About this episode

In this episode, Matt Medeiros interviews Jesse Brede about the evolving landscape of WordPress agencies and the integration of service and software in 2026.

What does it actually take to run a healthy WordPress agency in 2026 — when AI is rewriting the rules, clients expect more strategic value, and the "build a site, ship it, move on" model no longer pays the bills? In this episode of Breakdown, Matt Medeiros sits down with Jesse Brede, founder of Austin-based Lion's Share Digital and former fourth employee at WP Engine, to unpack what a modern agency looks like when service and software start to merge. Jesse shares the playbook behind LionShare's growth: a paid discovery process that earns client trust before a line of code is written, a retainer-first model that smooths out the feast-or-famine cycle, and a custom internal dashboard ("LSD OS") designed to give clients real visibility into their sales, operations, and lead flow. Along the way, he and Matt dig into how AI is actually showing up in agency work — not as a replacement for craft, but as a layer underneath it. In This Episode Why Lion's Share keeps WordPress at the center of its agency stack — and where Jesse thinks the platform still needs work The "service + software" thesis: why being just a service agency may not be enough going forward Building LSD OS, an internal…

People in this episode

Host: Matt Medeiros

Guest: Jesse Brede

Topics covered

• WordPress agency
• AI in agency work
• service and software integration
• client trust
• business intelligence dashboard
• retainer model
• paid discovery process

Keywords

• WordPress
• agency growth
• AI
• business model
• client engagement
• dashboard
• retainer
• discovery process

Mentioned in this episode

Organizations: Lion's Share Digital, WP Engine

Products: Claude, Perplexity, ChatGPT

Places: Austin

More episodes of Breakdown - A Gravity Forms Podcast

• How WordPress and Gravity Forms Became the Ultimate Nonprofit Tech Stack · July 6, 2026 · 27 min

Explore listener stats, chart rankings, contacts and more on the Breakdown - A Gravity Forms Podcast podcast page.