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September 17, 2025 - Articles

Email Peeps 70: Will Pearson

How did you get into lifecycle marketing? 

My entry into lifecycle marketing, like many others, was somewhat accidental. While working at Vivino, the wine app, I was responsible for e-commerce operations, including inventory management and sales forecasting. During that time, we discovered that email was by far the most effective revenue channel. At one point, it was driving more than 50 percent of revenue. That experience gave me an unexpected but invaluable introduction to the power of lifecycle marketing.

My now co-founder at Scalero, Brant Cebulla, was one of the first marketing hires at Vivino and led the lifecycle team there. We worked closely together to develop strategies, implement technologies, and refine processes that shaped Vivino’s lifecycle marketing approach. At Vivino, I gained a high-level perspective on the discipline. Later, when we launched Scalero, I deepened my expertise by learning the technical details and operational nuances that drive effective lifecycle marketing.


What are some quick wins that lifecycle marketers could implement today?

As lifecycle marketers, our instinct is often to segment lists as much as possible and personalize at an extremely high level. My advice is not to overthink that process. The most effective way to drive strong performance from an email is simply to create a great email, feature a strong product, and present a compelling offer. If those fundamentals are in place, the email will perform well regardless of how the segments are structured. Instead of investing too much energy in overly complex segmentation and personalization, focus on the quality of the content and the value of the products you are promoting.


How are you using AI at Scalero?

We are using AI in a number of ways at Scalero. First, every team member has access to ChatGPT Pro, and they have the freedom to use it in whatever way is most helpful. This has proven valuable for a range of tasks, including troubleshooting email code, translating messages into more formal English, and serving as a creative thought partner to be strategic with clients.

Second, many of the tools we use on behalf of our clients, including some of the top ESPs on the market, are now implementing AI features. We are exploring where those capabilities can be most beneficial, whether by streamlining the process of building segments and flows or by saving time on routine tasks. This allows us to dedicate more energy to the strategic and creative work that drives results for our customers.

Finally, we have developed a number of internal automations that accelerate workflow. For example, when a client sends us a Slack message, we can instantly convert that message into a Notion ticket by reacting with an emoji. The ticket is then automatically assigned to the right team member, saving project managers significant time that would otherwise be spent on data entry and task routing.

We know AI is moving very fast and we are working hard to stay ahead of the curve within this industry.


What’s in your toolbox?

Hardware:

  • Not much! I function very lightly. I can get all of my work done on a MacBook. I have a monitor for enhanced productivity and I wear AirPods on calls. That’s about it.

Software:

  • Gmail
  • Slack
  • Notion
  • ChatGPT
  • Figma
  • Lots of ESPs 🙂

Honestly, there are a dozen more I am trying at the moment. Some stick, some don’t.


What are some of your favorite trends in email design and content?

There is no one better to answer this Scalero’s Principal Visual Designer, Alan Alarcón! Here is his response:

“I’m always attracted to email designs that are both functional and expressive, something that not only fulfills a purpose but also reflects the brand’s identity, emotion, and culture.

One trend I really like is maximalist design: bold titles, large images, vibrant colors, carefully curated to be eye-catching and accessible. It’s an effective way to grab attention while still feeling polished.

Another favorite is the editorial-style layout. These emails resemble reading a magazine, with strong typography, clear hierarchy, and layouts where the text seems to speak directly to you. They create a rhythm and narrative that make the experience more immersive.

I also enjoy rounded box outlines. They help define space in a clean, friendly way and allow for creative play with shape, spacing, and visual balance.

Then there are unconventional holiday campaigns, emails that invent new holidays, celebrate unexpected moments, or incorporate humor into seasonal messages. They’re fresh, original, and great for showcasing brand personality.

Finally, I’m really into altered or surreal designs, with textures, layered colors, and unusual shapes that break from convention and feel artistic. These stand out when done intentionally.”

Overall, what excites me most is the freedom to experiment, not feeling restricted by format. The best emails today push creative boundaries while staying purposeful and true to the brand.


What’s your favorite email campaign of all time? Why?

My favorite email campaign of all time, which I will admit comes with some bias, is from my days at Vivino. Vivino is an app that allows users to take photos of wine bottles in order to learn more about them, rate them, and order them. One of our most innovative campaigns leveraged those user-generated images directly within email.

The use case was simple but powerful. A user might be drinking a wine on a Friday evening, take a picture of it in the app, and submit a rating. The very next day, we could send that user an email in which the hero image was the photo they had taken themselves. The message would say something like, “We hope you enjoyed your wine last night. It was a Pinot Noir from Sonoma. We actually have a Pinot Noir from Sonoma available that is rated higher and is offered at a lower price than the one you purchased.”

This campaign represented the kind of personalization that every brand strives to achieve. It was essentially a one-to-one message, built around the user’s own behavior and even their own photo. 


What’s your advice for new marketers entering the industry in the next few years?

For new marketers entering the lifecycle space, remember that success comes from balancing both art and science. Data is essential, but it is not everything. Sometimes the best results come from creative risks, whether that means experimenting with unexpected segments or mixing polished design with plain text emails. Use data to learn and refine, but do not let it limit your creativity.

It is equally important to make sure the rest of the company understands the impact of lifecycle marketing. Email is often the highest ROI channel, and marketers should highlight that value, connect it to broader business priorities, and take initiative rather than simply responding to requests. Lifecycle can make a huge difference within an organization.

Much love,
Andy

Email: [email protected]
Twitter: @emaillove