Within WordPress

In this episode of Within WordPress, I sit down with Rodolfo Melogli to talk about his path from growing Business Bloomer into one of the best-known WooCommerce resources to now launching Checkout Summit, a dedicated in-person WooCommerce conference in Palermo, Sicily, on April 23–24, 2026 After years without a WooCommerce-focused event since WooConf 2017, Checkout Summit feels like a big moment. Rodolfo explains why now is the right time, how AI has changed content-led growth, and why he is betting on something far more human: personal brand, real relationships, and community. We dig into the thinking behind the event, from its intentionally small size of just 150 attendees to the 12 carefully selected WooCommerce talks, practical breakout sessions, and all-inclusive format designed to keep people together and conversations flowing. The goal is simple: less conference chaos, more meaningful connections, better conversations, and real business outcomes. If you care about WooCommerce, events, community, and where growth is heading next, this episode is for you. There are still some tickets left at checkoutsummit.com. 00:00 Podcast Welcome Guest00:54 WooCommerce Origins 201101:42 Choosing Ecommerce Platforms02:50 From Rome To Ireland04:05 Life In Sicily Food Heat06:12 Roman Identity Accents07:37 International Clients Only11:14 Italy Business Reality14:57 WooCommerce Fork Story15:55 Why WooCommerce Clicked18:24 Blog Snippets Take Off20:08 AI Changes Content Game22:50 Viral Tech Fix Post24:07 Why Sicily Summit25:28 WooCommerce Events Gap27:05 Small Conference Vibe32:35 Building In Public36:39 Unique Event Format43:00 Tickets And Timing45:01 Speaker Selection Strategy49:21 Wrap Up And Links

In this episode of Within WordPress, I talk with Jason “JK” Konen of WP Engine about Newsroom, a WordPress-based publishing platform built for large editorial teams. We explore what makes high-volume newsrooms different from typical blogs, where WordPress workflows start to break down at scale, and how Newsroom aims to solve those problems. JK explains how the platform gives different team members, from editors to SEO specialists to media teams, the tools they need without forcing everyone into the same interface. We also talk about collaboration, publishing guardrails, and the role of checklists in helping teams meet editorial and accessibility requirements before anything goes live. That includes practical AI-assisted features, such as helping generate alt text, with a focus on supporting workflows rather than replacing journalism. JK shares how Newsroom grew out of work with UK agency Big Bite in late 2023, and why WP Engine sees it as a way to help publishers move away from patched-together processes and toward a more structured, scalable editorial workflow. 00:00 Welcome and Guest Intro 01:06 Jason’s Tech Journey 03:28 What Is Newsroom 06:32 Why Build This Suite 09:58 Who It’s For 11:45 Agency Pain and Foundation 14:36 Role Based Interfaces 22:37 Workflow Guardrails 25:50 AI Assist Not Replace 29:19 What’s Next With AI 32:17 AI and Content Data 37:58 Daily Topic Suggestions 42:01 Experiment Fast Mindset 42:31 Beyond Generative AI 43:07 AI Imagery Feels Off 45:26 Visual Aids With Napkin 46:37 AI Wild West Phase 49:28 Rethinking Publishing Strategy 50:54 Newsroom Feature Highlights 52:57 Collaboration Mode Philosophy 56:11 How To Get A Demo 59:18 Meet Jason Conan 01:01:40 What Newsroom Solves 01:08:41 Building For Enterprise Teams 15:32 Role Based Interfaces 18:09 SEO As Separate Job 21:38 Workflow Guardrails 01:20:59 SEO Checklist Wins 01:23:03 Accessibility Before Publish 01:24:01 Building With AI 01:28:13 Agentic Search Future 01:30:38 Data Driven Suggestions 01:36:09 Daily Topic Briefings 01:41:46 Practical AI Uses 01:48:20 Newsroom Feature Highlights 01:51:42 Collaboration When Needed 01:54:23 Get a Demo 01:55:04 Closing Thoughts

