A customer steps up to the counter with a cigar or a pack of papers — a small sale that keeps your shop running. But what if every one of those transactions could earn a little more?
That’s the power of upselling and cross-selling. These techniques help customers discover complementary or upgraded products while driving higher profit margins for your business. Research shows that upselling can raise revenue by 10–30%, increase customer lifetime value by 20%, and is 68% more cost-effective than finding new customers.
Here are five upsell strategies that make everyday sales more profitable and how point of sale (POS) data helps you apply them more effectively.
1. Product Bundling for New Cigar Smokers
New cigar smokers are curious and ready to buy, but most don’t know what they need for the full experience. Bundling, which involves packaging related items together for one price, is a natural way to upsell and cross-sell.
Build top-selling bundles with these tips:
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Start with experience kits: Pair a few mild cigars, like a Macanudo Café or Montecristo White, with a cutter and lighter so first-timers leave with everything they need to get started.
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Group by taste or origin: Organize sampler packs by flavor strength or by region, like Nicaragua or the Dominican Republic, to encourage exploration without overwhelming choices.
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Add simple upgrades: Include a small humidifier or travel case so customers understand the importance of storage — and return later for refills.
This upsell strategy makes new customers feel guided and welcomed, and helps your shop turn a first purchase into lasting loyalty and higher sales.
2. Impulse Items at the Checkout Counter
Many store owners think cigar retail upselling means long conversations or pushy pitches. In reality, some of the best upsells happen silently — through small, irresistible items placed right where customers pause to pay.
Try these quick wins:
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Feature grab-and-go favorites: Place torch lighters, travel humidors, or single cigars at the counter to turn a simple purchase into a multi-item sale.
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Show limited runs: Display seasonal cigars like Alec Bradley Black Market Filthy Hooligan or exclusive blends that invite quick, last-second upgrades before checkout.
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Create a power wall: Stock a small self-service rack with high-margin accessories near the register, giving customers a subtle push to pick up one more item as they check out.
Research shows that point of sale displays can lead to four times as many unplanned purchases — proof that subtle design can drive steady, effortless upselling.
Education is one of the simplest upsell strategies to move high-end products. The right messaging can earn you 40-60% higher margins on luxury rolls, with up to 300% markups on some rare or collectors’ releases.
Here’s how to encourage top-level purchases:
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Create quick-read signage: Add short notes about flavor, tobacco type, or origin beside artisanal cigars to draw attention to craftsmanship and help customers see the value behind the price.
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Share cigar care tips: Use your email newsletter or website to teach customers how to cut, light, or store cigars properly. This will show your expertise and build interest in higher-quality selections.
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Host short demos: Offer brief, in-store sessions that show how premium cigars burn slower or taste richer, giving shoppers a reason to trade up on the spot.
When sharing educational content, remember to follow tobacco store marketing rules. Limit social media posts to factual, adult-focused information and avoid anything that might appeal to minors.
4. Training Cashiers To Recommend the Right Products
The checkout counter is your frontline for upselling. Equip your team with simple, repeatable techniques that turn small purchases into higher-value sales.
Train your team to:
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Ask, then guide: Teach staff to ask what a customer enjoys, then suggest a small upgrade: “If you like the Oliva Connecticut Reserve, you might enjoy the Perdomo 10th Anniversary Champagne,” or “This jet torch pairs perfectly with your pick.”
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Share personal picks: Encourage employees to discuss cigars, lighters, or humidors to build trust and turn casual interest into confident purchases.
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Acknowledge every win: Highlight when someone turns a routine checkout into a larger sale — recognition reinforces good habits and keeps the team engaged.
49% of shoppers report making an additional purchase when it’s personally recommended. Use your point of sale data to guide tailored suggestions and connect those moments to your loyalty program so every upsell builds repeat business.
5. Strategic Promotions That Move Customers Up the Ladder
Tobacco store promotions don’t always mean discounts or giveaways — design offers that double as upselling strategies. The best ones encourage customers to explore, upgrade, and spend more each visit.
Give shoppers a reason to try higher-margin products while keeping value intact with these ideas:
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Mix and match offers: Pair premium cigars like the Arturo Fuente Hemingway with midrange staples such as the CAO Gold, so customers can compare flavor and step up next time.
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Spend-more bonuses: Reward larger purchases, like spending $75 or more, with a free cutter, refill butane, or branded accessory to make upgrades feel rewarding.
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Loyalty milestones: Offer exclusive bundles or early access to new arrivals for your most consistent buyers.
Strong promotions turn curiosity into bigger sales and repeat visits, combining upselling, cross-selling, and loyalty in one move.
Grow Revenue With Data-Backed Upsell Strategies
Upselling can raise ticket size and strengthen customer loyalty, but pairing it with data and automation takes it to the next level. With the right tools, you can identify buying patterns, see which products sell together, and train your team to make smarter recommendations every day.
Cigars POS is a purpose-built solution for tobacco store owners. The software lets you:
- Track bestselling items and see which combinations drive the most profit.
- Identify high-margin products perfect for bundling or cross-promotion.
- Set automated prompts for staff to suggest related items at checkout.
- Manage inventory by flavor, size, or brand to avoid stock gaps.
- Measure promotion results and customer response in real time.
These data insights guide every sale, making upselling easy, consistent, and repeatable.
Bring effective upsell strategies to life. Download The Tobacco Point of Sale System Buyer's Guide to learn how to choose the best solution and how Cigars POS can turn everyday purchases into long-term revenue for your tobacco shop.
