The Art of the Upsell: Teach Servers to Increase Average Check Amounts

You want to make more profit. Your servers want to make more tips. A crash course on upselling is a win-win for everyone.

Your servers might not realize it, but their words have a lot of power. Knowing how to present a higher shelf vodka or a premium side could make a world of difference for their wallets.

And beyond the increased checks, pro servers who are able to successfully upsell are also recommending your restaurant’s very best for guests. Those bigger ticket items are often your best dishes or most unique cocktails that will stand out in guests’ minds and make for an elevated dining experience.

Here are a few ways your servers can gently suggest some pricier upgrades that will boost their average check size, making everyone a few extra dollars.

1. Consider your memorable dining experiences

Before you dive into our upselling go-tos, take a minute to reflect on your last really good experience at a restaurant and how your server’s language, attitude, and knowledge affected your experience.

Did your server walk right up and ask if you want an appetizer? Or did they take the time to talk through specials, field questions about menu items, and give you the space you needed to make a decision?

Was your server’s demeanor generally excited and upbeat? Or did they actually look a bit disappointed when you said you’d just be having water?

These small, unspoken cues are what make or break a server’s night. Leading with confidence, positive energy, and genuine concern for your guests’ experience is what will build trust between server and customer, so they’ll be more open to suggested upgrades.

2. Value authenticity

Upselling just for the sake of a higher tip is not a successful strategy.

Remind your servers that while upselling can improve guest experience and your tip, it’s important to flex to the needs of your guests. Don’t continue to push higher priced items if guests are starting to look uncomfortable.

They say the most successful salespeople believe in what they are selling — and the same goes for servers. Your servers should have tasted all of the higher priced menu options and be able to explain to guests why this upgrade brings their dining experience to the next level.

3. Start with the drinks

Alcohol sales are restaurants’ bread and butter. So when a table orders the first round, servers should make it count.

Scenario #1: A customer orders a simple spirit + mixer drink

If a guest asks for a vodka soda, this is an opportunity to turn a $10 drink to $15 or even $20 — which will add up after a few rounds.

Naturally, most servers would ask what vodka the guest prefers. Teach your servers to resist that urge! Instead, servers should offer them a selection of higher-shelf options. For example, a server could respond with, “Vodka soda? Sure, would you like that with Tito’s, Ketel One, Grey Goose…?” And keep listing options until one resonates with the guest. That gives the guest the impression that they have a seasoned, well-informed server, but this framing also leads the customer to choose from the higher-shelf suggestions, rather than just asking for the house vodka.

Scenario #2: Ordering a glass of wine

We’re not suggesting you hire a sommelier, but getting more familiar with common flavor profiles and notes in wine can be a game-changer for servers’ nightly tip income.

Customers often ask for something similar to pinot grigio, cabernet sauvignon, or a pinot noir, and if their server can give a detailed description that makes a wine sound irresistible, they’re probably going to splurge for the higher-end wine. Bonus points for servers who can successfully suggest splitting a bottle (because once they taste it, they’ll want more than one glass!).

Consider hosting a weekly wine training to help your servers get more familiar with what your bar has to offer. Another pro-tip: Teach your servers about beer and wine pairings! When servers let guests know which entrees pair well with the drink they’ve ordered, guests may opt for a higher-priced entree to match their favorite beverage.

Don’t skip over the apps

Not everyone is going to order an app — but there are a few small changes servers can make to their dialogue with customers to convince those who wouldn’t normally spring for a first course.

For one, servers shouldn’t just ask if they’d like anything to start. Instead, teach your servers to approach tables with a suggestion for a specific menu item. For example, they could say, “Would you like a charcuterie board to start? We just added a really delicious local cheddar to our rotation.”

Offering patrons a specific menu item and talking up the details makes it a lot easier to add that extra course to their meal — increasing their check size and making it more likely that they’ll order a second beverage.

Taking the order

When it’s time to take the entree order, this is your servers’ time to shine. Just like the previous courses, they should know how to create opportunities to upsell guests by making entree upgrades too enticing to pass up.

From fine dining to fast casual, many American restaurants offer a burger on their menu. Rather than simply asking, “Great, are fries ok with that?” task your servers with turning a simple cheeseburger into a deluxe meal with several upsells.

First, make sure your staff knows your menu options well, so they can pass along those options to customers. Here are a few common upgrades that servers should be asking guests if they would like:

Pretzel or gluten-free bun
Added cheese
Premium toppings, like bacon, egg, avocado, etc.
A premium patty, like bison or imitation beef

Rather than asking if fries are okay, instruct servers to say, “What side would you like? We have french fries, macaroni and cheese, caesar salad…” and continue with options until one piques the guest’s interest. If they succeed in getting at least one upgrade to a customer’s burger and a premium side, the check can increase by around $4 per person, depending on the pricing at your restaurant.

