What happens when you take your marketing questions directly to the source, live and in person? You get real, unfiltered conversations with small business owners tackling everything from email strategy to AI content creation.

To celebrate National Small Business Week, Dave Charest, Director of Small Business Success at Constant Contact, hit the road for live Q&As at Small Business Expo events in Boston and NYC. In this special “Ask Dave” edition of Be a Marketer, he answers real questions from real business owners on the spot.

In this conversation, you’ll hear insights on how to get started with marketing when you’re new to it, ways to clean up and grow your email list, how introverts can build a content strategy that feels natural, and how to use automation, segmentation, and AI to stay consistent without burning out. Whether you’re running a solo business or building a growing team, you’ll walk away with honest, tactical advice straight from the field.

Additional Resources:

• Getting started with Constant Contact
• Understanding contact segmentation
• Schedule and send an email
• Create a Social Post and schedule it to publish on social media
• Create and activate an event
• Automatically send a series of emails when a contact joins your list
• "Ask a Trainer" Daily Drop-In Sessions
• Kickbox integration with Constant Contact
• Keeping clean contact lists
• View the location of your clicks in the Email Heat Map
• Use the Content Generator to write email, landing page, social, and SMS content for you
• SCORE

Meet Today’s Guest:

This episode features a wide range of small business owners who stepped up to the mic during our live Q&A sessions at the Constant Contact booth. From marketing agencies and HR consultants to spa owners, content creators, and market researchers, these entrepreneurs brought their most pressing marketing questions to the table.

In their conversation with Dave Charest, Director of Small Business Success at Constant Contact, each offered a different perspective on the small business journey. You’ll hear thoughtful questions about finding your audience, creating content that feels true to who you are, staying consistent with marketing efforts, and making technology work for you, not the other way around.

As Sophie put it: “I’m trying to figure out the best way to connect with people when I’m stuck in that introverted way.” That moment captured exactly what this episode is about, meeting business owners where they are, and helping them build confidence and clarity with every step forward.

These conversations were recorded live at the Small Business Expo events in Boston and NYC.

Aleah Carter: Marketing professional at Jillian Circus, a full-service digital marketing agency based in Long Island, NY 

👋 Where to find her: LinkedIn

David Williams: Founder of Triton Talent Solutions, an HR consulting firm focused on recruiting for small businesses 

👋 Where to find him: LinkedIn

Sophie Lee: Founder of a multimedia production company

👋 Where to find her: LinkedIn

Tatiana Guerrero: Director at Diamond Aesthetics Academy and co-owner of Diamond Skin and Body Spa in the North Shore area 

👋 Where to find her: LinkedIn

Alice Sungurov: Freelance content and marketing consultant exploring a business in art licensing 

👋 Where to find her: LinkedIn

James Saunders: Founder of EventAndTravel.com, a long-time event and travel professional based in NYC

👋 Where to find him: Instagram

Rob Hebron: Commercial real estate broker and third-generation partner in a family-owned firm

👋 Where to find him: LinkedIn

Martha Hayward: Founder of Bird Dog Insights, a market research company helping businesses better understand their customers

👋 Where to find her: LinkedIn

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