In this episode of The SaaS Revolution Show, host Alex Theuma is joined by Matt Mullenweg Co-founder at WordPress and Founder and CEO at Automattic.

Matt shares his biggest lessons from a decade as CEO at Automattic and his biggest learnings from the journey to $500M. 

You’ll learn: 

  • The mindset and mission behind Automattic.
  • How AI is reshaping the WordPress ecosystem.
  • Key lessons from scaling to $500M ARR.
  • What his ‘ideal’ work week looks like.
  • How he stays motivated as CEO.

Watch below (or listen) or read on for key takeaways: 

A mission to democratize publishing, commerce, and messaging

Matt co-founded open-source publishing platform WordPress when he was just 19 years old. From there, he moved to San Francisco and founded Automattic a couple of years later to create SaaS products around open source. 

Today, Automattic’s mission remains simple, to democratize publishing, commerce, and messaging. It does this through a suite of SaaS products.

  • Publishing: WordPress.com, with solutions for SMBs (Pressable) and enterprises (WordPress VIP). 
  • Commerce: WooCommerce, an “open source Shopify” used to sell $30B of goods and services every year.
  • Messaging: Beeper (in beta ), which brings all of your messaging platforms under one app, and Tumblr, the microblogging site with over 100M+  monthly active users. 

WordPress powers 40% of websites on the internet and supports a $10B dollar ecosystem. Automattic is a globally distributed company operating at over $500M ARR. Even after a decade in post, Matt remains enthusiastic about his work, with his eyes set on even bigger milestones. 

Bringing AI into the WordPress ecosystem

For Matt, AI brings exciting opportunities to help more users adopt WordPress successfully.

He talked about two main approaches:

1. AI site builder

“WordPress is a power tool in a lot of ways. It’s got a ton of functionality. Our goal is always to make simple things intuitive and complex things possible. But with software design, that’s always a work in progress.”

On the day of the interview, WordPress.com launched its AI site builder. Rather than rushing a release, the team took time to build something that “teaches people how to use WordPress as the AI builds it”.

“We’ve got this incredible block editor in WordPress called the Gutenberg Editor. You can just talk to it and say, change the colors, change the fonts, change the images, make more starter text. It can do what people would have needed to hire a developer for.”

2. Security at scale

WordPress as a platform has over 60,000 plugins–with each one, the code quality varies. So, while the WordPress code base is very secure, plugin vulnerabilities cause security issues. 

“When you see a headline ‘30,000 vulnerable WordPress sites’, it’s because of a plugin that 30,000 sites have installed. AI is going to allow us to find and fix those bugs way better than before. I’m looking forward to that improving the overall security for millions of WordPress sites.”

Lessons in scaling to $500M

Scaling a company to $500M is a rare milestone but with products at various stages of maturity, Matt’s learnings are relevant to founders at any stage of growth.

  1. Product quality is incredibly important: Use feedback loops and direct support to fix issues and create lifelong fans. 
  2. Don’t underestimate word of mouth: One passionate user can bring in dozens more–guiding them through onboarding and helping them find time to value more quickly.
  3. ‘Dogfood’ your own products: Experiencing your product as a user is a great way to stay close to your customers.
  4. Stay really close to your customers (for as long as you can): Whether by hosting events and workshops, or jumping on support tickets–how you interact with customers can be your key differentiator.

A week in the life of a $500M CEO

As Automattic has scaled, the biggest shift in Matt’s role has been less hands-on coding and more leadership and strategy. 

Now, his ‘ideal’ week is split into three: 

  1. People: Hiring, HR, and performance management.
  2. Product: Product reviews, architecture meetings, and business strategy.
  3. ‘CEO stuff’: Fundraising, board management, and those unpredictable high-stakes moments only the CEO can handle.

Staying motivated after 10+ years as CEO

Many CEOs step back after ten years but Matt’s still all in. Here’s what keeps him energized:

  • AI innovation: Code that took 8-10 hours can now take 20-30 minutes. These advances offer new opportunities for Automattic.
  • Hiring strong executives: Leaders who can give their full time to specific areas of the business means Matt can focus where he has the most impact.
  • Keep learning: Matt believes that people are only limited by their own ambition and curiosity. He takes time to read and listen to podcasts to make sure he’s always learning.

Hear more from Matt at SaaStock USA (13-14 May)

Matt is joining our stellar lineup of SaaStock USA Founderpath Center Stage speakers including Alina Vandenberghe (Chilipiper), Savneet Singh (PAR Technologies), and Neha Sampat (Contentstack).

💥 1,500 SaaS founders, execs, and investors. 2 days. 1 city.

If you’re serious about scaling your SaaS in 2025, you need to be there.

Tickets are selling fast! Get yours now.