Higher-end restaurants should follow the same formula, subbing in an option for steak oscar rather than a bacon cheeseburger. The goal is for servers to provide options for guests who may not realize that their favorite accoutrement is on the menu — and will gladly pay for the upgrade.

The grand finale

“Did you save room for dessert?”

Servers often bring out this line while pre-bussing tables, usually expecting guests to say that they’re far too full to even think about dessert. If you want to convince more guests to stick around for a final course, ask your staff to remove that phrase from their vocabulary.

Dessert is a rich treat for the senses that most of us crave at the end of the night, so servers shouldn’t treat it like an afterthought in front of customers. As they’re clearing away dishes, servers can tap into their senses by talking about your pastry chef’s perfect chocolate cake with buttery layers of icing, or the warm peach cobbler served with house-made vanilla ice cream on the side.

Even if guests seem like they’re truly full, your team can still offer them a slice to-go, since they’ll surely be wishing for something sweet in about an hour anyway.

Reap the rewards

After putting on their best smiles, connecting with guests, and using these upselling tricks, your servers should ring in above-average size checks — and an above-average amount of tips.

Once your servers see their huge tip out for the night, they’ll want access to those funds ASAP. At Kickfin, we provide instant digital tip payouts, so managers don’t have to waste time counting cash and servers can clock out of their shifts sooner.

Check out a demo of Kickfin today.

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Product and Company News

Kickfin Makes the 2026 Inc. 5000 — Again. And We’re Just Getting Started.

For the third year running, Kickfin has been named to the Inc. 5000 — Inc. magazine’s definitive ranking of the fastest-growing private companies in America — earning our place once again among the fastest-growing companies in restaurant and hospitality technology.

Three years on the Inc. 5000 isn’t a lucky streak. It’s a scoreboard — and it says the same thing every year: the industry is moving off cash, and it’s moving to Kickfin.

Restaurants and hospitality groups are walking away from cash tip-outs, spreadsheets, and pay cards — and they’re not looking back.

Growth that’s built on getting operators out of the cash business

Three straight years on this list is the result of one simple idea taking hold across the industry — but the metric we’re proudest of isn’t ours. It’s our customers’.

Operators are trading 3 a.m. bank runs, $10,000 in the safe, and 45 minutes of manual tip math per shift for something that takes seconds. Southern Proper Hospitality went from three to four bank runs a week to one a month. RA Ventures — 55+ locations across three brands — handed managers back the four hours a night they used to lose to counting cash and paperwork, and eliminated bank runs entirely. At one of its concepts, 98% of employees opted into instant payouts the moment they had the choice. That’s not a software win. That’s giving managers their nights back — and employees their money faster.

We hit this ranking through a stretch that tested every operator in the country: labor shortages, rising costs, and razor-thin margins. Kickfin grew because in that environment, cutting hours of admin and eliminating cash risk stopped being a nice-to-have and became survival.

Why operators keep choosing Kickfin

Three things separate us in a category we’ve defined:

Tips go straight to the bank account employees already have. No proprietary card. No transfer fees to touch their own money. No credit checks, no age restrictions, no financial product nobody asked for. Marco’s Pizza chose Kickfin specifically to avoid handing staff a pay card. Rock N’ Roll Sushi eliminated the $1.50-per-shift fee employees were paying just to access their own tips somewhere else.

Tip math is calculated straight from the POS. Toast, Square, Micros, Lightspeed, R365, Union, SkyTab — Kickfin reads the shift data and calculates pools and shares automatically. No exports, no whiteboards, no “trust me, I did the math.”

Every payout is on an auditable digital ledger. Complete history by location, shift, and employee. When it’s time to answer a compliance question, the answer is already there.

The bigger story: this was never just about tips

Here’s what the ranking really signals. What started as the best way to pay out tips has become the disbursement infrastructure the hospitality industry runs money through — POS-native, API-first, and built for 50-state payroll compliance from day one.

Payroll and HCM platforms have noticed. Companies like iSolved, Auris, Adora, Netchex, and AllianceHCM are embedding Kickfin’s API to deliver instant tip and wage disbursement to their own restaurant customers. We’re not a feature bolted onto someone else’s stack — increasingly, we are the stack.

And we’re not slowing down. Something big is coming in early 2027 — the next chapter in how Kickfin moves money for the hospitality industry. We’re not ready to show all of it yet, but if the last three years are any indication, it’s worth watching this space.

The Inc. 5000 measures how fast a company has grown. What it can’t capture is why: we’re building the rails for how the entire hospitality industry pays its people. The tip management category is ours to lead today — and it’s only the beginning of what Kickfin is building.

