For small businesses capitalising on its popularity and name recognition, it creates a surge in opportunity as well as stress for sales teams. Major sales events hit smaller teams harder. They have fewer resources, tend to have more manual work involved than their enterprise-sized peers, and as a consequence, may face steeper challenges if things go wrong in delivery, fulfilment, and returns. Moreover, there are signs of creeping sales periods as retailers react to pressure and start their Black Friday deals earlier.

It’s a well-worn truism that success relies not just on your people, but the systems, strategy and the smart use of data to win leads and make sales in the 2020s. The key is to maintain a strong grip on the fundamentals of commerce while taking advantage of the changing features of the technology and nature of data available to retailers – among everything else in the volatile economy.

It’s Black Friday, not Bleak Friday

First off, ensure the human factor is looked after. Salespeople and all staff in charge of service are there for a reason. If the business or sales situation puts them under mental strain it increases the risk of errors and burnout over the vital golden quarter.

All the common issues that plague business processes are to an extent avoidable with care or the right tool set for the job/environment. E.g. missed follow-ups, inbox overload, or – horror – clunky spreadsheet-based tracking that all-but guarantees errors will follow.

It’s important to learn from past mistakes or where to improve. Regularly look at processes for clarity and reasonability. Ask peers and tech partners for information on what tools reduce mental load and free time for high-value conversations and contribute to serving the bottom line.

Is your tech stack ready?

For most retailers, events like Black Friday often expose cracks in their digital systems. Famously, major issues include slow website loading times or dropping orders under high volume pressure. Customers don’t immediately see issues with CRM functionality, or poor integration with marketing platforms that cause strain in the back office, but these types of issues just make the process of working more time-consuming and stressful than it should be. It’s these ‘niggles’ that contribute to unhappiness and employee churn.

Right now, AI (often powered by LLMs) is the hot tech topic of the moment. But AI isn’t necessarily the be-all of tech. More simple, mature, and reliable automations can handle admin tasks, freeing teams to focus on closing deals and responding to customer enquiries. Automations exist across the tech stack, often incorporated within SaaS services, perhaps as add-ons, and offer human time-saving benefits. For example: Workflow automation. Drip campaign automation with email templates. Chatbots for lead nurturing. Lead scoring automation. Automatic lead assignment and revenue forecasting.

A past Pipedrive State of Sales and Marketing report revealed that people who automate tasks are 16% more likely to hit their targets. Anything that speeds up performance and/or improves accuracy contributes to a real-time visibility into the pipeline which helps managers spot issues early and course correct before any niggles spread by word of mouth or social media affect the funnel.

If you do decide to incorporate AI to better support the sales process, consider adding features into existing business processes as part of a five-step approach:

1. Optimise sales prospecting – review your data across sales, where have the biggest spikes in purchases been, what products have been flying and which ones haven’t? This retrospective oversight can help uncover new audiences through predictive analytics, social listening, and market analysis
2. Personalise outreach – analyse customer behaviour, what trends are you noticing for individuals and their unique product preferences? Gauge the success of past interactions and build on that
3. Streamline lead scoring – parse customer data and prioritising leads based on the likelihood they will convert; a traffic light or grading system will help you see where your time is best spent
4. Improve sales forecasting – start reviewing historical data, customer feedback and reviews, alongside market trends to offer more accurate revenue supply and demand predictions and planning
5. Be agile – overall, aid in making smarter and faster decisions, be quick with your insights and strategy. Customer needs should be met swiftly, otherwise you can miss out on a sale. Leaders can use all these example use cases to make data-driven decisions

Strategy traps, buyer signals, and getting out ahead

Discounting can drive short-term volume but harm long-term value if poorly managed. Misjudging volumes is a terrible situation to be in.

High-volume sales events generate valuable behavioural data on who’s hesitating, abandoning carts, or revisiting offers. But Black Friday prep starts long, long before.

Spotting and acting on purchasing signals enables more personalised and timely follow-ups. Even small teams can apply this insight through triggered reminders or automated outreach. Priming followers with social media posts/activities, or encouraging specific email sign-ups, helps indicate potential interest. Sales leaders can then judge the impact on commission structures, and pipeline forecasts. Using signals for scenario planning helps teams avoid knee-jerk decisions on pricing or resourcing when under pressure.

Black Friday, Christmas, new year sales, and beyond

Small sales teams will thrive in peak periods with the right preparation and tools. As 2025 rolls into 2026, the current pressures of inflation and instability are likely to continue. Retailers should ensure they are not working ever harder to convert leads and make sales.

Rather, success comes from structuring resources, people, business processes, and smart tech to work together to relieve pressure at peak times, ensuring that customers are brought through the sales funnel and looked after to maintain interest into the future.

Burnout is unproductive and can only damage the business. Plan, lay the groundwork for success early, and ensure all the elements of the business support great customer experience for a truly golden quarter, and a profitable 2026.

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