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 business intelligence dashboard, as a proof of concept for clients
• How Jesse's team uses Claude, Perplexity, and ChatGPT — and why a human layer still sits on top of everything
• The paid discovery process: 3–5 meetings, real deliverables, and how it filters out the wrong clients
• Why monthly retainers and site care plans were the real turning point for the agency
• Capturing meeting transcripts with Fathom and feeding them back into AI for tasks, scope, and follow-up
• A standout Gravity Forms use case: a scored security quiz feeding gated whitepapers and Salesforce
• A preview of what's coming for Gravity Forms with the new WordPress Abilities API

About Jesse Brede

Jesse Brede is the founder of Lion's Share Digital, a full-service digital media agency in Austin, Texas, where he and his team handle everything from brand strategy and WordPress development to PPC, SEO, and Shopify builds. Before launching LionShare in 2011, Jesse was the fourth employee at WP Engine — giving him a front-row seat to the rise of managed WordPress hosting. When he's not running the agency, he's deep in the electronic music world as a DJ and record label owner.

Connect with Jesse:
Website: lionssharedigital.com

• LinkedIn: https://www.linkedin.com/in/jessebrede/