How to Choose a Point of Sale System That Keeps Lines Moving

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You’re here to buy a point of sale system that keeps lines short, reconciles sales cleanly, and scales with your next store—without burning cash on the wrong setup.

Here’s the pain: confusing pricing and junk fees, credit card deposits that land late, terminals that freeze, weak uptime, and spotty Wi-Fi support. 

Inventory management that won’t sync with ecommerce, clunky exports, role permissions you can’t control, and hardware lock-in on card readers, receipt printers, cash drawers, and barcode scanners.

This guide shows you how to choose the right POS for a retail operation: cloud-based vs on-prem, payment processing and PCI, core functionality, mobile POS for in-person and curbside, integrations with CRM and loyalty, real-time reporting, and the support and SLAs to match your risk tolerance.

Use it to define must-haves, pressure-test vendors, and build a clean business case—so you implement once, onboard fast, and actually improve checkout and customer experience.

8 Things to Look for When Choosing Point of Sale Systems

Use this section to stress-test POS options against your real workflows—what actually happens at checkout, in the stockroom, and during close. 

The goal: buy once, implement cleanly, and scale without busywork or surprise fees.

1. Plan flexibility

Your needs change by season and store count—your pricing and packaging should keep up. 

Look for month-to-month terms, simple tier changes, and the ability to add users, registers, and locations without penalties or forced hardware bundles.

Check device and location limits, auto-renew and early-termination terms, per-feature add-ons, and promo expirations. Confirm whether historical sales data stays accessible after a downgrade and how quickly the POS provider can switch plans—get it in writing.

2. Data access and reporting

You need real-time sales reports you can actually act on—by store, register, cashier, product, and promo. 

Make sure you can customize dashboards, drill into margin and discounting, and export raw sales data without hoops.

Confirm data ownership, retention, and API access. You should be able to pull sales, inventory, and customer data into your BI tool, then schedule automated reports to inboxes for close.

3. Integration with your tech stack

Your POS has to sync cleanly with ecommerce, accounting, CRM, loyalty, and tax—no manual CSVs. 

Look for two-way, real-time updates for SKUs, prices, orders, returns, and customer profiles across in-store and online.

Ask about native connectors vs paid middleware, API limits, webhooks, and sandbox testing. If you change payment processing later, confirm the integration won’t break checkout.

4. Onboarding and support

Implementation should include data migration, SKU cleanup, receipt template setup, and hardware provisioning—card readers, receipt printers, barcode scanners, cash drawers. 

You want clear timelines, a migration plan, and named contacts.

Support must match retail reality: extended hours, fast SLAs, and multiple channels (chat, phone, email). Check the knowledge base quality, update cadence, and whether major releases come with change notes and training.

5. Role-based permissions

Tighten controls by role—cashier, keyholder, manager, admin—so only the right people can discount, refund, price-override, open the cash drawer, or view customer data. 

Require manager PINs for risky actions.

Look for audit logs, per-location permissions, and SSO support. You should be able to clone roles, apply across stores, and revoke access instantly when staff turns over.

6. Security and compliance

Protect cardholder data with PCI DSS-aware workflows, EMV, tokenization, and encrypted, cloud-based storage—never on a local device. 

Confirm device management for iPad or mobile POS and automatic security updates.

Ask about user session timeouts, IP restrictions for back office, and breach notification procedures. If you sell across regions, verify data handling aligns with your policies.

7. Customization and workflows

You should tailor screens and flows to your store—quick keys, custom tender types, receipt messages, taxes/fees, and order types (in-store, pickup, curbside). 

Make label printing and barcode formats painless.

Automate routine tasks: low-stock alerts, reorder points, customer prompts for email/loyalty, and end-of-day checklists. Bonus if the POS supports no-code rules to reduce manual steps.

8. Mobile and multi-location support

Modern POS systems need mobile muscle—iPad or handhelds with Bluetooth card readers, contactless payments, and an offline mode that still captures sales. 

Associates should do inventory counts and line-busting right on the floor.

For multi-store, expect centralized catalogs, per-location pricing and taxes, real-time stock lookup and transfers, and consolidated reporting. Adding a new store should be configuration—not a new project.

