TLDR: Artificial intelligence is transforming how businesses operate, but it does not replace the need for trust, strategy, and human connection. In this interview, Kevin MacGillivray shares why businesses need strong systems before using AI, why websites matter more than ever, and why authenticity remains a major advantage in an increasingly automated world.
Introduce the Series
Welcome to Wodobo’s thought leadership interview series, where we sit down with innovators, business leaders, and industry experts shaping the future of digital business. In this series, we explore the trends transforming how companies grow, connect, and compete in an evolving online world.
For this feature, we spoke with Kevin MacGillivray, CMO at Pressable, an Automattic company focused on WordPress infrastructure, about one of today’s most talked-about topics: artificial intelligence and the role human connection still plays in business success.
Meet Kevin MacGillivray
Kevin MacGillivray is the Chief Marketing Officer at Pressable, where he leads growth, go-to-market strategy, and AI initiatives across WordPress infrastructure. Pressable is part of Automattic, the company behind WordPress.com and other products that help power the web at scale.
Before joining Pressable, Kevin spent more than five years at Shopify, where he helped drive GTM and commercialization strategy across product launches, pricing evolution, and international expansion. His career also includes leadership roles at TELUS and other high-growth environments, giving him a broad view of how brands grow, communicate, and adapt across different stages of business.
That combination of SaaS, commerce, platform, and marketing leadership gives Kevin a perspective that is especially relevant right now. He understands how AI is changing workflows, how WordPress infrastructure supports modern businesses, and why human judgment still matters when technology accelerates everything else.
About Pressable
Pressable is a managed WordPress hosting company built for performance, reliability, and scalability. As part of Automattic, Pressable supports businesses, agencies, and WordPress professionals who need hosting that can keep up with modern demands.
Kevin’s role at Pressable sits at the intersection of growth, marketing, product strategy, and AI. That matters because the hosting layer is no longer just about uptime and speed. It is also about how businesses manage complexity, support scale, and connect their systems to the tools they actually use every day.
In Kevin’s view, the future of WordPress infrastructure is becoming more conversational, more efficient, and more connected to the way real teams work. That makes his perspective especially useful for business owners trying to understand where websites, AI, and growth are headed next.
Article Summary
Artificial intelligence is rapidly changing how businesses operate. From automation to customer support to marketing systems, AI is creating new opportunities for efficiency and growth.
However, during our conversation with Kevin, one message stood out clearly: technology should enhance human connection, not replace it.
Kevin shared valuable insights on why businesses need strong systems before implementing AI, why websites are becoming more important as AI search grows, and why authenticity remains one of the strongest competitive advantages in today’s market.
His perspective offers a practical and hopeful reminder that while tools evolve, trust, relationships, and human insight still drive business success.
Who We Are Seeking
At Wodobo, we seek voices who bring clarity to emerging trends and can help business owners confidently navigate change.
We look for experts who combine real-world experience with forward-thinking insight, especially those helping businesses understand how digital infrastructure, strategy, and technology work together.
Leaders like Kevin help bridge the gap between innovation and practical business application.
Why We Sought Him
With AI dominating conversations across every industry, many business owners are asking important questions:
- Will AI replace jobs?
- Do websites still matter?
- How should businesses prepare?
- What role does authenticity play in an automated world?
We wanted perspective from someone who understands both technology and business implementation. Kevin’s background in growth marketing, WordPress infrastructure, and commerce made him an ideal person to help answer those questions.
Why He Was a Perfect Interviewee
Kevin brings a balanced perspective that many businesses need right now.
He understands the technical side of AI, automation, hosting, and digital ecosystems, but he also recognizes the importance of human behavior, trust, and communication.
Rather than speaking in hype or fear, Kevin offered practical advice rooted in real business needs. His ability to explain complex shifts in a grounded and accessible way made him the perfect interviewee for this conversation.
Main Information in Q&A Format
Q: You recently gave a keynote about the importance of connection and context as AI reshapes our industry. What was the moment or realization that made you feel like that message needed to be said out loud?
Kevin: Businesses are moving quickly toward AI, but many people are forgetting that tools only work well when they are guided by human understanding. Connection, collaboration, and context are what make technology useful.
Q: What were people’s reactions when you shared that connection still matters when it comes to AI?
Kevin: Many people felt encouraged. There is a lot of fear that AI will replace jobs or remove the need for people, but the reality is that human input is still essential. AI can support work, but people create strategy, relationships, and trust.
Q: Many people say AI is just a tool, but businesses are not always sure how to use it that way. How do you explain that?
Kevin: AI works best when businesses already have systems, structure, and goals in place. If processes are disorganized, AI only amplifies that confusion. When the foundation is strong, AI can simplify and automate repetitive work.
Q: A lot of people are asking whether websites even matter anymore in an AI-driven world. How do you think about the role of a website today compared to two years ago?
Kevin: Websites matter more now because they are the source of truth for a business. AI gathers information from many places online, and not all of it is accurate. A clear, updated website helps define who you are and what you do.
Q: What would you say signals authenticity online today?
Kevin: People are becoming better at recognizing content that feels overly automated. Businesses that combine technology with real voice, real insight, and genuine expertise will stand out much more than those relying only on generated content.
Q: What are clients asking now compared to a year ago?
Kevin: Clients are asking broader questions. They want to know how AI interacts with their websites, how their information is represented online, and how they can prepare their digital presence for the future.
Q: If you could sit down with every small business right now and tell them one thing about what is coming and how to prepare, what would it be?
Kevin: Build strong systems first. Organize your processes, understand your operations, and know your customer journey. Once that foundation exists, AI can become incredibly valuable.
Q: What final perspective would you leave business owners with?
Kevin: Every major technological shift creates fear at first. We saw it with the internet, computers, and smartphones. AI is another evolution. Businesses that succeed will be the ones that adapt while continuing to prioritize people.
Closing Thought
Technology will continue to evolve, but the core of business remains the same.
People still choose to work with people they trust.
