5 Tips to Win Your Readers Back with Re-engagement Emails

Hi! In case we haven’t met before, I’m Justine Jordan, the Head of Strategy and Community here at Beefree. Over the past 16 years, I’ve worn many hats: designer, developer, marketer, community builder, and even the occasional cat GIF curator. I’ve been fortunate to build a career based on deep expertise in all things inbox, where I’ve seen firsthand the incredible potential of using email to connect people and businesses.

Way back in 2007, I fell into the email industry almost by accident. Fresh out of college, I started my career as a designer focused on creating print and brand assets. Frustrated by what felt like a lack of impact and respect in my design role, I wanted to be seen as someone who could help drive business success. Unlike brochures, email design offered instant feedback—opens, clicks, and conversions could tell a story.

I was hooked. And as the industry grew, so did my appreciation for email's ability to forge direct connections with people, right in their inboxes.

And yet, we all know that 16 years in any field (especially email!) is a long time. Email today is vastly different from the scrappy marketing channel I stumbled upon in 2007—even though its core mission remains the same: building meaningful, personal connections that drive business results. So, let’s dive into the fascinating, often underappreciated evolution of email and explore why it remains as relevant and impactful as ever.

A decade of opportunities and challenges

Personalization and the journey to hyper-relevance

When I started, email was largely one-size-fits-all. Campaigns were often “spray and pray” or involved very simple or binary yes/no personalization. 

Today, personalization has evolved beyond first names in subject lines to sophisticated, data-driven approaches. Marketing teams can now leverage insights from browsing behavior, purchase history, and even real-time data, adapting dynamically to each recipient’s preferences and past interactions. This technology is still advancing rapidly—it’s hard to believe that it was barely possible two decades ago. 

Rendering issues

In the past, we’d spend hours making sure emails looked as good in Outlook as they did in Gmail—and, going further back, in Lotus Notes! The visual building tools in most ESPs were buggy and produced bloated HTML that was ready for the web, but didn’t meet the unique constraints of email.

Fast forward to today, and while rendering challenges haven’t disappeared entirely, they’re far less consuming. Gmail's support for embedded CSS was a game changer, signaling an era where our designs could focus more on creativity and less on workarounds.

Rendering tools made this process easier, and drag-and-drop editors like Beefree produce clean, email-friendly HTML. What once required hours of coding and testing now takes minutes, freeing email marketers to focus on crafting their messages instead of debugging their code​​. 

Mobile-first and responsive design

Mobile-optimized email design used to be a “nice to have,” but today, it's essential. 

Brands must deliver a seamless experience across a wide range of devices and subscriber preferences​. This shift required us to think beyond just fitting content on smaller screens; it required a rethinking of layout, typography, and hierarchy. Today, it's about more than just looking good on mobile—it's about providing immediate, relevant, and accessible information.

Interactive and accessible emails

Today’s email campaigns go beyond static images and blocks of text. Interactivity, whether through embedded videos, polls, or even checkout functionality within the email, is changing the game. We’re offering richer experiences that invite users to engage directly within their inboxes​. 

At the same time, accessibility has become a critical consideration. Making sure that everyone can receive and understand your message, regardless of any disabilities or assistive devices they may be using isn’t just good practice, it's an industry standard.

Privacy, authentication, and the role of trust

Over the past decade, privacy regulations like GDPR and CCPA along with authentication requirements from major receivers like Gmail and Yahoo have reshaped how people view the inbox and their relationship with brands that send email. 

While the introduction of these new regulations initially posed considerable questions, confusion, and challenges, they also served as a valuable reminder that great marketing starts with trust, transparency, and consent. This shift encouraged brands to communicate with audiences in a more transparent, respectful way, reinforcing the idea that consumers own their data.

Email’s place in the C-Suite

Email marketing has always had champions, though convincing executives of its strategic value hasn’t always been easy. Over time, email advocates—often the Email Geeks among us—have successfully positioned email not as a tool for increased revenue but as a trusted channel for delivering essential information and building long-term relationships​. Today, email is often recognized as a valuable asset in C-suite conversations about customer experience, retention, and ROI.

The power of community

The email industry has grown from a niche group into a thriving community that shares, supports, and learns from one another. I’ve had the privilege of being part of a community that openly shares best practices and fosters innovation. 

