Balancing Tech and Culture with Wil Brawley of Schedulefly

How can tech work within an employee-first restaurant culture? Ask Wil Brawley. 

As co-owner and co-founder of Schedulefly, a simple scheduling and communications tool for restaurants, Wil Brawley recognizes the value tech can deliver to restaurants. If you’re not familiar, here’s a quick overview of his platform:

Through his Restaurant Owners Uncorked podcast, Wil keeps his finger on the pulse of the restaurant industry, and he’s keenly aware of how tech can both improve and disrupt the employee experience. We sat down with Wil for some real talk on the upsides and downsides of restaurant tech and how restaurant owners can innovate without taking away from an authentic, human-centered culture.  

How important is the employee culture at a restaurant? Can it affect sales and daily operations? 

I’ve done over 450 episodes of our podcast, Restaurant Owners Uncorked, and worked on two books featuring successful restaurant owners, so I’ve probably interviewed close to a thousand restaurant owners in the past 15 years. 

If there’s one common thread across all those with long-lasting success, it’s culture. That culture might vary from place to place, but it is always centered on caring deeply about the people that work in your restaurants. The employees tend to come first, creating a culture that’s about nurturing and loving the people that work in the restaurant.

When your employees are well taken care of, they treat their customers well too, and then the investors do well, too. That’s been my observation.

How do you define a positive employee culture? What are the steps owners need to take to create that culture? 

For a long time, restaurant culture has been: “If you aren’t willing to work seven days in a row, then we don’t want you here. We want people that are going to show up and bust their ass.” And that’s changed for the better, for everybody. It’s leading to less burnout. It’s leading to less negative behavior outside of work. Substance abuse has been a big issue, and the industry is going through a conversation about mental health and substance abuse.

Yesterday, I interviewed someone for the podcast who started her first restaurant in Denver a couple of years ago. She’s worked in restaurants for 15 years and has worked in places where she actually worked 13 days in a row. Obviously that restaurant doesn’t have a great culture. You’d never have somebody work 13 days in a row if your employees came first. 

She learned from that, and now at her own restaurant, she never schedules anyone for more than four days in a week because she cares very deeply about the mental health and the well-being and the work-life balance of her employees. She knows that if she gives them what they need, then everything else is going to fall into place.

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“When you’re on day 12 of 13 days in a row, are you going to represent that restaurant and that brand well? Of course you’re not. On the flip side, an employee who feels their needs are being met and their work-life balance is respected will actually enjoy what they do and pass on that good, memorable experience to customers.”

With happy customers returning to the restaurant for reliably excellent service, the restaurant thrives and therefore so do owners and investors. 

How can tech be a positive part of your culture? And how can it cause tension? 

It’s quite a balance. There are 300+ restaurant tech companies out there right now, Schedulefly being one of them. People who use our platform tend to manage their folks and their behavior more through engagement and culture than by leaning on technology. What you’re really looking for is technology that will improve on the culture, not enforce it. 

Here’s a specific example. When you schedule someone for 10 am, they’re supposed to be there at 10 am, but you start seeing people clocking in five or 10 minutes early — which costs you money. You’ve created this schedule with a specific budget in mind, and when multiple people add just a few extra minutes a day, it runs through your budget much faster than you planned. 

You have two options to deal with the problem. One is to simply implement tech that systematically prevents people from clocking in early. The other, which I recommend, is building a culture where you can communicate openly with employees. You set the expectation, explain why it’s important, and create trust that everyone will do their part. 

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There’s nothing wrong with using tech, but it creates a different type of culture where you expect tools to influence behavior versus communication. “

You run into similar situations with Schedulefly. If someone offers up a shift and another employee wants it, the manager has to make a decision: is that the right person to pick up that shift?

If it’s not the right person, they’re not going to allow that trade, and then they’ll need to talk to the person to say, “I appreciate that you’re trying to pick up this shift. This is a prime shift and we need one of our veteran servers to pick that shift up. You aren’t quite ready to handle that yet.” It creates an opportunity for engagement. Again, that’s part of a culture of engagement and trust. 

Yeah, it’s easier to use technology than to have these interactions, but to have a robust, thriving, healthy culture, you have to communicate. We really encourage people to use technology where it helps, but it can’t replace engagement and human interaction. 

Do you find that it’s harder to build this culture in larger chain restaurants?

Communication isn’t just for smaller restaurants with only one or two locations. Some people believe that as you grow, you have to become more “corporate” and use lots of technology, but you find that the culture becomes less friendly, less human-oriented. People who loved working there when it was fun and authentic will probably leave for the place down the street that can provide that.  

Big Red F in Boulder, Colorado has 800 employees across over 16 locations, and to this day, culture is king there. They really figured out culture at scale, so it’s definitely possible. They’ve been a customer of ours for 14 of our 16 years at Schedulefly, so I’ve studied them for a long time. They certainly have one of the best cultures I’ve come across. It’s been interesting to see them grow this much without losing their truly authentic, employee-focused culture. 

What should restaurant owners take into consideration when exploring new technology options? 

Some people want a comprehensive, one-size-fits-all solution that manages everything, and there’s certainly a place for that, but I think sometimes you wind up spending as much time managing the technology as you are managing your people. And that’s just a question you have to ask: Which is more important?

You definitely want to consider implementation. Is this something that takes a lot of training and focus, or is it easy-to-use, point-and-click to get started?

