The Retention Gap: What WordPress Products Are Missing

Join us live on Wednesday, June 17, 2026, at noon Eastern for WP Product Talk as we welcome Gina Gindorf of Loya for an important conversation about why so many online stores struggle to turn first-time buyers into loyal customers. In "The Retention Gap: What WordPress Stores Are Missing," we'll explore practical lessons from real merchants and uncover what actually drives repeat purchases. If you're focused on sustainable growth, this episode will help you rethink how you approach Customer Retention for WooCommerce and why acquisition alone isn't enough. Gina joins co-hosts Matt Cromwell and Katie Keith to share insights on loyalty, post-purchase experiences, and low-friction strategies that can help WordPress store owners increase customer lifetime value.

AI is rapidly changing how support and troubleshooting work—but how do you introduce it without losing trust? In this episode, Drew Wilde, Director of Product Management at GoDaddy, joins us to share how his team built an AI Troubleshooter inside managed hosting for WordPress. Together, we explore how AI can proactively detect, diagnose, and resolve issues like downtime, performance degradation, and common WordPress errors—while still keeping humans in the loop. Drew also shares the product decisions behind balancing automation, control, reliability, and transparency. This episode offers practical lessons for WordPress product teams, hosting providers, plugin authors, and SaaS platforms looking to introduce AI-powered support responsibly—plus what surprised the team and what they’d do differently next time.

AI is rapidly reshaping the e-commerce landscape, but what does that actually mean for store owners and product builders? In this episode, Bryce Adams, founder of Metorik, joins us to discuss the current state of e-commerce and how AI is changing everything from analytics and automation to customer experience and growth strategies. Bryce shares what he’s seeing across thousands of stores, where AI is already making an impact, and where the hype still outweighs reality. Whether you're building eCommerce products, running an online store, or supporting clients, this conversation offers practical insights into how AI is shaping the future of eCommerce and what to pay attention to next.

What does vibe-coding look like for a WordPress website? In this episode, Andy Peatling joins us to explore a new approach to building with AI using Miles, an AI Design Partner for WordPress. Miles acts as your AI design partner, helping you create a fully custom block-based design in minutes, then refine it collaboratively. No templates, no page builders, and no shortcuts—just fast, flexible design powered by conversation. We dive into what vibe-coding really means for WordPress builders, how AI is changing the design workflow, and what this could mean for agencies, freelancers, and product teams. If you’re curious about the future of AI-assisted WordPress development, this conversation offers a practical look at what’s possible right now.

Curious how AI product teams are shipping faster and staying ahead? Join us for Lessons from Docsbot Week and Rapid AI Releases, where we unpack the power of Docsbot Week and what it teaches about modern AI product development. We’re joined by Josh Dailey, Chief Growth Officer at DocsBot.ai, to explore how rapid release cycles and build-in-public strategies are reshaping how products come to life. Live on Wednesday, May 6 at 12pm Eastern, Josh teams up with co-hosts Katie Keith and Zack Katz to share real-world insights on how AI startups ship products faster, validate ideas quickly, and build stronger customer relationships. If you're building WordPress AI products or exploring AI startup strategies, this conversation will give you practical ideas you can apply right away.

Running a product on the side sounds exciting, but it comes with real challenges. Our guest Yuri Gerasymov shares his 8-year journey of building and maintaining a product while working a full-time developer job and raising three kids. He will break down how to find ideas, how to get started, and what it takes to keep momentum without burning out. Whether you're a web developer or agency owner considering building your own product, this episode explores when to outsource, what to keep in-house, and how a side gig can either make you — or break you.

Matt "TK" Taylor, and Matt Kane from Cloudflare join WP Product Talk to discuss EmDash. Is it an opportunity for WordPress products to expand their reach, or a threat to our ecosystem? In this special episode of WP Product Talk recorded live at PressConf in Tempe, Arizona, hosts Matt Cromwell and Zack Katz sit down with Matt "TK" Taylor and Matt Kane from Cloudflare to unpack the buzz around EmDash — a new CMS positioned as a “spiritual successor” to WordPress. The conversation dives into how EmDash came to life, its modern architecture built on Astro, and whether this new platform represents a genuine opportunity for WordPress product creators or a potential threat to the ecosystem. From plugin sandboxing and security improvements to portability, hosting flexibility, and AI-native workflows, the guests share their vision for what a CMS built in 2026 should look like. The discussion also explores the business and community implications: plugin marketplaces, monetization opportunities, governance, and whether EmDash could spark a new “gold rush” for developers. With early community momentum, open-source ambitions, and strong interest from product builders, the panel weighs how EmDash might reshape the future of WordPress — or push it to evolve faster. If you're a WordPress product creator, agency, or developer wondering whether to pay attention to EmDash now or wait and see, this episode breaks down the risks, opportunities, and what to watch next.

Moving from client services to SaaS sounds like a technical challenge—but what if the real hurdle is market fit? In this episode, Matt Schwartz, Founder of Checkview, shares how his biggest lessons weren’t about code, but about deeply understanding customers, shaping a roadmap, and questioning assumptions about where agencies truly find value. As he transitioned from services into product, Matt discovered that deciding what to ship—and just as importantly, what not to—was far more complex than building the product itself. Join co-hosts Zack Katz and Katie Keith on April 1 at Noon Eastern / 6pm CET as they unpack the realities of customer discovery, SaaS vs. plugin positioning, education-driven marketing, and creating meaningful early feedback loops. This conversation is especially relevant for WordPress product founders and agency owners considering the leap into SaaS, offering honest insights into the messy, high-stakes work of finding real market fit before it’s too late.

Behind every “simple” website is a complex WordPress agency tech stack—often made up of 10 to 30 disconnected tools for hosting, security, backups, reporting, and more. In this episode, Emmanuel Khoury, Co-founder of WPStaq, pulls back the curtain on what’s really happening inside agencies and why fragmented systems lead to higher costs, slower delivery, stressed teams, and unhappy clients. We’ll explore what happens when agencies consolidate their workflows, reduce tool sprawl, and rethink how their WordPress agency tech stack is structured. If you build products for agencies—or run one yourself—this conversation will help you understand where operational friction lives and how unifying tools can reduce support noise, overhead, and churn while improving client outcomes.

Join us for an upcoming episode of WP Product Talk titled “All about Growth Marketing” with Stuart Brameld, founder of GrowthMethod, on March 18 at 6:00 PM CET. Matt Cromwell and Ian Misner will dig into what growth marketing for software products really looks like when you’re trying to build traction in a competitive market. This conversation is built for WordPress product owners who want clearer ways to attract, convert, and keep customers without wasting time on random tactics. If you want practical ideas for sustainable growth, this is one live episode you won’t want to miss.