Take a break from research.

We make it simple:

1. Share your requirements
2. Discuss options with advisor
3. Receive a tailored shortlist
4. Get purchasing support

 

Share Your Requirements

How to Choose a Point of Sale System: A Step-By-Step Framework

Use this framework to move from “we need a POS” to a defensible decision. 

We’ll translate retail workflows into requirements, compare POS solutions apples-to-apples, and vet pricing, payment processing, and scalability—so you roll out once and see real-time gains across in-store and ecommerce.

Step 1: Identify your needs

Before demos, lock your requirements. 

Map how checkout, inventory management, and refunds actually run in your retail store, then decide which features and POS hardware—card reader, barcode scanner, cash drawer, receipt printers, iPad—are non-negotiable.

Gather stakeholder input

Talk to store managers, associates, finance, and IT. 

Capture friction at the register, deposit timing for credit and debit cards, mobile POS use cases (line-busting, curbside), and the back-office data needs—sales reports, customer data, gift cards, loyalty programs, and CRM sync.

List and prioritize pain points

Rank issues by impact: slow checkout, mismatched SKUs, manual stock counts, unstable Wi-Fi, clunky exports, or weak customer support. 

Tie each pain to a measurable outcome—faster transactions, fewer stockouts, cleaner sales data—to prove ROI.

Align with policies and goals

Confirm PCI DSS expectations, device standards (iPad vs fixed touchscreen), uptime/SLAs, and data retention. 

Note growth plans—new locations, kiosks, food truck, or omnichannel—and whether you prefer cloud-based POS systems with automatic updates over on-prem setups.

Differentiate must-have features

Lock essentials before pricing talks and keep the rest optional.

• Must-have (for most retailers). Core checkout and returns, accurate tax handling, integrated or flexible payment processing, offline mode, real-time inventory sync, role-based permissions, exportable sales data, and clean integrations with ecommerce and accounting.
• Nice to have. Advanced analytics, customizable receipt templates, no-code automation, loyalty and CRM depth, kiosk modes, and niche hardware extras like customer-facing displays.

Ask these questions:

• Top blockers. Document the three issues slowing checkout or breaking inventory accuracy, with examples from real shifts.
• Workflow coverage. Verify the POS supports your order types—in-person, pickup, curbside—and prints what you need on receipts.
• Data requirements. Specify sales data, inventory, and customer loyalty fields you must export or access via API on a schedule.
• Hardware footprint. List required devices—card reader, barcode scanner, cash drawer, receipt printers—and any USB-C/Bluetooth needs.
• Compliance and risk. Note PCI scope, user permissions, and who owns remediation if deposits fail or uptime slips.
• Scalability. Define the next 12–24 months—new stores, kiosks, or mobile POS—and how the right POS system should scale.

Step 2: Research point of sale system vendors

Scan the market to build a smart longlist, then pressure-test each POS provider against your business needs, pricing reality, and integration map. 

The outcome is a shortlist you can compare apples-to-apples—features, payment processing, support, and scalability.

Conduct high-level scans

Use reputable review sites, analyst roundups, and retailer forums to spot patterns—strengths, common outages, and support complaints. 

Note which modern POS systems are truly cloud-based, offer mobile POS, and support your core payment methods, gift cards, and loyalty.

Compare based on business needs

Filter by store count, SKU volume, ecommerce needs, and device preferences (iPad vs fixed touchscreen). 

Prioritize POS software that syncs inventory in real time, exports sales data cleanly, and supports your barcode scanner, receipt printers, and cash drawer.

Identify key differentiators

Look for transparent pricing, integrated vs third-party credit card processing, offline mode quality, API depth, and role-based permissions. 

Weigh implementation support, training, and customer support hours that match retail—nights, weekends, holidays.

Document findings

Track features, limitations, and total cost—software, payment fees, pos hardware, and add-ons—so nothing hides in the fine print. 

Keep notes on integrations tested, SLAs, and data portability for an easy exit if the fit changes.