Support is another big one that I think may get overlooked sometimes. This tech company may have a great slick software, but do they have great support to back it up? Because your employees have questions, and you’re going to have questions.There will always be problems, like small glitches, so you should find out if the tech company you’re interested in is known for outstanding customer service. 

Finally, you need to marry the need with the priority and timing. We see people sign up for a 30-day free trial of Schedulefly, never use it, and then start the trial again six months later — only to not use it again. Eventually, they do implement and move forward. Talking to people over the years about this, I found that it’s a matter of just prioritizing. Running a restaurant, you’ve always got a long list of things you have to manage, so you have to be able to prioritize and hit the most important one first. So, be realistic about your own time management and top priorities before trying to implement new tech. 

Any final words of wisdom for restaurant owners making decisions about their tech stack? 

With 300+ restaurant tech platforms out there right now, every one of them is hoping to earn your business. It must be overwhelming to sift through all that noise to find the tools that you need.

Start with a focus on employees and trying to give them what they need and deserve to be successful — and again, you want to balance that with not bringing so many tools that there’s no engagement and management. 

As you prioritize which problems you need to resolve within your business, I always encourage people to remember good old-fashioned word of mouth. Call people you know in the industry and find out what they’re using. Ask if it’s solving their problems and if it’s backed by phenomenal customer service. 

And if you’re talking to a salesperson, ask them for a list of their customers in your area and start talking to them. That’s probably one of the most efficient ways to figure out what if a tool will be useful and will contribute to your success in the long run.

Learn more about Schedulefly or catch the latest episode of ROU.

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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!

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!

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!)

Kickfin is excited to share the latest addition to our integration marketplace. Read on for all the details around our partnership with Union POS. (If you’re a current Union POS customer and you’d like to learn more about how Kickfin automates tip pooling and payouts, schedule a live demo here.)

AUSTIN, Texas (August 13, 2025)—Kickfin, the leading tip management software, today announced the launch of its integration with Union, the purpose-built POS and engagement platform powering the nation’s busiest bars, nightclubs and restaurants.

Thousands of operators use Kickfin to eliminate tedious tip calculations and remove cash from the tip distribution process so managers can move faster, track everything, and ensure accuracy and compliance.

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By activating the Kickfin-Union integration, we eliminated clunky spreadsheet formulas and fully automated our tip pooling process. After going live, we reduced our time to close out by an average of 30 minutes after every shift.

The Kickfin-Union integration gives Union’s customers the power to auto-calculate tip pools in a matter of clicks and send payouts directly to employees’ bank of choice—no cash or pay cards required.

“By integrating with Kickfin, we’re giving operators the power to choose best-in-class tools that work seamlessly with their Union POS and data,” said Alex Broeker, the CEO and founder of Union. “This direct integration brings automated tip management to our operators while unlocking new opportunities for operational efficiency, employee satisfaction and simplified compliance.”

KPG Hospitality, which operates experiential bars and unique concepts throughout Texas and Tennessee, was among the first operators to activate the Kickfin-Union POS integration.

“Our venues run at a very fast pace. When you consider the time it takes managers to manually calculate tip amounts every day, after every shift, across every location, it’s a lot of unnecessary admin hours,” said Troy Cramer, the managing partner at KPG. “By activating the Kickfin-Union integration, we eliminated clunky spreadsheet formulas and fully automated our tip pooling process. After going live, we reduced our time to close out by an average of 30 minutes after every shift.”Key Features of the Union + Kickfin Integration:

  • Automated Tip Pool Calculations: Calculate complex tip pools in seconds, saving managers hours of administrative work while ensuring accuracy and transparency.
  • Instant Cashless Payouts: Pay out tips directly to employees’ bank of choice instantly, eliminating the need for cash handling and bank runs.
  • Simplified Compliance: Maintain a digital record of every payout, making tip reporting and tax compliance straightforward.
  • Enhanced Tracking: Easily track tips by pay period with comprehensive reporting capabilities.
  • Streamlined Operations: Implement complex tip policies with just a few clicks through an extremely easy-to-use interface.

“Our integration with Union, a leading POS system built specifically to support the busiest venues in the industry, makes perfect sense,” said Kickfin co-CEO Brian Hassan. “Together, we’re creating a solution that saves time, reduces errors, and delivers a better experience for both operators and their staff.”

Available immediately through both Union and Kickfin, venues can integrate their systems and begin leveraging these capabilities today. To learn how this partnership can transform your tip management operations, schedule a demo at GetUnion.com or kickfin.com/demo.

About Union
Union powers a first-of-its-kind venue operating system purpose-built for the nation’s busiest bars and restaurants. More than a point-of-sale, Union connects 1,500+ establishments with 5M+ consumers and leading brands through real-time consumption data. The platform drives operational efficiency, enables frictionless mobile ordering, and facilitates brand-patron interactions that enhance venue loyalty. With $2B+ in annual transactions, Union creates a virtuous cycle where venues improve customer experiences, brands gain direct consumer engagement, and patrons enjoy personalized rewarding hospitality—transforming high-volume operations into next-gen guest experiences. To learn more about Union, visit http://www.getunion.com

About Kickfin
Kickfin is a leading digital tip management platform that automates tip pool calculations and delivers cashless tip payments directly to employees’ bank accounts. Designed to eliminate the administrative burden of tip management, Kickfin helps restaurants, bars, and hospitality venues save time, reduce errors, and improve employee satisfaction. With features like instant payments, digital record-keeping, and simplified compliance, Kickfin is transforming the way venues handle tip distribution in today’s increasingly cashless economy. 

See Kickfin in action!