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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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.

Do you start getting heart palpitations when you see a large party reservation in your section? This one’s for you.

Maybe your restaurant is a local go-to for corporate dinners, milestone celebrations, and birthday parties…or maybe you regularly get blindsided with 20-top walk-ins when you least expect it. 

As every hospitality pro knows, no matter how prepared you are, managing large parties can be tricky. But if you do it right, it can be a fast track to large tips. 

So the next time a 20-top bachelorette party drops in and “forgot to make a reservation:” no need to hyperventilate! We’ve got the tips and tricks that can keep you sane throughout a large party — and hopefully help you reel in a well-deserved tip. 

4 Tips for Staying Organized 

When your 25+ top walks in, getting overwhelmed can lead you to drop the ball on service and hospitality because, hey — you’re just trying to get right right food, to the right person, as fast as possible. But your guests can pick up on when you’re frazzled or frustrated, which can impact their experience (as well as your tip).  

Here are a few ways to stay organized and calm throughout service.

1. Get (a little more) familiar with your POS

Every POS system is different, but most have come quite a long way in terms of features and flexibility. There are likely bells and whistles on your POS that you might not use every day, but that can make managing large parties much more seamless.

So use all that tech to your advantage. Set aside time for some extra training or research to understand what your POS is capable of, so that it’s all muscle memory the next time you have a large group sitting in your section. 

For example, here are just a few things you should know about your POS as it relates specifically to large parties:

  • Is there a max number of ways you can split a bill evenly? 
  • How many checks can you create on each table? 
  • How many ways can you split a single item? 
  • Do you need manager permission to add auto-gratuity? 

2. Assign seat numbers

The only way to stay sane when dealing with a large party is to assign seat numbers — and stick to them. 

You should assign seat numbers starting with your first guest on the left and continue around the table moving counterclockwise. As you put in the first round of drink orders, your POS should allow you to assign items to a seat number. Even if guests move to different seats throughout the meal, stick to their original seat number. 

Sure, it’s tedious — but these numbers will be your saving grace when someone asks you for another drink or when they want to split the check by family. No matter how in the weeds you are, take the time to add seat numbers. You’ll thank us later.

When they ask for 15 separate bills, you can just drop each seat number into a new check and print. No need to go back and ask, “who had the fish?”

3. Don’t trust your own memory 

As a server, it’s normally a crowd-pleasing flex to take everyone’s order from memory. But when you’ve got 17 people depending on you to make grandma’s 97th birthday lunch a success: Pull out your server book

Not only are you bound to forget something, but your guests may not feel entirely comfortable either. If they’re worried you’re going to forget they want their sauce on the side, they may be less inclined to ask questions about specials or which dishes are your favorites. And if guests feel like they have to stick to the basics, you’re missing out on all of your upselling opportunities. 

Just for the night, don’t be a hero: write down everyone’s order!

4. Bring in some help 

Depending on how many guests you have at one table, you might need more help than normal — and there’s no shame in that.

If you’re aware that a big party is on the books, coordinate with your team ahead of time. For example, see if you can have an assigned busser or bartender on call to help you keep drinks filled, tables clean, and guests happy.

Wowing Your Guests 

To secure the huge tips that come with large parties, you’ll have to go above and beyond. 

  • Be ready to make suggestions. Being knowledgeable about the menu always reflects well. Explain your specials in detail, offer drink pairings, and accommodate guests with special requests. This is your shot to upsell and increase the bill! 
  • Keep the drinks flowing. No one wants an empty glass. Send bussers around with pitchers to top off waters, and always be ready to grab another round of cocktails. 
  • Stay in contact with the kitchen. Give the chefs a heads up that you’re going to put in a large order so they can prepare accordingly. With more preparation, they’ll be able to get the whole table’s food out in a timely manner. No long waits for everyone to receive their food! 
  • Pre-bus as much as possible. Keep the table neat and tidy, so they have rooms for multiple rounds of appetizers, drinks, and dessert. 
  • Use your seat numbers. You shouldn’t have to serve entrees as if it’s an auction. Instead of announcing each dish to ask, “who had the burger?” you should be able to reference their seat number and pass each entree to the right guest. It’s a simple way to show your serving prowess (and speed up the serving process!). 

Even with a crowd at your table, you can go above and beyond on service. Your guests will take notice and show their gratitude on the tip line (more on that later).

Splitting the Bill

You’ve made it through most of the craziness of a large party — but now it’s time to settle the bill. Before everyone closes out their tabs, you might have to navigate a few sticky situations. 

Who’s paying? 