Ask these questions:

• Pricing clarity. Request a sample invoice showing software tiers, credit card processing rates, statement fees, and any hardware leases.
• Integration coverage. Confirm native connectors for ecommerce, accounting, tax, and CRM, plus API limits and webhook options.
• Hardware compatibility. Validate certified card readers, receipt printers, barcode scanners, cash drawers, and kiosk or iPad setups.
• Reliability and SLAs. Ask for uptime history, planned-maintenance windows, and support response times during peak retail hours.
• Data ownership. Verify export formats, scheduled reports, and what happens to sales and customer data if you downgrade or leave.
• Contract terms. Check month-to-month vs long-term, early-termination rules, PCI responsibilities, and how price increases are handled.

Top POS Systems to Consider

Here’s my list of the top 10 point of sale systems options available, to help you get started in your search:

1. 1. Square — Best for ease of set up and use
2. 2. Stax Pay — Best for B2B sellers
3. 3. KORONA POS — Best for real-time inventory management
4. 4. Payment Depot — Best for high-volume businesses in various industries
5. 5. Shopify POS — Best for ecommerce businesses
6. 6. Lavu — Best for customization
7. 7. ePOS — Best for hardware bundles
8. 8. ShopKeep — Best for multi-location inventory
9. 9. Helcim — Best for high-volume businesses
10. 10. Clover — Best all-in-one system for small businesses

Overwhelmed by options? We can help.

Software categories, features, pricing… talk it through with a software expert who gets it.

Talk to an Expert

Step 3: Make a shortlist and reach out

Cut the noise to 2–4 vendors that fit your store count, workflows, and growth plan. 

Then run a tight, apples-to-apples process—pricing, credit card processing, integrations, and POS hardware—so you can pick a point of sale system with confidence.

Shortlist vendors

Choose contenders that match your must-haves: cloud-based POS, real-time inventory, solid ecommerce integrations, offline mode, and compatible hardware (card reader, receipt printers, barcode scanner, cash drawer). Research the best mobile POS systems to find options that meet these criteria.

Note why each POS provider made the cut—use cases, scalability, and total cost—so you can defend the list.

Send RFI or RFP

Ask for a sample invoice, processing rate sheet, contract terms, PCI scope, supported payment methods, hardware spec sheet, integration list, API docs, export formats, implementation timeline, and two retailer references. 

Request a sandbox or test tenant with sample SKUs and taxes, plus details on deposits, batch cut-off times, and uptime/SLAs.

Book demos

Run your script, not theirs. 

Have the rep complete real tasks: ring a sale with contactless payments, issue a return/exchange, apply a discount with manager approval, scan inventory in, transfer stock, process BOPIS, print labels and receipts, and complete an offline sale that re-syncs in real time. 

Test on your devices—iPad, Bluetooth scanner, receipt printer.

Use consistent criteria

Score each POS solution against the same rubric: must-have features, ease of use, integrations, reporting, customer support coverage, and total cost over 3 years—software, credit card processing, POS hardware, add-ons, and training when comparing enterprise POS systems.

Weight scalability for multi-location retailers and any seasonal or kiosk use.

Ask these questions:

• Apples-to-apples pricing. Share a sample invoice with software tier, per-location/register fees, processing rates, statement fees, and hardware costs.
• Payment flexibility. If we switch processors, what breaks—card readers, refunds, or reporting—and who owns PCI compliance.
• Implementation plan. Provide named contacts, migration steps, a cutover checklist, and realistic timelines for multi-store rollouts.
• Data access. Confirm export formats, API limits, webhooks, scheduled reports, and data retention after downgrade or exit.
• Hardware readiness. List certified card readers, receipt printers, barcode scanners, and cash drawers, plus offline mode behavior.
• Proof and references. Share uptime history, SLA targets and actuals, release notes cadence, and two retailers like us.

Step 4: Build the business case

Turn your research into a clear, defensible plan leadership can approve. 

Convert pain into dollar impact, outline total cost, and show how the right POS system improves checkout, inventory accuracy, and customer experience—fast.

Summarize pain points

List the top issues and tie each to an operational cost. 

Slow checkout means longer lines and abandoned baskets; mismatched SKUs drive stockouts and refunds; delayed credit card deposits squeeze cash flow. 

Add simple before/after metrics—average transaction time, inventory variance, chargebacks—so the benefits read like math, not marketing.