Events like Unspam, Email Camp, and Litmus Live highlight just how much email professionals have pushed boundaries over the past decade​. This spirit of collaboration keeps the industry strong and forward-looking.

My #1 Lesson: Put People First

If there’s one lesson I’ve learned, it’s this: email should serve the audience, not just the business. 

Reaching people in their inbox is a privilege, not a right. Too many brands treat email like an ATM, pumping out sales and promotions without considering the impact on loyalty, retention, or the user experience. Yet the companies that treated their emails as conversations rather than megaphones? They’re the ones that thrived.

Email is unique because it arrives in a personal space (the inbox) where people are expecting personal messages and relevance. It’s an honor to land in someone’s inbox, so the content should meet that privilege with empathy and value. 

Some of my favorite brands—like Going—understand this: they craft emails that feel like they are speaking directly to me—thoughtful, helpful, and human​​. That’s the level of care that builds trust and loyalty. 

Advice for the future: Embrace empathy and experiment

Reflecting on the past decade in email marketing feels like watching an old friend evolve. I've seen firsthand how a channel that is frequently sidelined and declared “dead” has become a pivotal player helping businesses grow and connect with their audience. 

With each email renaissance comes new trends, innovations, preferences, and technology. 

Every few years, email redefines its role in our lives as marketers, business leaders, and as humans. Email's journey has been one of resilience, adapting to new trends, regulations, and consumer expectations while remaining at the heart of customer engagement. 

For anyone starting off in email, my biggest advice is always keep your audience at the heart of your campaigns. Email marketing is both art and science, and finding that balance is what makes this industry so rewarding. 

Don’t be afraid to test your ideas—measure, refine, and get creative with how you deliver value. But always remember, the inbox is personal territory. If you respect that space, you’ll have a powerful, lasting connection with your audience.

I’d also suggest building a solid understanding of the complexity behind email—learn the basics of deliverability, the role of email in multi-channel lifecycle and marketing campaigns, connecting data and APIs, multivariate testing, and stay current with the latest tools and platforms. 

With AI, privacy regulations, and rising consumer expectations, we’re bound to see even more shifts in how we approach email. Knowing how these elements work under the hood will only make you a more effective, innovative marketer. 

But one thing remains: the need to make email human-centric. This will mean staying adaptable and continuing to create value-driven content that aligns with the subscriber's needs. Far from dead, the real magic of email is the central role it plays in our lives—and it’s not going anywhere. Here’s to another decade of email evolution 🙌

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As we continue to celebrate Beefree’s 10-year journey of innovation and creativity, we’re thrilled to mark this milestone with the launch of The Beefree Academy.

Over the past decade, Beefree has been dedicated to empowering users with intuitive tools that make email design faster, smarter, and more impactful. Now, with the launch of our Academy and certification program, we’re taking our mission one step further by helping users build their expertise in email design and creation.

The inspiration behind the Beefree Academy 

When we envisioned Beefree Academy, we knew it had to be more than a series of product tutorials; it needed to be a resource that you could benefit from at every stage of your journey. 

The Beefree Academy is designed to inspire confidence, foster success, and provide ongoing support as you grow, enabling you and your team to get the most out of our platform – here’s how: 

Smooth and speedy onboarding:

Starting with a new platform can often be overwhelming and the time spent during onboarding is valuable. The Academy fast-tracks the learning process, offering structured, bite-sized lessons suitable for people of varying skill sets, from beginners to seasoned designers. Each lesson is designed to help you get comfortable with Beefree’s tools, so you can dive into projects quickly and with ease.

Explore new possibilities: 

Many users only scratch the surface of Beefree’s capabilities—we aim to change that. The Beefree Academy allows you to familiarize yourself with advanced features you might have been wary of before.

As you and your team grow from casual users to power users, you can gain more control over your email design, find new ways to optimize your workflows, and strengthen the impact of your campaigns. 

Troubleshoot like a pro:

Technical support is most effective when you have tried-and-true resources to solve challenges independently and on your own schedule. With Beefree Academy, you and your team can confidently troubleshoot independently by accessing targeted, step-by-step solutions whenever you need them. 

