Five Roles Small Businesses Might Be Missing as Black Friday Approaches

An order has been sent to the wrong address. A customer is still waiting for a reply. A supplier has not confirmed whether an item is available, and yesterday’s returns have yet to be processed.

Each problem may seem manageable on its own. During the holiday rush, however, dozens can arrive at once, leaving a small business owner spending their busiest weeks clearing an inbox and correcting orders.

With Black Friday falling on Nov. 27, a remote hiring expert says businesses should start identifying these gaps now rather than waiting for sales to increase.

Data from VA Masters shows that a successful remote position takes a median of 18 days to close. That timeline does not include the additional time a new hire may need to learn the company’s products, systems and customer policies. The advice comes as the National Retail Federation forecasts total U.S. retail sales will grow 4.4% in 2026 to $5.6 trillion.

“When people picture holiday hiring, they usually think about someone packing boxes or serving customers in person. But the problems owners bring to us are often happening behind the scenes. The customer inbox is filling up, product listings have not been updated, suppliers need chasing, and nobody has checked whether the inventory system matches what is actually available,” said Alon Pearl, remote hiring expert and founder and CEO of VA Masters.

“Those jobs look small one by one, but in November they all arrive at once. September gives an owner time to show someone how the business works while things are still manageable. That is much easier than trying to explain the returns policy in the middle of the busiest week of the year.”

Pearl identifies five roles small businesses may need to have covered before the holiday rush:

1. Customer support assistant: Monitors customer messages, answers routine questions, and flags complaints or unusual requests. A growing backlog or longer response times can indicate that support is needed.

2. Order and returns coordinator: Checks order information, follows up on delayed deliveries, and manages return requests. This person can also make sure unusual cases reach the owner before they become customer complaints.

3. Inventory and supplier coordinator: Updates stock records, checks availability, and follows up with suppliers. This is administrative support rather than physical warehouse work, but it can help prevent customers from purchasing items that are no longer available.

4. Marketing operations assistant: Updates product listings, schedules promotional emails, and keeps the holiday marketing calendar on track. This can prevent planned promotions from being delayed because the owner is dealing with everyday operations.

5. Bookkeeping assistant: Organizes sales records, reconciles payments and refunds, and follows up on outstanding invoices. Keeping these records current can make the post-holiday accounting period more manageable.

“A small business does not necessarily need five new people. The owner needs to find the point where work is already starting to pile up. If customer messages are sitting unanswered, start there. If evenings are being spent correcting order records, that is the role to define,” Pearl said. “The aim is to have someone comfortable with the work before the rush begins, not to add headcount simply because the holiday season is approaching.”

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