn’t feel like work – it should feel like a way of working.
From Managing Support to Designing It
This is the first time I won't be managing a support team directly.
Instead, I’ll be working at the intersection of product and community, helping Plain's customers - teams like Ashby, Cursor, n8n, and Granola - design exceptional support operations.
These companies serve millions of users, and part of our mission at Plain is to raise the bar for what great support feels like.
My job is to bring the community’s perspective into Plain - including, and especially, the challenging viewpoints. My job is to help build a product that reflects a movement, not just our own opinions.
That’s also why everyone at Plain works directly with customers. When you're building a support platform, there's no hiding from your own product. We live what we sell.
For me, this role is a way to take everything I’ve learned and share it beyond a single company. To help more teams design thoughtful, efficient, and human support systems, and to build the infrastructure that makes that possible.
It’s a new chapter, and a chance to help shape what the future of customer support looks like.
Want to book some time with me?