How Curiosity Turned into a Career in Email — Anna Levitin

“Can you also send emails?” One small question, one extra task — and suddenly you discover a field that just clicks.

That’s what happened to Anna Levitin about nine years ago. What began as a casual request at a startup quickly turned into something much bigger. Email gave her the perfect space to combine pattern recognition, creativity, data, and collaboration — and she’s been shaping lifecycle marketing ever since.

In this conversation, Anna shares how she thinks about the different sides of email work, why she balances a full-time role with freelance projects, and why the email community continues to play such a big role in her growth.

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What brought you into email in the first place, and how has your role evolved since then?

About nine years ago, while working in marketing at a startup, I was casually asked, “Can you also send emails?” I had never done email marketing before, but I gave it a try and quickly realized that segmentation and audience building were exactly what I loved. It clicked with my academic background in cultural typology, where we analyze, classify, and understand communities. Email marketing became a natural extension of that work, just powered by data instead of theory.

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Which positions have shaped your skills up to now?

Every role I’ve had has shaped my skills. I see email and lifecycle marketing as a mix of four parts: analytical (data and insights), creative (ideas and concepts), operational (QA, HTML, execution), and communication, working closely with product, sales, and data teams. Often, even a casual conversation can spark the next great flow.

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What drives you to balance both a steady role and freelance work? What does each give you — and what does each take away?

Full-time roles let me go deep, owning one product, working closely with the same teams, and building long-term impact. Freelancing, on the other hand, gives me exposure to different brands, tools, and challenges. Together, it’s a win-win: depth on one side and constant learning on the other.

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How do you stay sharp and continue growing your expertise with competing demands?

I grow by staying close to two things: the email community and hands-on work. The email community is incredibly strong, people openly share, support, and learn from each other. And staying hands-on, making real decisions and facing real challenges, is what truly keeps me up to date.

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If you imagine your ideal setup, would you keep the mix — or choose one path fully? Why?

Ideally, I’d keep a mix. I want to dedicate at least 50% of my time to one product, going deep and creating long-term impact, while using the rest for selected freelance projects and education, teaching, webinars, and courses. Sharing knowledge and helping people enter the field has always been an important part of my work.

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What We Keep Learning From Email Career Paths

Anna’s story highlights something we keep seeing across the Email Freelancer Pathways Project: very few people plan a career in email. Most of us arrive through curiosity, opportunity, or a moment where someone simply asked, “Can you do this too?”

What stands out in Anna’s path is the balance she’s built between depth and exploration. A full-time role allows her to deeply understand a product and build long-term lifecycle strategy, while freelance work keeps her exposed to new tools, brands, and ideas. At the same time, she stays connected to the email community and actively shares knowledge through teaching and education—helping others find their own entry point into the field. 

That combination—community, hands-on work, and knowledge sharing—is something many people in this industry relate to. Email isn’t just a channel; it’s a craft that grows stronger when people learn from each other. 

And that’s exactly why this project exists: to document the many different ways people find their way into email, build their expertise, and shape careers that often didn’t exist when they started. 

Anna’s pathway is a reminder that sometimes the most meaningful careers begin with a small opportunity—and the curiosity to say yes.

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Add Your Voice!

This interview is part of The Email Freelancer Pathways Project, a series documenting the many different paths into email.

Through a short survey, I’m collecting experiences from email professionals to make these career journeys visible — and to help advocate for better access to the tools people are expected to master.

If you work in email in any capacity, your experience matters.

👉 Take the survey here!

📩 Connect with me on LinkedIn or send a message.

With Love from Canada
Annett
Founder, EmailBoutique.io

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