WordPress to Shopify: Smart Expansion or Expensive Distraction?

Should your WordPress product business expand to Shopify? For plugin and SaaS owners, Shopify can look like a compelling opportunity to reach a new market—but expanding to another ecosystem also brings new technical challenges, customers, competitors, marketplaces, and support demands. On October 14, Katie Keith and Ian Misner will dig into the realities of going from WordPress to Shopify, exploring when expansion makes strategic sense, what product owners need to consider before making the move, and where the biggest opportunities and risks lie. If you’re considering taking your WordPress product beyond its current ecosystem, this conversation will help you think through whether Shopify is a smart next step—or an expensive distraction.

Pricing is one of the biggest growth levers for a WordPress product business, yet it’s easy to get wrong. Price too low and you leave revenue on the table or attract customers who aren’t a great fit; price too high and you may limit the market you can reach. Jason Cohen, founder of WP Engine, returns to WP Product Talk with co-hosts Zack Katz and Katie Keith to explore how product businesses can use pricing strategically to drive sustainable growth. Drawing from his experience growing WP Engine and advising startups, Jason will share practical frameworks and real-world examples for thinking about pricing, positioning, customer segments, and growth. We’ll explore why price isn’t simply about maximizing margin, how changing your pricing can change the market you attract, and how to find the pricing strategy that gives your WordPress product room to grow.

Influencer marketing can be powerful for tech products, but the playbook isn’t quite the same as it is for fashion, lifestyle, or consumer brands. On September 30 at noon Eastern, Britt Celata of Automattic joins WP Product Talk with co-hosts Katie Keith and Matt Cromwell to take us behind the scenes of building an influencer marketing program for a tech product, using WordPress.com’s “Stories Worth Hosting” campaign as a real-world case study. Britt will share how the team partnered with creators across different niches to tell authentic product stories while balancing brand and performance goals. We’ll explore how to measure the impact of creator partnerships beyond vanity metrics, what surprised the team along the way, and which lessons product marketers can apply to their own influencer and creator strategies. For WordPress product businesses looking to build trust, reach new audiences, and tell better product stories, this conversation offers a practical look at what creator marketing can really accomplish.

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.