When choosing a retail POS, start by assessing your business. Consider your annual revenue, store count, number of SKUs, and any services you offer beyond products. Small business POS systems may lack features you need, so list your must-haves and deal breakers. Key features might include inventory management, ecommerce integration, easy access to data and reports, and simple staff training. Lastly, consider your business growth. Your POS should offer 24/7 support, make it easy to expand to new locations, and provide regular updates to keep up with changes in retail.