POS Onboarding: The Complete Guide to Setting Up Your Point of Sale System

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When I first started implementing POS systems, I realized that onboarding is the part most people underestimate.

Everyone focuses on features, hardware, and pricing, but onboarding is where the success or failure of a POS rollout is decided.

If you're a business owner or operator looking to switch to a new POS or getting started with your first system, onboarding isn't just about setting things up.

It's about setting the tone for everything that follows—operations, staff productivity, customer experience, and even profitability.

In this guide, I’ll walk through every step of POS onboarding.

Whether you're in retail, hospitality, or run a franchise operation, this breakdown will help you streamline your rollout, avoid costly mistakes, and get the most out of your POS system from day one.

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Best Enterprise POS Systems of 2025: Our Top 5 Picks

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With so many POS options on the market, it’s easy to choose the wrong one — especially at the enterprise level, where mistakes are expensive.

We tested 15 of the most popular POS systems to find the ones that actually scale with your business.

Whether you're managing 10 stores, running a high-volume restaurant, or expanding from ecommerce into physical retail, these platforms are the best in the game for 2025.

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Most Important POS Features Every Retailer Needs

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When I first started digging into POS systems, I figured they were all kind of the same — scan, swipe, done. But it didn’t take long to realize how much more there is under the hood.

A modern point-of-sale system isn’t just about taking payments. It can help you manage inventory, track employees, sync online and offline sales, and a lot more.

In this guide, I’m breaking down the most important POS features that retailers should be looking for.

Whether you're opening a new store or upgrading from an old system, these are the tools that will actually make a difference in your day-to-day operations — and your bottom line.

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Best POS Systems for Convenience Stores (2025)

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With over 150 hours of testing and comparing 10 leading POS systems specifically for convenience stores, I’ve narrowed down the top five that stand out for usability, pricing, features, and reliability.

Whether you're running a neighborhood shop or managing multiple locations, the right POS system can seriously improve your checkout process, inventory control, and profit margins.

Our Top 5 POS Systems Square for Retail – Best overall POS Nation – Best for age-restricted items Clover – Best for design and ease of use Lightspeed Retail – Best for growing multi-location stores Toast POS – Best for C-stores with hot food

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How Much Does a Cash Register Cost?

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One of the first questions I had when starting a retail business was how much I’d need to invest in a cash register or POS system.

It’s a simple question, but the answer depends on a lot of moving parts—type of business, budget, volume of transactions, and how much you want your register to do.

Whether you're opening your first store or upgrading your current setup, understanding the real cost of a cash register is key.

Below, I break down the different types of registers, pricing ranges, and what influences those costs—from hardware to software and everything in between.

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Best Ecommerce Certifications for Retail: Learn What Actually Works

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When I first made the jump from running a brick-and-mortar store to selling online, I had no idea how complicated ecommerce could get. I thought setting up a store on Shopify or WooCommerce was the hard part. I was wrong.

Syncing inventory between online and in-store sales, getting paid correctly, running promotions, managing returns, setting up shipping—every piece had to work together.

And unless you’ve got a strong handle on how ecommerce actually works, it’s easy to waste money on tools you don’t need or make decisions that create problems down the line.

Certifications helped me cut through all of that. They showed me what mattered, what didn’t, and how to set up a system that works for my type of retail business.

In this guide, I’ll walk you through the best ecommerce certifications for retailers, how they work, how much they cost, and which ones are actually worth your time.

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Best Retail Business Podcasts: My Go-To List for Staying Sharp in Retail

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As someone who’s worked in retail for years and is constantly keeping an eye on trends, I can tell you this: podcasts have become one of the best tools for staying informed without needing to carve out hours for reading or research.

Whether I’m unpacking boxes, managing POS software updates, or doing end-of-day reporting, I’ve always got a podcast running in the background.

Over time, I’ve curated a list of the best retail business podcasts that are worth listening to—especially if you’re serious about running a tight, profitable retail operation.

In this post, I’m breaking down the ones I actually listen to.

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How to Open a Retail Store: A Step-by-Step Guide with POS in Mind

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Opening a retail store is exciting, but it’s also complex.

I’ve worked with retailers who had everything lined up—great branding, a product people wanted, even funding—but they still failed because they skipped the basics or underestimated the role of technology.

If you’re thinking about starting your own shop, whether it’s clothing, electronics, books, or specialty foods, this guide breaks everything down step-by-step.

We’ll also focus heavily on your point-of-sale (POS) system and how it fits into the bigger picture.

Here’s what you need to know before you open your doors.

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