SPECIAL EPISODE: Why Products Grow (Part 2)

What does it actually take for a WordPress product company to grow year over year? In this special WP Product Talk panel, we’ll bring together product businesses that are successfully growing to unpack what’s working, what’s changed, and which strategies are driving their results. Rather than relying on generic advice, this conversation is grounded directly in real data from our recent Product Growth Survey. Host Matt Cromwell leads a candid discussion examining the survey’s key takeaways—analyzing how real-world WordPress businesses are navigating pricing, retention, acquisition channels, and strategic pivots, and what those trends reveal about what’s actually moving the needle in today's market.

Growth looks different for WordPress product businesses than it did a few years ago. Google organic search is becoming less dependable, AI is changing how people discover and build software, and simply adding more features isn’t necessarily translating into more sales. So what is working? In this special episode of WP Product Talk, Matt Cromwell, Katie Keith, Zack Katz, and Ian Misner dig into the real-world growth strategies behind three WordPress products that are growing right now: Nimesh Patel of Multidots, Mike McAlister of OllieWP, and Robin Pietersen of FooEvents. The conversation goes beyond marketing tactics to explore what product owners can actually control in a changing market. The guests share how retention and upsells are driving growth, why product-led growth and education can create powerful momentum, how meaningful new features and pricing changes can move the needle, and why customer support can become a source of product insight and revenue. They also tackle a bigger question facing WordPress businesses today: as AI makes it easier to build alternatives to traditional plugins, how can product companies become more valuable, differentiated, and resilient?

What happens when you accidentally become a WordPress plugin developer—and then keep going? Jonathan Hall of BerryPress joins WP Product Talk on September 9 with co-hosts Ian Misner and Matt Cromwell to share the winding path from an unplanned venture into plugin development 11 years ago to building multiple plugin businesses and eventually co-founding an international WordPress product company. Jonathan has developed dozens of plugins and learned plenty along the way about finding product ideas, marketing paid plugins, working with partners, and building a sustainable WordPress products business. We’ll also explore how AI and modern tools are changing plugin development and QA, along with the lessons Jonathan wishes he knew when he was just getting started. Whether you’re thinking about launching your first WordPress product or trying to figure out what comes next, this conversation offers a candid look at what it really takes to become a plugin developer and build products people want.

Your WordPress product website has a big job: it needs to build trust, explain your product, demonstrate its value, and ultimately convince visitors to buy. But what actually makes a product website work for a WordPress plugin or theme? On September 2 at noon Eastern, Imran Siddiq of Web Squadron joins WP Product Talk with co-hosts Matt Cromwell and Zack Katz to share his perspective on product website strategy, drawing from his experience building websites, teaching Elementor, creating WordPress content, and working with agencies and product businesses. We’ll dig into how to showcase features without bloated design, when live sandbox demos make sense, how to structure Free vs. Pro offerings, and why transparency can matter more than flashy marketing. If you sell a WordPress plugin or theme, this is a practical look at how your website can turn more visitors into confident customers.

Before a single line of code is written, the most important product decisions have already been made. Join us on August 12th as Zack Katz and Ian Misner welcome Brad Griffith of Buckeye Innovation for a conversation about why so many digital projects fail long before development begins. From unclear goals and undefined workflows to misunderstood user needs, Brad shares practical lessons from building websites, applications, and digital tools for purpose-driven organizations. Using a digital product strategy approach, Brad will explore how product teams can align strategy, design, and development to create solutions that solve real problems and deliver measurable outcomes. Whether you're launching a new WordPress product, planning a major feature, or evaluating your product roadmap, this episode will provide actionable insights to help you build the right thing before you start building anything at all.

Artificial intelligence is changing the role of software developers in ways that go far beyond code generation. On August 5, Katie Keith and Zack Katz welcome Ross Morsali to explore how AI research workflows are helping developers tackle problems that once seemed far outside their expertise, unlocking new opportunities for WordPress products and beyond. Ross shares how AI-guided research helped him completely rethink the indexing architecture behind Search & Filter by borrowing ideas from enterprise search systems and adapting them for WordPress. From there, the conversation expands into an exciting look at what's possible when developers use AI to venture into unfamiliar territory, including speech-to-text systems, custom language models, and other ambitious projects that would have once required years of specialized experience. Instead of asking AI to help us build faster, we should ask how AI can help us build things we never thought we could.

Most WordPress product founders start by building a plugin from scratch. Blake Whittle took a different path. As the owner of a WordPress agency managing hundreds of client sites, he acquired Infinite Uploads and Big File Uploads, inheriting an established product, an existing customer base, and a rapidly approaching Black Friday season. On July 29, Matt Cromwell and Ian Misner sit down with Blake to discuss what it really takes to buy and grow a WordPress plugin business. Blake shares lessons from evaluating the acquisition, navigating the critical first year of ownership, and balancing the demands of running both an agency and a product company. The conversation explores how an agency background can provide unique advantages when growing a software product, the challenges of taking over someone else's codebase and customers, and why acquisition may be a faster path to product ownership than building from the ground up. Whether you're an agency owner considering diversification or a product entrepreneur interested in acquisitions, this episode offers practical insights into buying, managing, and scaling an established WordPress plugin business.

What happens when you challenge one of the most established business models in WordPress? On July 22, Matt Cromwell and Zack Katz sit down with Rémi Corson, founder of SEOPress and creator of Milo, to discuss a different approach to plugin monetization: keeping the core product completely free while generating revenue through payments infrastructure and optional add-ons. After more than a decade at WooCommerce, Rémi set out to build a subscriptions plugin that avoids traditional feature paywalls and annual licensing. In this conversation, he shares the thinking behind Milo's monetization strategy, the tradeoffs of monetizing transactions instead of features, and what WordPress product owners can learn from building sustainable businesses around free software. Whether you're evaluating your own pricing model, considering a freemium approach, or wondering where the paywall should live, this episode offers practical insights into alternative WordPress plugin monetization strategies.

Every WordPress product owner has opinions about what drives growth, but what if your analytics told a different story? On July 15, Zack Katz and Katie Keith welcome Derek Ashauer, founder of Conversion Bridge and Sunshine Photo Cart, to discuss how conversion tracking data shapes the decisions behind his products and marketing strategy. Derek shares how he uses his own analytics tools to measure what actually moves the needle, from improving product features to identifying new growth opportunities. Along the way, he explains how real user data inspired his programmatic SEO strategy, why evidence consistently beats assumptions, and how WordPress product owners can make smarter business decisions by relying on the insights already available in their own websites. Whether you're refining your product roadmap, evaluating marketing efforts, or looking for sustainable ways to grow, this episode offers practical lessons in building with data instead of guesswork.

Are WordPress agencies approaching a point of no return? On July 8, Matt Cromwell and Ian Misner welcome Vito Peleg, founder of Atarim, to discuss the growing divide between agencies that are embracing AI and those struggling to keep pace. As automation reshapes how websites are built, managed, and maintained, agency owners face critical decisions that could determine whether they grow, adapt, or fall behind. In this conversation about AI for WordPress Agencies, Vito shares what he's seeing across the industry, from agencies using AI to scale faster than ever before to those losing ground as client expectations evolve. We'll explore whether retainers can survive the AI era, what work remains uniquely human, and how agency leaders can prepare for a future where intelligent agents become part of the team. Viewer Response Special thanks to M Asif Rahman, founder of WPDeveloper for this special key takeaways he shared on LinkedIn: