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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For restaurant owners looking to boost teamwork and make sure every employee gets their fair share, a tip pool or tip share seems like a natural solution. But like there are pros and cons to tip pooling that every operator should be aware of.

Of course, it doesn’t always make sense to pool tips. (And when it does make sense, tip pooling policies are definitely not one-size-fits-all!) 

If you’re on the fence, check out our tip pooling pro-con list below and consider how they would affect your restaurant’s unique dynamics. 

What are the pros of tip pooling? 

It takes a lot of hard work and collaboration to deliver an excellent guest experience. For most restaurants, the primary goal of tip pooling is to ensure all employees are fairly rewarded for their contributions.

Here are a few of the benefits that tip pooling offers restaurant teams.

1. Improved performance 

When executed strategically, tip pooling can bring your team together around a shared goal — delivering a top-notch guest experience — and reward them for doing so.

And when employees are all working toward a common goal, they’re much more likely to work together and go out of their way to lend a helping hand or fill in gaps. This can be particularly true for tip pools that include employees who generally aren’t directly tipped, like bussers, hosts, and back-of-house employees. 

2. Reduced competition among servers

Does one section get all of the large parties (aka all the large tips)? Or does your patio section get too hot for most guests during the summer? When employees aren’t sharing tips, your workplace culture might start to feel (overly) competitive and even lead to tension or disputes. When servers start feeling slighted or get hung up on who-got-which-table, not only does that affect morale — it slows everyone down.

An equitable tip pool can keep servers from feeling like they need to keep score, so they can focus on providing top-notch service to all of the guests in the restaurant. 

3. Increased focus on training

When you bring on new staff, you typically have them train with your best veteran servers. And when those vets know that their trainee will be part of their future tip pool, they’ll be more invested in the training, making sure to give them a master class in upselling and customer service. 

4. More equitable distribution 

Unfortunately, customer biases — conscious or not — can impact tip amounts. Whether based on race, gender, or other factors, this kind of discrimination can affect your employees’ livelihoods.

While restaurant operators can’t control if some employees receive preferential treatment, they can help to compensate for those injustices by pooling and fairly distributing tips.

Cons of Tip Pooling 

While most restaurants these days run some form of tip pool or tip share, there are some common drawback and pitfalls to tip pooling, which are worth considering before you implement a new policy

1. Top performers may feel negatively impacted

If your best servers are consistently bringing in far more than the standard 18-20% in tips, they might not be so pleased to share with employees who may not have the same experience, talent or work ethic.

Couple that with the fact that some servers can turn tables much quicker than others, resulting in a higher volume of sales and a whole lot more tip income — well, your top earners could start feeling cheated by the tip pool. 

And in a tough labor market, if a hardworking employee isn’t happy with their earnings, they likely have other options.

2. Under-performers can slip through the cracks

On the flip side of that: a tip pool could allow lower-performing employees to slip through the cracks. If you’re not closely evaluating the average tip amount (and average check size!), you may miss that one of your employees is struggling with their customer service. 

3. Compliance is an added consideration

Tip pooling is regulated at the federal and (usually) state level. Some municipalities also have their own rules around how to legally pool tips. These laws can get pretty complicated, making it all too easy to fall out of compliance without even knowing it. For example: managers can’t participate in a tip pool; but what happens if a manager is also performing server duties? Can you include back-of-house in your tip pool? Does your eligibility for the tip credit change if you operate a tip pool? It’s important to know the answers to all of these questions and fully understand the laws that apply to each of your locations. (Especially if you have locations in multiple states!)

Tip Pooling Pros and Cons at a Glance 

That’s a lot of information to take in, so here it is a handy-dandy pro-con chart.

To Pool or Not to Pool?

The majority of restaurants in the U.S. operate some form of tip pool. At Kickfin, we’ve worked with thousands of restaurant teams who participate in tip pooling or tip sharing. We’ve found that often, the positives outweigh the negatives. 

But that comes with a major caveat: the best tip pooling teams have been strategic and intentional with their policies — and as a result, no two tip pooling policies look exactly the same.

If you want to set yourself up for tip pooling success, here are a few general rules of thumb.

  1. Evaluate your requirements: Ask yourself why you’re running a tip pool. What needs are you trying to address or problems are you trying to fix? Specifically consider your restaurant type, team size, org chart, and local market to find the best policy for you.
  2.  Don’t overcomplicate: It shouldn’t require a degree in calculus to calculate your tip pool. If you feel like it’s getting unwieldy, it’s possible you’re setting your team up for mistakes and tracking issues.
  3. Get feedback for better buy-in: This shouldn’t be a decision-by-committee scenario, but it’s worth checking with management and even some of your team’s unofficial leaders to get their input before running with a new policy. This can help get the rest of your employees on board.
  4. Write it down and run it by your counsel: Your tip pooling policy should be on paper, in black and white. You should also have your legal counsel review it to make sure you’re not inadvertently out of compliance with tip pooling regulations. 
  5. Communicate everything: Once you’re feeling good about your policy, share it. Make sure every tip-eligible employee understands how it works and has the opportunity to ask questions.
  6. Ensure transparency by tracking everything: It’s not enough to share your policy. It’s important that every payout is tracked, including how those payouts were calculated. Not only does that streamline accounting and reporting; it also creates a culture of trust with your employees. If there is ever any question around a payout, having a digital paper trail is invaluable. 

The best tip pools are automated 

Tip pool calculations often happen in a spreadsheet, which is less than ideal. Kickfin integrates with your POS, so you can eliminate spreadsheet math, reducing the risk of human error and ensuring every payout is accurately calculated and tracked. Plus: Kickfin customers can send instant, cashless payouts directly to their employees’ bank of choice.

The result: All the benefits of tip pooling, without the hassles, risk, and time required. (In fact, many of our users can calculate and pay out tips at the end of each shift in under 60 seconds!)

Want to learn more? Request a demo today. 

 

 

Kickfin has earned a top spot on the 2025 Inc. Regionals list in the Southwest region! This recognition places us among the fastest-growing privately held companies in America—and we couldn’t be prouder of what this means for our team, our customers, and the restaurant industry at large.

A Milestone Achievement

As the #1 tip distribution platform, Kickfin is trusted by thousands of restaurant teams to automate tip pooling and payouts. Since 2017, our technology has given managers hours back in their week while improving accuracy, visibility, and reporting for operators. 

Only 951 companies made the cut across all regions, and in the Southwest alone, the businesses on this list contributed 13,809 jobs to the U.S. economy while achieving a median growth rate of approximately 106 percent from 2021 to 2023. 

Powering the Future of Tip Management

In the past year, Kickfin has taken automated tip management to a whole new level. In addition to exciting new features that make our platform more robust than ever, we continue to add to the list of our direct integrations with the leading POS brands—which currently includes Toast, SkyTab, Square, Heartland, RPOWER, PAR POS, Oracle MICROS, NCR Aloha, and more.

→ See how the Kickfin-Toast integration “changed everything” for HOBNOB restaurants

Kickfin’s POS integrations give our customers the ability to auto-calculate even the most complex tip pools in just a few clicks, which eliminates unwieldy tip spreadsheets, saves managers even more time, and gives operators unprecedented visibility into payout calculations and history.

A Heartfelt Thank You

This achievement wouldn’t have been possible without the trust of our customers and the dedication of our team.

As Justin Roberts, co-CEO of Kickfin, puts it: “We’re incredibly grateful to our customers who have made this growth possible by trusting Kickfin with their tip management needs. This recognition is a testament to the value that automated tip management brings to restaurant teams—helping them save time, reduce risk, and take care of their people.”

We’re honored to be included in the 2025 Inc. Regionals list, and we’re excited to see what the rest of 2025 has in store!

You heard that right — Kickfin has added yet another partner to our ever-growing list of POS integrations!

RPOWER POS has joined the list of leading POS systems that now integrate with Kickfin so users can fully automate tip calculations and payouts. 

RPOWER is a trusted name in the restaurant industry known for its handheld devices, online ordering capabilities, and robust reporting. RPOWER’s dedication to staying on the cutting edge of restaurant tech makes the integration with Kickfin a perfect match! 

With the RPOWER-Kickfin integration, restaurant operators can: 

  • Easily build out highly complex tip policies 
  • Calculate tip outs based on roles, shifts and hours worked
  • Distribute tips directly to employee bank accounts 
  • Establish an electronic “paper trail” for every tip out

( …and more. Dive into the latest Kickfin updates for the full scoop.)

Like all of our integration customers, when RPOWER users activate the Kickfin integration, they’ll have access to our robust Customer Success team (at no extra cost!). We’re here 24/7 to review and build out your tip policy within the platform, so you’ll be up and running in a flash.

Collaboration with Riot Hospitality Group

This integration was especially exciting because we worked hand-in-hand with one of our longstanding customers, Riot Hospitality Group, to ensure the integration checked every box — and that it could handle their complex tip pooling policies. 

“Kickfin has been an outstanding partner to Riot Hospitality Group for years,” said J Goldin, the systems director for RHG. 

“They had already helped us go fully cashless, which eliminated a lot of risk for our teams. When we decided to completely automate tip payouts, they were a natural choice to help with that as well. We worked hand in hand with Kickfin and RPOWER to ensure the system could handle the intense complexity of our rules, while still being incredibly easy to use for our operators.”

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“Kickfin is easy to implement and easy to use. If you’re thinking about trying it, you’ll be glad you did.”

As our co-CEO Justin Roberts puts it, this integration is a “no brainer for RPOWER users who understand how valuable their managers’ time is.”

RPOWER users, we’re ready for you! Schedule a demo to learn how you can activate your integration. 