Advance your email marketing expertise: 

Beyond learning the platform, the Beefree Academy provides a comprehensive learning experience with valuable tips and best practices for email design and marketing. Soon, our lessons will extend far beyond the basics, guiding you through the process of creating visually compelling, high-converting email layouts while ensuring your designs follow proven best practices. 

You and your team will gain insights into crafting effective email marketing strategies that resonate with your audience, along with the skills to harness the power of AI in your campaigns. Additionally, we’ll explore the latest trends shaping the future of email design, empowering you to stay ahead of the curve and continually enhance your campaigns

What’s inside The Beefree Academy: 

Beefree Academy is thoughtfully designed to cater to users at all levels—from beginners just starting their email design journey to experienced designers looking to formalize their expertise in email design.

Courses:

The courses in Beefree Academy help users deepen their knowledge and understanding of the key tools and features within Beefree. As you complete courses, you’ll have the chance to demonstrate your skills through assessments and earn certifications that showcase your proficiency within the platform. To kick things off we have launched two courses: 

1. Beefree 101: If you’re new to Beefree this course is the ideal starting point. We’ll walk you through the basic functions and features through step-by-step guides. Certified team members can then train colleagues, creating a ripple effect of improved productivity and design standards throughout the organization.

2. HubSpot x Beefree: This course is perfect for HubSpot users looking to supercharge and streamline their email marketing with Beefree. Through this course and certification, you and your team can learn how to design personalized, mobile-optimized, and engaging campaigns in Beefree for HubSpot. 

For organizations, having team members become Beefree certified can standardize email design processes across the company ensuring that all campaigns are consistent in quality and adherence to email design best practices. 

Tutorials and walkthroughs: 

Our comprehensive tutorials and walkthroughs are designed to help zero in on a particular aspect of Beefree and email design. These step-by-step guides are perfect for users who prefer a hands-on approach to learning. 

By providing these instructional resources, we aim to eliminate confusion or uncertainty, allowing you and your team to realize value from the start and adopt Beefree with confidence.

Enroll now – it’s free! 

The Beefree Academy certification is designed to fit seamlessly into the busy lives of busy professionals, allowing you to learn at your own pace and enhance your skills on a schedule that works for you. Whether you’re aiming to elevate your current expertise or start a new journey in email design, Beefree Academy offers flexible, high-value learning that you can access anytime, anywhere – completely free.

Ready to take your email design skills to the next level? Enroll in the Beefree Academy today and start building the expertise that will set you apart! 

Through my years in the tech industry, there have been few innovations that have generated as much excitement – and anxiety – as generative AI (GenAI). While AI has changed how I work and create for the better, I will admit that it also came with a period of fear and pushback. I have seen the way new technologies come and go and are quickly forgotten. And, the headlines painting GenAI as a “job-stealing superpower poised to replace us all” did not make me feel any better. 

The turning point for me came on a random weekday when I turned to my now good pal, ChatGPT, to help me write a brief for a blog. It took some back-and-forth, but the final result turned out to be something I was really proud of. Since then, the integration of GenAI into my workflows has been slow, but intentional. 

While I do still believe there are legitimate concerns to have about AI, and not all anxiety is unfounded, some of it is based on fear-mongering. I don’t necessarily believe that we should lean into the dystopian “AI takeover” tropes. While captivating, these arguments often overlook the ways that GenAI can help us to be more imaginative, free us up to do more, and spark creative problem-solving. 

I don’t plan to convince you to use AI (not today at least), but I do hope that you leave today with some insight on the possibilities of AI.

Addressing your concerns: When is fear warranted?

I haven’t been beating around the bush yet and I won’t start now. There’s no denying that GenAI has the potential to reshape certain jobs and industries. The World Economic Forum (WEF) in their “The Future of Jobs Report 2020,” identifies administrative, clerical, and even content-related roles at higher risk due to their structured and repetitive nature. 

AI excels in pattern recognition, data processing, and performing repetitive tasks, which means that roles where predictability is high, creative input is low, and that have clear instructions can be programmed into an AI system and automated. 

While there’s a plethora of other resources on the “negative” impact of AI on the workforce – I want to challenge us to look a bit beyond. What happens when aspects of our jobs are automated or AI-supported? What does that allow us to do more of? What are the limits of AI?  