It’s always awkward to stand next to the table while people fight over who’s taking care of the bill. Here’s what you can do to alleviate some tension:

  • If someone offers to pay early on in the meal, take them up on it. Go ahead and keep their card so you can run it before the arguments start. 
  • When 3 different people want to pay for the meal, offer to split the bill evenly. They probably won’t take you up on it, but your suggestion should get one of the parties to acquiesce. 
  • Ask how checks will be split at the beginning of the meal to avoid the awkward card dance at the end. You’ll also have an easier time splitting items if you know ahead of time! 

To auto-grat or not to auto-grat

Do you want to make sure you get your full 20% tip after a big table runs you ragged? Or would you rather take the risk in hopes that you’ll get an even bigger tip? 

If your restaurant has an auto-gratuity policy for large parties, some servers prefer to take the sure thing and hope that your guests feel inclined to give you an extra thanks on top of it. Most guests aren’t offended and even appreciate that they don’t have to do any math — but make sure that they’re expecting the service charge. A simple line like, “We have already included a 20% gratuity in accordance with our large party policy,” goes a long way. 

When you have a really fun rapport with a table, it might be the right time to forgo the auto-grat and let your guests decide how much they’d like to thank you. Keep your guests in the know, too! Some may assume that you included gratuity and skip the tip line altogether. 

Either way, steel yourself before you look at their final bill. You might be surprised when customers leave less than you expected, or you might be treated to a heavier-than-average tip. 

Tipping out 

After it’s all said and done, your manager may have a tip out policy for supporting bussers and bartenders who assist with large parties. Make sure you know what to expect to take home after tipping out your team. 

And managers, Kickfin makes large party tip outs easy. Make sure that your event bartender gets their fair share of server tip outs, without spending hours with your calculator. 

>>Learn more about Kickfin’s newest tip calculation features

Whether you’re hosting a graduation party or taking care of a corporate holiday dinner, be ready to handle it with the same care and attention you give to a two-top — and let the big tips roll in! 

We’re thrilled to announce that Kickfin made the Deloitte Technology Fast 500™ list, a ranking of the 500 fastest-growing technology, media, telecommunications, life sciences, fintech, and energy tech companies in North America.

How Kickfin stacks up

Overall, 2024 Technology Fast 500 companies achieved revenue growth ranging from 201% to 153,625% over the three-year time frame, with an average growth rate of 1,981% and median growth rate of 460%.

Our 2,144% revenue growth earned us the 65th spot on Deloitte’s list. It’s another exciting milestone for Kickfin — but more importantly, it’s a meaningful validation of our mission to take the clunk out of tip management, so payouts are faster, smarter and safer for every restaurant team we serve. 

Based on Deloitte’s ranking, Kickfin is:

  • The highest-ranked restaurant tech company on the list
  • The *only* tip management company on the list
  • Austin’s fastest-growing tech company

Growth driven by product innovation, demand for automation

Kickfin was the first digital end-to-end tip management solution on the market — and with more than $2 billion payouts to more than 250,000 restaurant employees, we continue to be the largest and top-ranked.

Why?

It comes down to working the way our customers work — and not the other way around. Not only do we automate the tip pooling and payout process for thousands of restaurants and bars; no two tip policies are alike, so we’ve built a solution that gives them the flexibility and customization they require.

With more than $2 billion payouts to more than 250,000 restaurant employees, Kickfin continues to be the largest and top-ranked tip management software on the market.

That’s a big reason we’ve focused on building direct, robust integrations with the leading POS systems on the market. So far, we’ve rolled out integrations with Toast, SkyTab, Oracle, PAR, Heartland and Square — and the list continues to grow.

“In recent years, digital tip management has become table stakes,” said Justin Roberts, Kickfin’s co-founder and co-CEO. 

“Operators now understand the significant efficiencies to be gained by eliminating manual tip-out processes. It’s no longer a question of ‘if,’ but ‘how.’ As a direct result of our commitment to innovation and customer success, we’re thrilled to see more and more restaurants select Kickfin to modernize their tip management.”

A big thank-you to our customers who trust us with their payouts, to our partners who support, collaborate (and integrate!) with us, and of course, every member of the Kickfin team.

About the Deloitte 500

Now in its 30th year, the Deloitte Technology Fast 500 provides a ranking of the fastest-growing

technology, media, telecommunications, life sciences, fintech, and energy tech companies — both public and private — in North America. Technology Fast 500 award winners are selected based on percentage fiscal year revenue growth from 2020 to 2023.

In order to be eligible for Technology Fast 500 recognition, companies must own proprietary intellectual property or technology that is sold to customers in products that contribute to a majority of the company’s operating revenues. Companies must have base-year operating revenues of at least US$50,000, and current-year operating revenues of at least US$5 million. 