(Not an RPOWER user but want to take advantage of these time-saving features? See if Kickfin is integrated with your POS!) 

We kicked off 2025 with some major (!) updates to our Tip Calculator features.

It was a big release, and we’ll break it all down for you here — but the big headlines are:

  • More integrations
  • More speed
  • More flexibility

If you’re not already using Kickfin — or if you haven’t integrated Kickfin with your POS to automate tip calcs just yet — this is for you! Read on to see how you can use Kickfin’s newest tip calc features to un-clunk your tip pooling process. 

More integrations, coming right up

We’re continuing to roll out integrations with the leading POS systems, giving restaurant teams the power to auto-calculate tip pools and shares in a matter of clicks. 

(Side note: Kickfin only builds direct POS integrations — not using a third-party solution! — which streamlines your tech stack and keeps your costs lower.)

We were thrilled to add RPOWER to our growing list of integrations, which already includes Toast, Square, SkyTab, SpotOn, PAR and more.

If you’re an RPOWER user and you’re not yet a Kickfin customer, request a demo and we’ll show you the integration in action!

Handle autograts with ease

For servers and bartenders handling large parties, autograts can be great — but for managers, they can turn into a logistical nightmare. Now, Kickfin can help with that…

With this latest release, you can break tips and autograts into separate categories with their own set of rules for distribution. You have the flexibility to manage autograt tip splits completely separate from regular tip outs, so you can fairly reward a hardworking server-bartender-busser trio for a job well done on a 30-top.

Tips & Autograts Broken Out on Tip Data Page

Tips & Autograts Broken Out on Review Screen

With this new set up, you’ll also get more transparency in reporting. You’ll be able to see the breakdown of tips and autograts collected by each user in your reporting dashboards (more on that later!).

Include cash tips in your distributions 

You heard that right — we can now distribute shares of cash tips digitally, directly to your employees’ bank accounts. Instead of doing the math on cash tips by hand, you can easily add cash to your tip pool, and we’ll calculate the share among employees for you. 

Important note: cash distributions aren’t available for all of our integration partners. Contact us for more info. 

Advanced Tip Rules (for even the unruliest policies)

Think your tip policy is extra tricky? Don’t worry — we’ve seen ‘em all. And there aren’t many Kickfin can’t handle, thanks to our Advanced Tip Rules feature.

If you have Advanced Tip Rules enabled, we’ve added a few new capabilities so you can further customize your tip share while we take care of the complicated math behind the scenes. Here are just a few examples of the new features we’re rolling out. 

Not using Advanced Tip Rules? Reach out to us if you’d like to enable these features. 

Per Segment Tip Sharing

We’ve been calculating tip shares on a check-by-check basis. For example, if you have servers sharing a percentage of tips with bussers, we would only calculate and deduct that percentage if a busser was working at the time that a check was processed. We call this Per Check Tip Sharing

Now, we’re introducing Per Segment Tip Sharing, which gives you the option to deduct a tip share from every check processed during a shift. Let’s go back to our example — servers sharing a percent of tips with bussers. With Per Segment Tip Sharing, we would deduct a percentage of the server’s tip for every check processed, even if the busser gets cut two hours before the server. 

Split Evenly 

Would you prefer that all of your support staff take home an even share of their tip pool? We can now make that happen.

Previously, our tip shares entered a pool and were divided among beneficiaries based on how many minutes they worked during a shift, which we call splitting by Time Worked. With our new product update, we’re introducing the Split Evenly option, which enables you to send an equal part of a tip share to every beneficiary that worked within a segment. 

More accuracy 

In the past, cash autograt payments were lumped in with credit card autograts and credit card tips, resulting in credit card fee deductions on cash transactions. But that is no more! 

Now we’re able to deduct credit card fees only where they apply, so you’ll no longer see credit card fee deductions attached to cash autograt transactions. 

Plus, we’ve gotten even better at math. With our new update, we can prevent rounding errors, so our tip disbursal should match the tips collected in your POS to the penny. 

Revamped and expanded reporting 

We added new reporting views to give you more insight into each pay period, individual pay sets, and tip calculations. Here’s a quick look at your new pay period report with expanded filters:

Main Pay Period Report - Filter Bar Expanded

You’ll notice that there are now separate columns for tips and autograts, but you can still view the gross amount earned (tips + autograts = gross).  

And it doesn’t stop at the main reporting page. You’ll see this more detailed reporting when you look at individual employee pay period reports, review a specific pay set, or export the information from any of your reporting dashboards. 

We know this is a lot of new information to take in — but we’ve got you covered with our full Product Release Recap. Simply log in to Kickfin, click on your name in the upper left corner and select “Support” to access that portal. 

Not using Kickfin? Dying to get rid of your old-fashioned gratuity management system? Drooling over these new features? We’d love to have you. Reach out to us today to see how our platform could save you time and money.

See Kickfin in action!