Customer Loyalty, Part 2: My Experiences with Rewards Programs

Article originally written for and featured in Square’s Seller Community:

I own and run a small neighborhood Ice Cream shop, Pesso’s Ices & Ice Cream, in Bayside Queens. From our first day open, on November 5th, 2004, we decided we wanted to have a Loyalty & Rewards Program in order to help keep our customers excited about coming back.

At the time, our only viable option was the classic paper punch card. The 14-year-old me mocked up a simple design on Word, we bought a print-your-own business card kit, a pack of perforated thick printer paper that easily pops out individual business cards, and we made our first punch cards. Once this method took off and we saw that our customers liked the program, we upgraded to getting our cards professionally printed, and we special ordered some unique hole punchers so that they would be harder to counterfeit.

Positives of Punch Cards

Our customers really loved this program from the moment we launched it. It was simple enough, customers received 1 Punch for every item that they purchased, no matter the size, and received a free Small Cup when they completed the card.

These paper punch cards were also very easy enough to use. It only took a few seconds to punch up a card, without the need to sign up for anything, or share or enter any personal or contact information. This speed and anonymity was a great feature that made everyone feel safe and comfortable with the system, and feel like getting rewards was not a burden.

And while this method worked really well for many years, there were some downsides and we started having major issues. And these problems with paper punch cards definitely outweigh the positives.

Problems with Punch Cards

First of all, because they’re paper and anonymous, your business doesn’t end up with any data. You don’t know how many punch cards are out there, how many unique customers you have, how often they’re coming in, or anything else. The goal of a loyalty program is to keep people coming, but if you don’t have any data, then you can’t even tell if it’s actually working or not. This lack of data makes it really hard to tell if they’re just coming because of your product and service, or if your Loyalty Program is worth it and if it is contributing or not.

Another issue we had with our Paper Punch Card system was the constant designing and redesigning of our cards. We’re a very agile business, and we constantly make big changes to our business based on the data and sales trends of our customers that we get from using Square. Any time that we changed our product offerings to remove low performing and low profit product lines, we needed to change our rewards program to match it.

Over the years we increased the number of punches on a card, and changed the reward from a free Small to the Dollar Amount equivalent, so that our customers could redeem it for any item they wanted, and still get the same value.

With paper punch cards, this change took time to redesign the punch cards, order, and reprint them. Depending on when we made these changes, we also had to either finish up the cards that we had left, or to throw them out and lose money, before we could make a change to our product line.

The cost and effort of constantly ordering and printing new cards was also a factor. Because they were physical paper cards, they were easy to lose or to forget to bring in, or get ruined in the rain or laundry. Since we wanted as many customers as possible to use our program, we always offered every customer a new card if they didn’t have one with them, so we were constantly handing out more cards. We ended up printing at least 20,000 cards every single year, and the cost really added up.

The expensive custom hole punchers that we ordered were very effective at preventing counterfeiting, and were pretty high quality, but they still did break every couple of years, and the costs added up there too.

Program Lifespan

While the costs were an issue, the bigger issue was the integrity and lifespan of the program. By 2016, we started noticing that fewer and fewer people were bringing in their cards, and ever fewer wanted new ones. Because customers kept forgetting their cards, getting new ones, and ended up with piles and piles of cards, they were getting annoyed with the program.

While it was easy to combine cards, people were getting frustrated with having so many cards. On many occasions, we’ve had people coming in with 30 cards at one time to combine them. While we didn’t mind doing it, customers were getting tired of keeping track of their cards and stopped using them. This definitely took a toll on our customers and they didn’t even want new cards or to continue with the program. The cycle was ending.

A loyalty program that customers don’t use is a loyalty program that doesn’t work. A rewards program only works if people use it, and people will only use it if they are excited to use it. And people aren’t excited to use it if it’s a hassle. So we decided that it was time to rethink our program in order to simplify and digitize it, and make it exciting for our customers again.

Going Digital

We looked at the many different options out there, and we noticed that Square, the system we use for our Point of Sale and all other business management, had just revamped their Loyalty system, and it finally had the key features that we needed.

So we took a leap and jumped onto the Square Loyalty Program. Setting up the program was incredibly easy. We were able to use the same program structure, as our paper punch cards, so the only thing that changed was going from paper to digital.

This change instantly had huge positive impacts, including giving us the data we needed, simplifying the use of the Loyalty Program for our customers and employees, and reenergizing our customers’ excitement about Rewards.