Thank you — you built this list

Every place on the Inc. 5000 is really thousands of shift-end tip-outs that went off without a hitch, thousands of bank runs that never happened, and thousands of employees who got paid instantly and fairly. That’s on our customers. We owe this ranking to the operators who trusted us with the least glamorous, highest-stakes 20 minutes of their night — and to the teams who show up for them beyond business hours, because restaurants don’t clock out at 5.

We’re honored to be on the 2026 Inc. 5000. We’re more excited about what we’re building next.

See why the fastest-growing restaurants are ditching cash tip-outs for good. Book a demo →

Product and Company News

2025 Roundup: Your Favorite New Tip Management Features

2025 was a defining year for Kickfin and the customers who rely on our software to automate their tip management processes

Driven by direct customer feedback and the evolving realities of restaurant operations, our Product Development team delivered a wave of meaningful enhancements across tip calculation, integrations, user controls, and accounting.

Before we look ahead to 2026, here’s a look back at the product advancements that made Kickfin more robust, more flexible, and more ready to meet the demands of restaurant teams than any other tipping solution.

Advanced Tip Calculator Enhancements

n 2025, we significantly expanded the functionality of Kickfin’s Tip Calculator. Here are a few standout features that we released:

Separate Tips and Auto-Gratuities

Kickfin now tracks tips and auto-gratuities separately, allowing operators to report them independently to payroll and manage them differently for tax purposes.

This distinction is especially important in light of the 2025 No Tax on Tips legislation. While tipped employees no longer pay federal income tax on the first $25,000 in tips earned annually, auto-gratuities, service fees, and other compulsory charges remain taxable.

Kickfin ensures those earnings are categorized correctly from the start — reducing downstream payroll and compliance risk.

House Accounts for Service Charges

Not all service charges are distributed 100% to employees — and Kickfin allows you to handle that with “House Accounts.”

Operators can retain a portion of service charges while distributing the remainder to the team. This is particularly valuable for:

Special events and private dining
Paying out job roles that don’t typically participate in tip pools (e.g., event managers)
Maintaining clarity and transparency around service charge allocation

More Flexible Tip Share Logic

No two restaurants share tips the same way — and Kickfin’s calculator now supports even more real-world scenarios.

Operators can configure tip shares:

By shift or by check close, ensuring support staff are compensated appropriately even if they didn’t touch a specific check
By hours worked or split evenly, a level of flexibility that remains unique to Kickfin
With advanced rules for “remaining tips,” allowing operators to define how servers and bartenders split earnings after support positions are paid out.

These enhancements allow Kickfin to support everything from simple pools to highly complex policies.

Check-Level Edits for Greater Accuracy

POS data doesn’t always capture every nuance, so managers may need the ability to make changes.

Kickfin now supports individual check-level edits for:

Cash tips
Auto-gratuities
Check details and splits

This ensures large parties, special events, and edge cases are handled accurately.

Tip Calculator Change Log for Auditability

Any check-level change made by a manager is recorded in a detailed change log. This creates a clear audit trail, helping operators resolve questions quickly and reinforcing transparency and trust with staff.

Enhanced Functionality for Smarter Cash Handling

Thousands of restaurants use Kickfin because they don’t have enough cash on hand to pay out credit card tips, and they want to reduce the amount of cash handling in their restaurant altogether.

However, we know cash will probably always be a (small) part of the equation. Kickfin makes it easy for you to handle that with some added functionality:

Tips left in cash: If a diner leaves a pile of cash at your table, it might not get recorded in your POS. However, Kickfin allows you to record it and distribute it through our platform.
Cash payouts: Many operators may want to distribute all of the cash left in their register at the end of a business day to avoid bank runs for deposits. Again, that’s easy to do with Kickfin’s “Blended Payouts” feature.

Enhanced Support for Toast Delivery Service Tips

Kickfin now handles Toast Delivery Service tips more intelligently by excluding driver tips from the general tip pool and assigning those tips directly to the delivery driver. This ensures tips are distributed exactly as intended.

Kickfin delivers on all of those fronts by:

Freeing managers up from bank runs and the back office, so they can focus on everything that can’t be automated.
Ensuring employees walk out the door with their earnings already in their existing bank account, no waiting, no detours.
Helping operators stay compliant, track everything, and uncover new efficiencies.

Expanded POS and Payroll Integrations

New POS Integrations

In 2025, we expanded our POS ecosystem with new integrations including Union POS and rPOWER. POS integrations eliminate manual uploads, reduce errors, and enable real-time tip calculation and reconciliation. Learn more about integrating your POS with Kickfin.

New Payroll Integrations

We also launched new payroll integrations with ADP Run, Paylocity, and Restaurant365 Payroll.

Once activated, Kickfin generates export files that sync seamlessly with your payroll system — significantly reducing manual work for payroll teams.