The reality: AI has nothing on you

Luckily for us, AI struggles to have an intuitive understanding of nuance. The magic of AI lies in what we do with the information it provides us and AI can’t replicate that.  Our superpower lies in our ability to be creative, our ability to feel, and our very unique human experience.

For example, the brief for this article you are reading was written with help from ChatGPT, and the research to put this together was gathered from Perplexity (verified by me afterward, of course). While these tools were quick to pull facts and suggest ideas, they lack the human experience and emotional intelligence to tell a story about why AI may be scary for folks like you and me—regardless of how much prompting.  

As a content creator, I refuse to see GenAI as a replacement for what I do. Rather, I know that my human experience, when paired with AI’s limitless knowledge, can propel my skills to new heights. 

How folks are using GenAI in their everyday 

The reality (I guess, really, in my opinion) is that GenAI works best when used to complement our expertise. Yeah, it can crunch numbers and even make solid recommendations, but it can’t adapt, empathize, or make strategic decisions when the stakes are high like we can. In these roles, AI may help carry the load, but it’s not steering the ship. 

Here’s how the Beefree team is using AI: 

Marketing Program Manager 

"Sometimes I default to being too straight and to the point when giving feedback on a project, or similar things, so I ask AI for help revising my feedback to be more clear and less “blunt.”

Afterwards, I ask it to explain the types of changes it has made so I can learn and internalize the lessons moving forward to improve on delivering feedback.

AI helps me to be more intentional and empathetic in my communication. I don’t just use it to revise, but also to help teach and aid me in growing as a professional."

- Samantha Hoffmann, Marketing Program Manager

CEO 

"What I use the most these days is AI-assisted search. I very rarely use Google search anymore. My go-to is Perplexity Pro, which I use as an assistant when I need to research topics, figure out best practices to follow in certain situations, and overall try to become better at my job."

‍- Masssimo Arrigoni, CEO

Corporate Communication Specialist 

"I frequently use AI to check my English. For example, I write copy and ask it to verify the accuracy. It often suggests changes, and after some back-and-forth, I work toward creating a polished and more captivating version."

‍- Elisa Battigelli, Corporate Communication Specialist

Head of Product 

"One way I use AI is for brainstorming. I provide as much context as possible—notes, references, and ideas—to help build a detailed outline for a topic. From there, I request multiple iterations, sometimes adding additional context, asking the AI to be wild and creative with it, or challenging the initial output.

This approach doesn’t give me a finished text I can use directly, but it generates a rich set of ideas and points that I can further research."
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- Guille Padilla, Head of Product 

Backend Engineering Associate Manager

"I use AI for my searches and questions on almost every topic, including the more technical around software development."

- Roberto Pomoni, Backend Engineering Associate Manager

Senior Full Stack Developer 

"Aside from brainstorming and summarizing long reads, I use AI on a more technical side to write boilerplate/repetitive code (that always needs to be checked) and manage the time allotment for my working tasks through MotionAi."

- Lica Filice, Senior Full Stack Developer 

Head of People & Culture

"I use AI to help me transform my messy notes more comprehensively to make them easy to share. It also helps me summarize long readings, optimize written communication, get drafts for policy/docs, and get benchmarks and comparisons." 

- Enrica Lipari, Head of People & Culture

What now? Staying relevant and evolving with GenAI

As I said earlier, I’m not here to convince you that AI is right for you, but I will say AI isn’t going anywhere. Instead, it will continue to expand into more areas of work and industries, and its capabilities will only become stronger with time. 

My plan is to lean into this. Dedicate myself to learning and evolving with it. And double down on my expertise. AI makes my job much easier by doing things like helping me write briefs and retrieve data. By letting AI take on my repetitive taks, I gain something even more valuable: time. 

For myself and so many others, this extra time allows us to step away from mundane everyday tasks and spend more time thinking strategically and creatively about the impactful decisions that make a real difference in our work. 

Leaning into AI wasn’t a decision made to stay “relevant” or “head of the curve.” It was about amplifying what makes me and my contributions invaluable. So I ask you: What do you want to do more of? What can you let go of to do this?