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How did you get into AI?

It was basically a meet-cute — me and AI. I was in my first year of grad school, pursuing a PhD in Computer Science with a focus on cybersecurity. Part of our program required us to attend research talks to explore other areas of study.

One day, I ended up at a presentation where someone was using early Natural Language Processing (NLP) models to analyze New York Times articles. This was still the early days in the field, and the models and the results were rough — like really bad. After the talk, I did something totally out of character and told the presenter it didn’t land for me. What I expected to be a brief (and probably awkward) exchange turned into a real conversation — and somewhere in the middle of it, something shifted. I walked away from that moment with almost an overwhelming sense of clarity: This was what I was going to do with my life. Not cybersecurity. Not something adjacent. AI.

That one unexpected encounter completely changed my trajectory. It led me to build a startup (later acquired by Grubhub), manage data science teams for companies (like TaskRabbit and Bluevine), and eventually step into a new role at Constant Contact, serving as the first Director of AI. Today, I get to guide the development of AI tools that help small businesses and nonprofits create smarter content, personalize their messaging, and run more effective campaigns. And it all started with one rough demo, one honest comment, and one unexpected spark with AI.

How do you see AI impacting the role of email marketers in the next five years?

AI is already reshaping what it means to be a marketer, shifting the role from campaign builders to AI-powered strategists.

Right now, things are changing quickly. Tasks like writing subject lines, picking send times, and segmenting lists are being automated, freeing marketers to focus on strategy and creativity. They’re blending this creativity with data-driven decisions that drive results, not based on guesswork, but on real insights. But more importantly, AI is helping create smarter, more personalized experiences that actually connect with people in real time.

The shift couldn’t have come at a better time, especially for small business owners. They didn’t launch their business to become full-time marketers, and most don’t have hours a day to dedicate to campaigns. When AI tools are integrated thoughtfully — to make work faster, easier, and more effective — it’s a total game changer. And, we’re seeing this new mindset start to take hold. Our recent Small Business Now study found that 92% of new entrepreneurs see technology as essential to growth, and 72% plan to use AI for marketing this year. That’s huge.

Just a few years ago, AI felt slightly out of reach for most, but now, it’s part of everyday lives and workflows. Still, there’s room for growth. While many say they’re using AI, far fewer are doing so meaningfully. A lot of teams are still in the “bring your own AI” phase, experimenting on the side without fully integrating AI into how they work. That’s where early adopters play a key role: helping teams build confidence and creating a culture where AI isn’t just available, but fully embraced. As marketing increasingly becomes more about optimization, those who know how to team up with AI will be the ones who thrive.

How should email marketers be using AI today?

To put it simply, AI is a game-changer for marketing, especially for small businesses, and it’s helping remove the guesswork and the grind from the day-to-day. Start with the basics — use AI to draft subject lines with a higher likelihood of getting opened, generate content ideas when you’re stuck, and optimize send times for higher engagement rates. Those previously time-consuming tasks can now be done in seconds, giving you more space, time, and energy to focus on strategy and storytelling.

The real superpower of AI, though, is personalization. With the right tools, you can use customer data (e.g., what people click or ignore, how they behave, etc.) to segment your lists and tailor your messaging in a way that feels 1:1, even at scale. This hyper-relevance was once a luxury, but today, it’s a necessity — and AI makes it possible without needing a huge marketing team or budget.

Plus, AI tools are getting more intuitive and accessible, so you don’t even need to be a tech expert to get started. It’s about helping people work smarter, not harder, because marketing should fuel your growth, not drain your time. So, for all the email marketers out there wondering where to begin with AI, my advice is simple: Start small, stay curious, and let the tools do the heavy lifting. Your customers will feel the difference, and so will you.

What’s in your toolbox?

At Constant Contact, we’re a Google Workspace shop, and what’s great about that is a lot of my go-to tools already live right in that ecosystem. Two of the AI tools I personally rely on most are Gemini and Notebook LM — they’ve become a core part of how I research, learn, and share information.

Of course, everyone has their own favorite tools and their own way of integrating AI into their workflows, but here’s an example of mine: First, I set the foundation by taking the time initially to craft clear and precise prompts. I like to start with Gemini’s Deep Research model (2.5 Pro). I put a lot of intention into the prompt engineering up front. The more precise and granular I can get, the better the output. Once Gemini generates the report, I export it straight to my Google Drive. From there, I’ll import it into NotebookLM, which is perfect for making sense of all that information. I can ask specific questions, explore angles I didn’t think of initially, and even turn the content into something I can listen to — like a podcast I can queue up for my commute home.

It’s like having an AI-powered research assistant that doesn’t just find answers, but helps connect the dots. So, whether I’m digging into trends, prepping for a presentation, or trying to distill complex research into something actionable, this workflow gives me the depth and flexibility I need to turn passive time into active time, stay sharp, and work more efficiently.