In this episode of Within WordPress, we sit down with Carole (CloudFest) and Mark Weisbord (CEO of Greyd) to explain what is changing at CloudFest this year, and why it matters for agencies and WordPress businesses. The headline is the launch of the WordPress Business and Agency Summit on the Monday before the main CloudFest event. We position it as a connector between the CloudFest Hackathon and the main CloudFest conference, and as a deliberate step toward giving agencies and WordPress businesses a more relevant, more pragmatic, more commercially useful program than the traditional “WordPress Day” format. We unpack the difference between WordCamps and CloudFest. WordCamps remain community-first, volunteer-driven, and primarily focused on education and connection inside the WordPress community. CloudFest is a for-profit, cloud and hosting industry conference with a very different scale, structure, and mission, and it can build a dedicated business-focused layer around WordPress without trying to turn WordCamps into something they were never designed to be. This year’s Summit expands the former WP Day into a full-day, two-track program, adds an exhibition area, and targets roughly 800 attendees in a more intimate setting inside a much larger 10,000+ person event. From Mark’s perspective, if we want growth and new partnerships, we need to attract agencies outside the WordPress community, and we need content that connects to direct business impact. That means talks about sales, pricing, go-to-market, agency operations, maintenance revenue, and what it really takes to move from agency work into becoming a product company. We also talk about the CloudFest Hackathon as a uniquely valuable environment for multi-day collaboration and deeper conversations that rarely happen at faster-paced conferences. Carole connects that to a broader goal: cross-CMS collaboration and strengthening the open web, so we do not end up with a future where a handful of platforms dictate where and how people can publish. We close with practical attendance advice, a reality check that the Hackathon is already fully booked, and the key dates for the Summit and the main CloudFest event. 00:00 – Cold open: editing workflow and “wave” marker for cuts00:01 – Welcome and setup: two guests, and why this episode is different00:02 – Carole: WordPress community background and CloudFest involvement00:03 – What CloudFest is: scale, audience, and Europa-Park as the venue00:04 – “Everything is different this year”: why we are doing this episode00:05 – The new WordPress Business and Agency Summit: where it fits in the week00:06 – Mark Weisbord (Greyd): the missing business layer in WordPress events00:07 – From “WP Day” to a bigger Summit: what changes operationally00:08 – Two tracks, full day, and a dedicated exhibition area00:09 – Why this format matters: connecting agencies, partners, and real-world solutions00:11 – WordCamps vs CloudFest: why they serve different purposes00:12 – Sponsor reality: ROI pressure, leads, and reaching agencies outside the bubble00:13 – Content shift: business impact over general tech presentations00:14 – WordCamps still matter, but they are not the vehicle for everything00:16 – Biggest change: bring in agencies outside WordPress, plus an entertainment factor00:18 – CloudFest vibe: opening party, Lords of the Uptime, and the venue experience00:23 – Practical advice: stay multiple nights for Summit welcome + opening party00:25 – Hackathon value: multi-day conversations and real collaboration time00:28 – Hackathon evolution: cross-CMS collaboration and protecting the open web00:33 – Why agencies benefit: broader ecosystem exposure than a WordCamp context00:36 – What the Summit covers: sales, pricing, playbooks, productizing, maintenance00:40 – How Summit pillars extend into the main event: maintenance, security, performance00:42 – Why WordCamps and business events should stay structurally distinct00:44 – What is still missing at WordCamps: business education as part of opportunity00:46 – Scale reassurance: 800-person Summit inside a 10,000+ event, with space to breathe00:48 – Theme park reality: downtime, gyms, and the week’s rhythm00:51 – Hackathon is fully booked; when applications reopen00:52 – Dates: Summit and CloudFest main event, closing

Jono Alderson, technical SEO consultant and WordPress developer known for work at Yoast, discusses web standards, performance, and accessibility. He explains why JavaScript-only sites often fail and contrasts server-rendered WordPress with headless approaches. They explore AI as a tooling extension, caching, edge strategies, and practical fixes like responsive image handling.

In this episode, we dive into the world of WordPress with Elliott Richmond, a seasoned web developer who has been crafting websites for over 20 years. Elliot discusses his journey, from becoming a developer to running his software company with his wife, Rachel. We also explore his passion for teaching WordPress through YouTube and how he balances it with his unique side hustle: running a pizza delivery business. Learn how Elliot marries his coding skills with entrepreneurship and community engagement, offering a comprehensive view of his multifaceted career. 00:00 Introduction and Guest Welcome00:38 Elliot's Background and Experience02:52 YouTube and Teaching WordPress05:17 Balancing Creativity and Technical Skills13:50 AI in Development and Content Creation27:14 The Impact of Technology on Social Interactions28:16 Balancing Work and Personal Life28:43 The Evolution of a Software Business31:10 Challenges and Benefits of Full Site Editing40:18 The Pizza Business Journey43:46 Mediterranean Influences and Culinary Passion48:12 Licensing and Expanding the Pizza Business53:28 Conclusion and Future Plans

Join us as we delve into the importance of web accessibility with Amber, the CEO of Equalize Digital. Discover her journey, the significance of accessibility in web development, common assistive technologies, and the current state of accessibility in WordPress websites. Amber also shares insights from their annual page builder accessibility report, the role of education in improving digital accessibility, and how developers can integrate accessibility into their tools. This episode is a must-watch for anyone looking to make their websites more accessible and inclusive.

Imran Siddiq, a UK-based YouTuber from Web Squadron, lends his insights as a web designer and content creator. He discusses the idea of echo chambers in the WordPress community, addressing how dominant voices can overshadow diverse perspectives. Imran reflects on his journey from the NHS to web design, the evolving role of AI in coding, and the importance of inclusivity at WordPress events. He emphasizes the need for innovative content that fosters genuine connections and encourages creators to explore beyond WordPress's limits.

Kevin Ohashi, Founder of Review Signal, shares his expertise on benchmarking WordPress hosting. He reveals how his rigorous testing methodologies evolved and the challenges in maintaining an unbiased review platform in an affiliate-driven landscape. The conversation highlights the impact of open-source tools like K6 and the ethical dilemmas in the review process. Kevin also recounts his unexpected adventure acquiring the domain portugal.com, blending his tech passion with personal travel experiences, making this a blend of insight and storytelling.

Welcome to this episode of 'Within WordPress' featuring Matt Cromwell, co-founder of Give WP and senior director of customer experience at Stellar WP. Join us as we explore Matt's journey in WordPress, his various roles, and his highly insightful views on product ownership and AI implementation. Matt discusses his podcast, WP Product Talk, the insights it brings to WordPress product owners, and a special upcoming presentation at WordCamp US. Dive into an engaging discussion on the implications of AI on performance, security, and the future of WordPress. Don't miss this thought-provoking conversation!

In this episode, we are joined by Juan Hernando, who shares his extensive experience in the WordPress community. We explore Juan's journey from a front-end web developer to his current role in community engagement at Weglot and as a program manager on the global community team at WordPress.org as well as his involvement with WordCamp Europe. Juan discusses the challenges and rewards of transitioning from client work to focusing on community and events, highlighting the importance of localization and translation in today's fast-paced digital landscape. He also provides insights into how Weglot leverages AI to enhance website translations and maintains the authentic tone of content across different languages. This episode is a deep dive into the complexities and intricacies of managing large-scale WordPress events and the crucial role of sponsorships in sustaining community contributions. Tune in to learn more about the evolving trends in WordPress and the pivotal role of community and collaboration in driving innovation.