Additionally, companies must be in business for a minimum of four years and be headquartered within North America. 

Ready to take the next step?

See how brands like Walk-On’s, Marco’s, Bar Louie and more are automating tip pooling and payouts with Kickfin. Schedule your 10-minute demo today

It’s an election year, in case you haven’t heard! 😉 This one has major implications for tipped employees — specifically, when it comes to taxes.

It’s no secret that our Democratic and Republican candidates are running on very different platforms. But when it comes to tip regulations, Vice President Kamala Harris and Former President Donald Trump actually both support reducing taxes on tips

A little context on taxes and tips

We’re just going to state the obvious: For the average American, tax reporting can be pretty, pretty confusing. For the millions of employees working in tipped occupations — well, that creates another layer of uncertainties.

(Do I have to report my tips? Do have to report my cash tips? Will anyone know if I don’t report my tips? What happens if I don’t accurately or fully report what I earned?)

Historically, there’s been a trend of hospitality employees underreporting cash tips to prevent higher tax burdens. And while this may reduce what employees owe Uncle Sam in the moment, there can be downsides: e.g., if they find themselves eligible for unemployment, if they’re trying to qualify for an auto loan or mortgage, etc.

However, that urge to underreport could be relieved in the near future, given the tax code changes both of our presidential candidates have proposed. The TL;DR: Both Trump and Harris have voiced their intention to relieve some of the burden on tipped workers in restaurants, bars, hotels, and other service positions. 

Here’s a quick summary of each candidate’s plan, as well as some potential impacts for restaurant employees. 

Trump’s plan for tipped employees 

Trump shared his plan to reduce tipped income tax burden at a rally in Las Vegas — fitting for a city that’s built on the gig economy. Nevada is home to the highest concentration of tipped employees who work in the many hotels, casinos, and restaurants that millions of tourists flock to annually. 

During the rally, the former president announced that he would make tipped income exempt from federal income tax, stating it would happen “right away” when he takes office. 

Since speaking at the rally, Trump has not yet clarified what this would mean for tipped employees. Many servers want to know if this is an exemption just on federal income tax or if the proposal includes payroll taxes (social security and Medicare). 

Harris’s tip tax proposal 

Harris also took the opportunity to speak on her tipped income policy while visiting Nevada. Much like Trump, she knew she’d have a captive audience when it comes to tipped earnings. 

Her proposal promises to exempt tipped income from the federal income tax, but she has made clear that tips will still be subject to payroll taxes. While not yet confirmed, campaign insiders say Harris is considering placing some guardrails on her plan — like a caveat that the tax exemption only applies to employees earning less than $75,000 per year. 

Is one plan better than the other? 

In short: probably not. (Most service and hospitality workers do not earn above the $75,000 threshold that’s been suggested by the Harris campaign.) So either way, servers, bartenders, and hospitality staff can expect to see a lower tax burden during the next administration. 

But what does that look like in practice? 

Most tipped employees aren’t receiving their tips on payroll — they’re walking out of every shift with their earnings for the night, deduction-free. Instead, the taxes are paid on payroll out of their hourly earnings, which is why many servers get $0 paychecks every two weeks. With a reduced tax burden, most servers will see the difference in higher paychecks.

On the other hand, economists are wary of the impact of eliminating taxes on tips, citing the reduced funding for social security and Medicare. And with so much negative sentiment around “tipflation” these days, experts also speculate that a reduced tax burden may result in even more hesitance at the tip screen. 

Increasing minimum wage 

We’re closely following campaign promises about an increase to the minimum wage — especially in regards to the tipped minimum wage and the tip credit

Minimum wage earners have been eyeing an increase, noting that the federal minimum wage of $7.25 per hour hasn’t increased since 2009, and servers, bartenders, and other tipped employees have been earning $2.13 per hour for over 30 years. An increased minimum wage paired with the reduced tax burden could make a major difference for service workers trying to keep up with the rising cost of living. 

In the Harris camp, removing tax on tips is just part of the plan to take some pressure off service workers. While Harris hasn’t shared a detailed plan for bumping up the minimum wage, she has indicated that she would support an increase

In previous election cycles, Trump stated that he would consider a minimum wage increase, but he has not shared his opinion on the matter during the 2024 presidential campaign. 

Of course, we’re a ways out from any real policy changes actually shape — but if you’re looking to make your tip management process less taxing in the interim (see what we did there?), Kickfin is here for you! Check out how you can use Kickfin to auto-calculate tip pools and send payouts directly to employees’ bank accounts in seconds.

See Kickfin in action!