What’s your WFH setup?

I’m pretty serious about my work-from-home setup. It’s got to support focus and creativity, so I try to keep it functional and inspiring. I have an adjustable standing desk for long work sessions, two external monitors for juggling research, dashboards, and communications, and my MacBook Pro on a stand for organization and ergonomics. Behind me, there’s a bookshelf packed with favorites, with everything from tech and AI to business strategy and a few curveballs for fun. It hasn’t quite made it to the bookshelf yet, but I’m currently reading “Build a Large Language Model (From Scratch),” learning more about creating LLMs. Then, there’s my vinyl record player — the not-so-secret asset that drives my productivity. I have a pretty solid collection, and when I’m deep in coding or heads-down on strategy, putting on the right record really helps me get in the zone.

But, the best addition has to be my Corgi, Franki, and Westie, Gigi. They’re my unofficial furry coworkers that are excellent for mid-day walks or when I need to bounce an idea off someone who won’t interrupt. It’s a setup that keeps me productive, focused, and grounded, with just the right amount of fun and creativity mixed in.

Are you using AI at Constant Contact? How?

Definitely — AI is a huge part of what we’re building at Constant Contact, and I’m also using it firsthand through my consulting side hustle, too.

At Constant Contact, our goal is to make AI seamless for small businesses. Our AI-powered marketing tools, like Campaign Builder and BrandKit, help small businesses and nonprofits achieve better marketing results without needing to be expert marketers. Campaign Builder automates the areas where many get stuck—content creation, channel selection, and scheduling—turning marketing goals into fully executed,
multi-channel campaigns in minutes. BrandKit makes sure it’s all on-brand, automatically pulling in your brand colors, logos, fonts, and more, straight from your website. Plus, our AI Content Generator helps save time, spark new ideas, and write copy that resonates. We also have AI working behind the scenes with features like Spaminator, our AI-powered spam-detection system, which helps our customers maintain high delivery rates while ensuring emails remain safe, secure, and effective.

Personally, I use these same tools for my own marketing for my consulting business, unexplainable.ai — helping me create multichannel campaigns that sound like me and connect with my clients — even when I’m short on time. I’m not a designer or a copywriter, but thanks to AI, I don’t have to be.

We’ve designed these tools with real SMB challenges in mind, and AI helps solve these. Whether it’s crafting a message that hits the mark, choosing the right send time, or understanding customer behavior to drive personalization, AI helps small businesses market smarter, not harder.

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

The CGI Rochester International Jazz Festival is a perfect example of how thoughtful email marketing can fuel both community engagement and operational efficiency. This isn’t just a music festival—it’s a nine-day event that brings 1,750 artists from 14 countries to perform in over 300 shows. And the scale of the event demands seamless communication across a wide range of audiences: attendees, sponsors, press, and staff.

What stands out is how effectively the team manages complexity without compromising clarity, using Constant Contact not just as a tool but rather as a central hub for consistent, targeted communication. They’ve nailed segmentation, building lists for each of their audiences for more relevant and timely messages leading up to the event. Their major lineup announcement in March is a masterclass in coordination, with pre-scheduled sends that reach inboxes exactly when needed. They also lean heavily on reporting: tracking engagement and refining future sends based on what resonates.

From collecting RSVPs for private sponsor events to driving foot traffic to local businesses during the festival, every email has a purpose. And the results back it up: higher open rates, consistent year-over-year list growth, and most importantly, a stronger connection with the Rochester community. It’s proof that when email marketing is done right—with the right tools—it’s more than a campaign. It’s the heartbeat of an event that’s generated nearly $200 million for the local economy.

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

My advice: Stay curious, start small, and go in with an open mind, especially when it comes to AI. Adaptability isn’t just how you survive in this industry — it’s how you grow. So don’t let these tools intimidate you. AI might be changing marketing fast, especially for small businesses, but it’s also making things simpler. Our AI tools are taking complex tasks like campaign planning, content creation, and personalization, and making them accessible, even if you don’t have a marketing background. If you’re just starting out, find one area that slows you down — maybe writing subject lines or building social content — and try using AI to help. Set a goal (like “cut email drafting time in half”), track your progress, and iterate. It’s all about experimenting and finding what works. And, for business leaders:

Don’t ignore AI. Your team will use it with or without you, and it’s better to guide that adoption than scramble to catch up. The goal is to empower your people to be more efficient without introducing unnecessary risk.

Ultimately, think of AI as your assistant, not a replacement. Let it handle the repetitive stuff so you can focus on the creative and strategic work that really drives results. That mindset will take you far.

Much love,
Andy

Email: [email protected]
Twitter: @emaillove