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The Journey of a Second-Generation Email Marketer: Reflections on Evolution and Innovation

What inspired me to enter the field of email marketing, and how did my career evolve over time?

My journey into email marketing started early, thanks to a unique blend of family influence and personal interest. My mother was already working in the industry, so I had exposure to email marketing from a young age. I’d always been interested in computers and graphic design, so naturally, I began teaching myself HTML specifically for email back in the early 2000s. Even as a high school student, I took on campaign management tasks in my mother’s home office, where she ran an ESP called Ezemail in Australia.

After finishing university, I found myself returning to email marketing full-time and eventually joined Holistic Email Marketing with Kath Pay, who had been consulting independently for years with her company, Plan 2 Engage. This journey has given me a unique and hands-on perspective on email marketing, from its foundational techniques to today’s evolving strategies.

What unique perspective does being a second-generation email marketer bring to my work?

Claiming the title of a second-generation email marketer is certainly unique—it’s not often you see generational vocations emerging in new fields like digital marketing. Being part of this “lineage” gives me a perspective on email’s evolution that few others have. Working alongside Kath, one of the leading minds in email marketing, has shown me what it takes to become a thought leader in this industry. I’ve watched her dedication and seen the hurdles she’s overcome to make her mark. This background instills in me a deep respect for the discipline and a drive to contribute with the same integrity and commitment.

How have I seen email marketing evolve, and what excites me most about its future?

I’ve been in email marketing long enough to remember the early days of “batch-and-blast” campaigns. Campaign management was one of my first tasks around 2000 or 2001, and back then, email was all about the basics—getting a message out to as many inboxes as possible. While email marketing has come a long way since then, it’s interesting to note how much of the core functionality has stayed the same. This consistency is both a blessing and a curse: while new technologies have introduced flashier features and more personalised options, the foundational mechanics of email marketing haven’t drastically changed in over two decades.

What excites me now is the growing role of AI and predictive analytics, which allow us to fine-tune our strategies in ways that weren’t possible before. These tools bring a new layer of sophistication to email marketing, enabling us to go beyond just opens and clicks to understand and predict what will resonate with our audiences. The challenge—and the thrill—lies in balancing these technological advances with tried-and-true methods that have proven their value over the years.


This post is just the beginning of a series where I’ll be diving deeper into the journey, insights, and philosophies that shape my approach to email marketing. As with any field, there’s so much to unpack—from the strategies that drive results to the evolving challenges we face.

Jonathan Pay's avatar

By Jonathan Pay

With over 18 years of experience in email marketing, Jonathan is the world’s first second-generation email marketer. Having worked for service providers, agencies, and brands, he brings along an understanding of code, design, and strategy with a focus on excellent customer experiences.

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