Small Business Saturday

The holiday shopping season is about to kick into high gear. For merchant services professionals, this isn’t just a busy time for retailers—it’s the single best opportunity of the year to connect with new prospects and grow your portfolio.

While your prospects (small business owners) are prepping for the sales rush, you should be prepping your sales strategy.

Small Business Saturday is on November 29th. This gives you and I a perfect a two week window to get in the door. While your competition is sending cold emails, you have a warm, relevant, and urgent reason to talk to every merchant on your list.

This post isn’t about how to run a retail store. It’s a strategic guide on how to leverage the “Shop Small” movement to become a trusted advisor and sign more merchants.

Why This Day is Your “IN”

Small Business Saturday is a day when merchants are hyper-focused on one thing: maximizing revenue.

The stats prove it. Last year, shoppers spent a record-breaking $19.8 billion during this one-day event.

This is your “so what”:

• Merchants are thinking about payments. They’re worrying if their POS system can handle the rush, if their terminal is fast enough, and if high credit card fees are eating their profits.
• They are open to solutions. The pain of a slow transaction or a system crash is most acute right before the rush.
• You have a reason to talk. You’re not just “another salesperson”; you’re a consultant dropping by to ensure they’re ready for their biggest sales day.

Your 5-Step Sales Plan for Small Business Saturday

Forget cold calling. Use the next couple weeks to lead with value. Here’s your new playbook.

1. Lead with Value, Not a Pitch

Your opening line for the next 14 days is not “Can I save you money on processing?” It’s “Are you ready for the Small Business Saturday rush?”

Walk in or call with a helpful mindset. Share a simple tip:

“Hi Andy, I’m just stopping by to see how local businesses are prepping for Small Business Saturday. I know a lot of owners are running special ‘Shop Small’ promotions to get extra foot traffic. Have you planned yours?”

You instantly position yourself as a helpful advisor, not a sales rep.

2. Pivot “Experience” to the “Checkout Experience”

This is your most powerful pivot. A merchant’s great customer service can be completely ruined by a bad checkout.

• Ask discovery questions: “Where do your lines bottleneck when you get busy?”
• Highlight the pain: “A great experience can be lost in the last 30 seconds if the payment is slow or clunky.”
• Connect to your solution: “Are you set up to take tap-to-pay and digital wallets like Apple Pay? Shoppers expect that speed now, especially when it’s busy. Our newest terminals process transactions in under 2 seconds.”

3. Use “Online Prep” to Uncover Problems

Last year, 56% of Small Business Saturday shoppers made their purchases online. This is your “in” to talk about their e-commerce gateway.

• Ask about their site: “Are you expecting a lot of online orders, too? Have you stress-tested your online checkout?”
• Identify their frustration: “Nothing’s worse than paying for ads to get people to your site, only to have them abandon the cart because the payment page was slow or didn’t work on their phone.”
• This is a direct line to discuss their online gateway, security (TLS/SSL), and mobile payment optimization.

4. Be a Connector (and Bring a Gift)

This is your “foot in the door” tool. American Express provides free “Shop Small” marketing kits, decals, and tote bags. Use this as your reason to stop by.

“Hi, I’m just dropping off some ‘Shop Small’ resources for local merchants. I wanted to make sure you had the official Amex kit for your storefront.”

While you’re there, you have a perfect, non-threatening opportunity to look at their current setup.

• What terminal are they using? Is it old?
• Is their POS a modern, cloud-based system or a clunky legacy machine?
• Do they have a surcharge or cash discount sign up?

Take note of what you see. This is all intel for your follow-up.

5. Use the Amex Link as Your “Reason to Follow Up”

The link below isn’t for you—it’s for your prospects. Add it to your email signature. Send it as a “helpful” follow-up after a conversation.

This is a high-value, no-cost “leave-behind” that keeps you top-of-mind.

🛍️ Your Prospecting Tool: Free “Shop Small” Supplies

Here is the direct link to the American Express merchant supply page. Email this to prospects or use it to order kits yourself to hand-deliver.

Link: Order Free Merchant Supplies from American Express

Don’t Scrooge It Up!

It’s the season of joy, and for you, it’s the season of prospecting. Small Business Saturday gives you a warm, compelling reason to talk to every business on your route.

Don’t let this opportunity pass. Use this event to be a trusted advisor, solve a real, time-sensitive problem (slow checkout, high fees), and deliver an exceptional experience to your merchants.

Now, go help them prepare and grow your portfolio this holiday season.

Happy Selling,

David