Stop Annoying Customers — Here’s How to Automate the Right Way

There’s plenty of places you can streamline or personalize your operations without losing that human touch.

By Liz Brody • Sep 23, 2025

This story appears in the September 2025 issue of Entrepreneur. Subscribe »

This article is part of the America's Favorite Mom & Pop Shops series. Read more stories

In the past, customer service looked like this: If you were a big company, you could afford enterprise-grade technologies. And if you were a mom-and-pop shop, you were left to chitchat at the register.

Now, things are different. Customer personalization tools are widespread and affordable. A bakery on the south side of Pittsburgh, for example, used one to send shoppers messages like: “Hey Jim, It’s your birthday! Come have a pastry on us.” A beauty salon automatically emailed a product offer based on the service a client just had. A fitness studio lured back members with motivational quotes and customized reengagement offers.

“Customer personalization is tailoring your website, marketing, messaging, or offers to an individual user based on their behavior, preferences, demographic information, and past interactions,” says digital marketing consultant Chris Essey, who specializes in helping hyperlocal businesses.

He often equips his clients with the best tools for them. Here, he recommends his top four for small business owners.

For do-it-all help…

“If I was to recommend just one out-of-the-box solution for any small business, it would be HubSpot,” says Essey. It’s easy to use and does just about everything you need: You can create different landing page content depending on the individual user, send personalized emails, write customized social posts, and capture customer data. “They also have a really good support staff.”

For better email marketing…

When it comes to masters of the customer inbox, it doesn’t get better than Mailchimp, says Essey. It’s simple to use for sophisticated tasks like targeted emails based on a customer’s demographics, behavior, and purchase history, as well as drip campaigns — where, depending how the customer interacts with the first email, it will send a different follow-up message. “If email is the only thing you need done, Mailchimp’s the way to go,” says Essey.

For growing direct-to-consumer…

Klaviyo goes deeper into email personalization for e-commerce than HubSpot and Mailchimp, and integrates closely with platforms like Shopify and BigCommerce. For example, Klaviyo can automatically send out abandoned cart reminders with product recommendations and, after a purchase, create email flows that ask for product reviews or offer discounts on related items.

For generating leads…

To grow a subscriber list or convert website scrollers to buyers, OptinMonster allows you to create pop-ups, slide-ins, and other opt-in forms tailored to individual visitors that can collect email addresses and display the right offer to the right person. “It’s also a great opportunity for mom-and-pops to customize messages to bring users into the brick-and-mortar store,” says Essey.

But he also offers a word of caution: Although these tools are great, they should not fully replace a personal touch. “If a coffee shop sent me a handwritten card saying, ‘Hey we’re so happy you came in,’ I would be like, ‘I’m never getting coffee anywhere else.'”