Present cost estimates

Show total cost of ownership by line item: software tier, per-location/register fees, payment processing (rates, assessments, statement fees), POS hardware (iPad, card reader, receipt printers, barcode scanner, cash drawer), data migration, training, and add-ons like gift cards or loyalty. 

Model 3–4 volume scenarios to capture seasonal peaks and “what if we add a store.” Use a transparent guide to POS system pricing to benchmark quotes and spot junk fees.

Articulate ROI

Translate improvements into revenue or savings: faster checkout throughput, fewer inventory errors, less manual entry, lower refunds, and higher attach rate via prompts and loyalty. 

Create a baseline, then a conservative projection, and define how you’ll measure—weekly sales reports, inventory accuracy, customer satisfaction, and deposit timing.

Ask these questions:

• Problem–impact link. For each pain point, state the cost today and the metric you’ll move with a new point of sale system.
• All-in pricing. Do quotes include software, payment processing, PCI scope, hardware, training, and support—no buried statement fees.
• Volume sensitivity. How do fees change at higher in-person volume, more locations, or new kiosks and mobile POS use.
• Cash flow reality. What’s the deposit timeline for credit and debit cards, and how are chargebacks and disputes handled.
• Time to value. What wins land in 30, 60, and 90 days—faster checkout, real-time inventory, cleaner sales data.
• Exit plan. If the fit changes, how do you export sales, inventory, and customer data, and what hardware remains usable with another POS provider.

Step 5: Implement and onboard your POS system

Roll out in phases, not chaos. 

Anchor the cutover on a clear plan, named owners, and training that mirrors real shifts—so day one feels boring in the best way and your retail POS actually streamlines operations.

Communicate rollout plan

Publish who does what, when. Include cutover dates, blackout windows, device setup for iPad or fixed touchscreen terminals, and how offline mode behaves. 

Document steps for card readers, receipt printers, barcode scanners, cash drawers, kiosks, and mobile POS—plus mobile payments, contactless payments, credit and debit cards.

Assign internal owners

Name a business lead, an IT/config owner, and a store champion per location. 

They own POS software settings, tax rules, user roles for employee management, payment processing deposits, and integrations with ecommerce, CRM, and loyalty programs. 

Give them direct lines to customer support and escalation paths.

Ensure consistent training

Train by role and task—ring an in-person sale, BOPIS, returns/exchanges, discounts with manager approval, gift cards, and loyalty enrollment. 

Use your real catalog, taxes, and promos, and record short videos. Track completion, then refresh before peak periods.

Create feedback loops

Stand up a simple intake for issues and ideas. Triage daily during the first two weeks, fix quickly, and publish internal release notes. 

Watch sales data and sales reports for early signals—throughput per register, refund rate, inventory accuracy, deposit timing, and customer satisfaction.

Ask these questions:

• Change management. What comms, deadlines, and job aids help associates adopt the POS without slowing checkout.
• Owners and escalation. Who approves config changes and who handles after-hours incidents with the POS provider’s customer support.
• Payment readiness. Have we tested contactless payments, mobile payments, credit and debit cards, and chargeback flows end to end.
• Training coverage. Do we have role-based modules for cashiers and managers, including gift cards, loyalty programs, and curbside.
• Hardware readiness. Are iPad setups, kiosks, touchscreen terminals, card readers, receipt printers, barcode scanners, and cash drawers tested with live tenders.
• Data and reporting. Are scheduled sales reports and exports set up for finance and ops, including CRM sync and real-time dashboards.
• Omnichannel fit. Does the rollout support ecommerce, in-store, and mobile POS use cases without duplicate work or data gaps.

Run Point on Your Search for a POS System

You’ve got the playbook—now run it. Use your must-haves, demo script, and scoring rubric to pick a point of sale system that speeds checkout, syncs inventory, and supports multichannel without surprises.

If you're in the process of researching point of sale systems, connect with a SoftwareSelect advisor for free recommendations.

You fill out a form and have a quick chat where they get into the specifics of your needs. Then you'll get a shortlist of software to review. They'll even support you through the entire buying process, including price negotiations.

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