As soon as we switched over from our paper punch cards to the Square Loyalty program, we immediately started letting our customers know all about it. We made some signs to hang around the store and around our Registers, we updated our Website with details about the program and the link for customers to sign up and check their point status, and all of the fine print.

But the biggest and most effective way of educating our customers was talking to them. Already offered every customer a paper punch card, so we did the same with the new Square Loyalty Program. We write out scripts for our employees on how we want them to talk to customers, so we worked in some language about Square Loyalty. Our employees ask every single customer if they have Rewards Points with us, and walk them through the process to sign up.

Luckily right on time, the Square Register came out which was a perfect solution for Square Loyalty. With the removable Customer facing display, customers can enter in their own numbers privately and accurately, as well as redeeming their own reward. This tremendously simplified the process of using a Rewards Program, sped up our lines, and made a better customer and employee experience.


Because we had 15 years of Paper Punch cards out in the world, transitioning over was definitely a process. Rather than attempting to try and convert over all of the paper punch card to Digital, which would involve a lot of manual work, we took another approach.

We decided that anyone who brought in a Paper Punch card would keep using the Paper Card until it was completed, and that they could combine all of their paper punch cards to make that transition faster. But from that point on, we didn’t give out any new Paper Punch Cards, so anyone who didn’t have a Paper card with them, we would offer to have them start to use the Square Loyalty Program.

This approach really worked well in a couple of ways. First, it eliminated the manual work of transferring points over, which would have taken a lot of time and would surely lead to a lot of mistakes. We don’t give our employees access to our Customer Directory, because we want things to be as simple for our staff as possible. Because the whole point of adopting this automated Square Loyalty system is to simplify and reduce the manual work that our employees have to do, we didn’t want to add in the complications of training our employees how to adjust points manually again.

Second, it acted as a sort of staggered approach, where we started out with only a small number of customers using the new system. This gave us an opportunity to fully test out the program with much lower stakes. Instead of having all of our 10,000+ customers immediately trying to use the new system, it started out with only a few each day. It was a nice smooth transition, with all of us learning as we went, and getting more comfortable with the new program.

Third, even though we told customers that we were still accepting the old paper punch cards, our customers became really excited about the new Digital Loyalty program. In fact, many of them decided to not even bother using their paper punch cards anymore, and just jumped onto the new digital program.

Key Points & Summary

We started using Paper Punch Cards from our first day open, and while it worked well for many years, there were definite downsides. They were a pain to keep track of, didn’t work with our online orders, expensive to reorder, didn’t give us any data, customers kept losing them, and even worse they were getting disenchanted with our program and didn’t want to use it anymore. We started transitioning over to Square Loyalty, and have only had great experiences with it so far.

Overall, we absolutely love the experience of using Square Loyalty. It’s such a smooth and simple way to run a Rewards and Loyalty Program while using Square Point of Sale, and at this point it’s hard to even consider using anything else. Read my next article to do a deep dive into all of the benefits and downsides of each of the features of Square Loyalty.

Customer Loyalty, Part 1: Why Rewards Programs are Important for your Business

Article originally written for and featured in Square’s Seller Community:

New customers are expensive.

Think of all of the time, effort, money, and aggravation, you spend on marketing in order to try and get new people to come in through the door or make a purchase. Customer Acquisition Cost is the amount of money a business spends to attract new customers, and it ends up being a huge amount.

While continually gaining new customers is a key part of growing your business, keeping your current customers happy and coming is even more important. This is integral not only for building a solid customer base, but also for your profit margin. The cost of keeping your existing customers coming back, is luckily much lower than getting new customers through the door. As a result, these customers are incredibly valuable to the success of your business.

Customer Retention

Customer Retention is essential to running a successful business. But how do you actually manage to retain them and get them to come back?

Once a customer walks through the door, then it’s up to you, your products & services, customer service, and atmosphere to make a great impression and win them over. But even if all of these are perfect, and your customers love what you have to offer, they still might not always come back.

Several studies show that getting customers in through your door the first time is the hardest, and that there’s around a 5-20% chance that new customers will make a purchase. Then if they come in once, there’s a 60-70% chance that they would come back and make another purchase. And if they come back a third time, there’s an even higher probability that they will keep coming back and become a customer for a long time.

Once you have recurring customers, they’re incredibly valuable. If they start coming back then they’re going to keep coming back, and they don’t cost you as much to get them back through the door each time.

