From Industry Veteran to Global Expansion Lead

WordPress is no longer ignoring global expansion efforts. It is no longer a future agenda item; rather, it is a current, actionable step motivated by people who know how to make a service work. One of the key figures behind this effort is James Grierson, whose decades-long career spans hosting, domains, online marketing, and large-scale SaaS operations.

In 2026, Grierson is today’s Head of Global Expansion at Automattic, but his experience shapes his perspective and exceeds what his title conveys. Prior to Automattic, Grierson served as COO of Bluehost. That experience running a large, traditional hosting organization gave him a ground-level view of infrastructure, customers, growth pressures, and the realities of operating at scale.

Within Automattic, he eventually took leadership of Jetpack, one of the most widely used products, and subsequently moved to a more outward-facing role to address territories where WordPress has not fully penetrated.

That history is crucial because, unlike most companies, global expansion for Automattic is not solely a marketing opportunity. It is being treated as a unique combination of product, market, and infrastructure challenges.

Split the World

When James initially spoke with Automattic founder Matt Mullenweg about the position, the parameters were deliberately wide.

“Matt basically told me to split the world into English and non-English—and own everything non-English for Automattic.”

That directive set the tone. It was not about translating dashboards or U.S.-centered assumptions about other regions. It was an expansion of understanding of how people in different locations engage with the internet and how that translates into the product.

What Global Expansion Actually Requires

It also means understanding how people socialize and communicate, which communication and payment channels prevail, what laws or frameworks govern, and what infrastructure is available. These characteristics are often disregarded, yet they critically define whether a product will succeed or fail.

“Global expansion isn’t just about translation. It’s about understanding how people communicate, how they pay, and how they actually use the internet in their country.”

These differences add up quickly. There is a huge gap between payment expectations in Brazil and India. In Indonesia, the data residency requirements shape hosting choices in ways that other global players often miss. In many regions, mobile-first usage isn’t a trend—it is the standard, even in places that lack reliable access to high-end smartphones.

Expanding Beyond WordPress Alone

This impacts much more than WordPress itself. Automattic owns Jetpack, WooCommerce, WordPress.com, and other apps that are continually added to its portfolio. Each of these products faces new challenges in different markets and must adapt to evolving expectations for commerce, connectivity, and user behavior. His primary aim is to deliver that localized feeling, rather than to offer a product that has simply been imported.

A Small Team, Focused on Real Signals

Although this is a significant responsibility, the global expansion team is deliberately small. Instead of trying to be in every country at once, the plan is to focus on markets where genuine activity is already occurring. They look at historical signups, product usage patterns, and spontaneous adoption to determine where to allocate resources in the future.

How AI Accelerates Market Research

AI has become one of the most significant advancements in this area. James utilizes AI in market research, competitive analysis, and early-stage discovery. What used to take weeks in outreach and research fragmentation can now be accomplished in hours. This allows teams to progress rapidly without omitting due diligence.

“AI has completely changed how fast we can do market research. What used to take weeks now takes hours.”

That speed, however, does not replace human judgment. AI provides a starting point, surfacing patterns, summarizing regulations, and outlining competitive landscapes, but the work still requires validation.

“AI doesn’t replace the work—it gets you to a solid first understanding much faster. You still have to validate everything.”

Lessons From Decades in Hosting

Jame’s views on the hosting industry are reflected in his plans for expansion. Having spent nearly two decades in hosting, he firmly believes that the technical barriers to entry are still very low. Infrastructure that used to be built with costly deep specialization is now fully turnkey.

What has become easier is becoming differentiated. Today’s successful hosting companies are more differentiated from their competitors by their focus, rather than their technology. A hosting company with a differentiated focus in a niche market is more likely to be succeed. Sustainable hosting does not require thousands of patrons, it just needs a healthy recurring revenue stream and aligned customers.

The Missing Piece: Discovery on the Open Web

His views on WordPress are informed by this same philosophy. When asked what WordPress still struggles to solve, he pointed to discovery rather than performance or interface design. WordPress gives you the tools to take ownership and independence, but provides very few built-in ways for you to reach new audiences.

“I don’t think we’ve fully cracked the problem of discovery for WordPress creators yet.”

Social platforms succeed because they own distribution. Independent sites rely on search, newsletters, and manual promotion, which can be increasingly difficult as AI-generated content floods the web. Grierson believes the opportunity lies in creating an opt-in discovery layer that helps readers find creators without sacrificing WordPress’s open nature.

Scaling Without Losing the Open Web

Seen through that lens, global expansion is not just about geography. It is about scale without centralization, growth without enclosure, and helping people connect across borders while maintaining ownership of their work.

If Automattic can pair true international expansion with better discovery for independent creators, the next chapter of WordPress may help define a more open, more human internet, one that grows globally without becoming another walled garden.