Looking Ahead

platform that keeps pace with the ever-changing complexity of modern hospitality operations.

If you’re not yet using Kickfin, now is the time to see what advanced tip management really looks like 👉 Schedule a demo today!

If you’re already a Kickfin customer, our team is happy to walk you through what’s new. 👉 Schedule a quick consult to learn more.

And of course: Stay tuned for what’s to come in 2026!

Product and Company News

Kickfin Named to Deloitte Technology Fast 500 List for Second Consecutive Year

Kickfin is proud to announce that we have once again been named to the 2025 Deloitte Technology Fast 500™, a ranking of the fastest-growing technology, media, telecommunications, life sciences, fintech, and energy tech companies in North America, now in its 31st year.

Kickfin is the only company on the list purpose-built for restaurants and bars to automate tip management — marking another major milestone for our team, our partners and the thousands of restaurant operators who trust us to modernize their tip-pooling and payout workflows.

Why it matters

When it comes to tipping out employees, cash is no longer king — and needs are changing fast. Hospitality workers demand (and deserve!) faster, cashless payouts; burned-out managers need more hours in their day; and now more than ever, operators care about visibility, compliance, and employee satisfaction.

Kickfin delivers on all of those fronts by:

Freeing managers up from bank runs and the back office, so they can focus on everything that can’t be automated.
Ensuring employees walk out the door with their earnings already in their existing bank account, no waiting, no detours.
Helping operators stay compliant, track everything, and uncover new efficiencies.

What sets Kickfin apart

There’s a reason Kickfin is the best-in-class tip management solution.

Broader POS integrations: We’ve expanded our direct integrations with leading POS brands, including Toast, Square, SkyTab, Genius POS, Union, and more — so managers can pool and pay out tips in a matter of clicks.
Enhanced tip-pool logic and flexibility: Our platform automates even the complex tip pool policies, with more tip pooling and automated reconciliation features than any other solution, while keeping the end-user experience simple and intuitive.
Instant, cashless payouts: With fewer cash drawer runs and real time bank deposits, teams experience faster shift-close, fewer errors and improved satisfaction.
Built-in compliance and reporting: As tip-pooling regulations continue to evolve, Kickfin empowers customers with robust features like digital paper trails and payroll integrations to ensure accuracy and compliance from end to end.
Customer success focus: Our fully U.S.-based Customer Success team is partners with customers to make onboarding fast and easy, no matter how tricky your tip policy may be, so you get ROI right away.

A big thank you

We’re honored to be recognized by Deloitte, and even more excited about what comes next. For restaurant operators, managers and employees alike, the future of tip management is here, and we’re thrilled to be your partner.

Ready to see what automated tip pooling and instant payouts look like in action? Book a demo today!

Product and Company News, Technology and Software

New Kickfin Feature Alert: Blended Payouts Are Here!

Brand new feature, coming in hot!

As part of our latest product release, Kickfin now offers Blended Payouts for even easier, fully automated tip management and reconciliation.

Why Blended Payouts Matter

Now more than ever, restaurant guests use credit cards or digital payment methods instead of cash. For many operators, that means there isn’t enough cash on hand at the end of a shift to pay out tips. But employees still want to receive their payouts immediately after clock-out.

As our customers know, Kickfin solves for those cash shortages by automating and digitizing the payout process — giving you the power to send instant, cashless payouts directly to your employees’ bank of choice, 24/7/365.

The result: minimal cash handling and risk, better accuracy and tracking — and of course, fewer bank runs.

However, digitizing payouts often results in some leftover cash in the drawer. Over time, we’ve heard from customers who prefer to use up that cash to pay out tips, then distribute the remaining tip amounts via Kickfin.

With Blended Payouts, you can do just that — and still account for every penny paid out, quickly and accurately, within the Kickfin platform.

How Blended Payouts Work

As always, all Kickfin customers can still choose to split individual payment amounts between instant payouts and payroll. Once you enable the new Cash Payouts feature, you will now be able to account for any cash tip payments that were also distributed.

Note: This feature lives within Kickfin’s Tip Calculator, which means you must have an active POS integration to use it.

Once it’s enabled, you’ll see the new “Cash Payouts” button on the Payment Review screen.
After clicking the button, users will be able to enter the individual cash amounts that were distributed to employees.
Back on the Review screen, you’ll see instant payout, payroll, and cash payment amounts for each employee. All three payment methods will have their own line items and be accounted for under your Payment Details.

Watch here for a full walkthrough of the new feature.

Ready to enable Blended Payouts?

If you’re a current customer, in touch with our Customer Success team at support@kickfin.com to activate this new feature.

(Not a customer yet? Click here to see Kickfin in action and learn how you can automate tip pooling and payouts!)