So how do you get your customers to come back that second, third, fourth, fifth, and infinity times?
A very effective way to keep your customers happy and coming back regularly is through some great customer Loyalty & Rewards Programs.

Why Do Loyalty Programs Work?

So you know that getting people coming back is important, but why should you consider using a loyalty program to do so?

The simplest answer is that loyalty programs work.

Loyalty Programs turn your products and your business into an adventure and a game. Gamification is a proven psychological phenomenon that absolutely works and appeals to humans at a base level. By creating a goal that they want to reach, or a game that they want to beat, Rewards Programs work really well to draw people in and to keep coming back to complete it. Instead of just buying ice cream, or burgers, or wine, or clothing, your customers are also buying a mission and trying to complete a quest, and if they buy into that then they instinctively want to finish it.

Dangling a carrot for your customers to continue reaching towards will absolutely keep them coming back. Even if that reward is not something huge but rather a little token of appreciation, as long as it’s somewhat compelling, it will be a reward that people will have an innate desire to get. Think about the tickets and prizes at a place like Chuck E. Cheese or Dave & Busters. The prizes are never anything too incredible, but you absolutely still want to get as many tickets as you can, even if you don’t even redeem them for prizes. The worthless tickets themselves are just fun to earn.

And then once they’ve hit that reward, the cycle continues for the next reward, and they can do it all over again. The game and the quest continues.

Types of Loyalty Programs

There are a bunch of different kinds of Loyalty and Rewards programs that you can incorporate into your business.

One way is to create a series of recurring Sales & Coupons that you send out and incorporate into a schedule every year. I would recommend being conservative with how often you send out coupons and hold sales. Constantly having sales on a weekly or monthly basis might unintentionally encourage customers to only come during these sales, making you lose out on a lot of profit. Depending on your product and the average time between visits of your customers can determine how often is best for you to discount your products and services. Holding it off to once or twice a year is a great way to balance loyalty and encouraging people to come in, and not having them rely on only coming during a sale.

Another great way to help encourage your customers to come back at least once per year is through Birthday Rewards. Setting up a system like Square Marketing that can automatically collect customer’s date of birth & send out a coupon to redeem for their birthday is a great way to entice customers. It can get them to come in at least once a year, which will hopefully then help the habit stick and keep them coming back throughout the year.

But the main focus of this series will be the classic Purchase Based Loyalty & Rewards Programs. The most classic example is Punch Cards, but there are a lot of different ways to structure your program depending on the nature of your business.

Key Points & Summary

Because it’s so hard to get people in the door the first time, but easier every time after, returning customers are absolutely vital to running a sustainable growing business. Implementing Loyalty and Rewards programs is proven to be an effective way to keep your customers engaged and coming back. Whether it’s simple paper punch cards, a referral system, birthday rewards, or something else that fits your business, doing something to keep folks coming back regularly is key.

Follow along to the next parts of this series to learn how I put my Loyalty Program together, the pro’s and con’s of Square Loyalty, and tips and suggestions of how to put your own Loyalty & Rewards program together.

Digital Menu Boards: How and Why to Modernize Your Shop’s Displays

Article originally written for and featured in Square’s Seller Community:

Things change with your business. Expenses go up and then your prices go up too. You come up with a new idea and your product line changes. With a standard Menu Board, it takes time, money, and effort to change your menu. You might have a chalk board that can get messy, or a magnetic or vinyl board with new pieces that need to be made, or even a printed board that needs to be completely replaced.

Because of the added effort and cost, you might even hold off on making any changes to your menu or pricing that it takes. While you never know when this might happen, it’s a lot easier to make these changes with a Digital Menu Board.

We took the jump and set up TV Menu boards in our store, and have seen so many benefits as a result.

My Shop’s Menu Board Journey

I own and run Pesso’s Ices & Ice Cream, a small ice cream shop in suburban Queens, New York. We make every flavor ourselves right in the back, so we constantly change up our flavor line up, with brand new creations replacing older and less popular flavors that are due to retire. We’ve had anywhere from 60 to 130 flavors at any point in time, so it was next to impossible to keep our menu accurate.

When we started, the shop came with a Glossy Paint Marker style menu board already installed, which was pretty difficult to update, and got very messy very quickly. We then upgraded to a printed foam core menu board that we couldn’t add to, so it would be up for anywhere from 1 to 4 years. Our interim solution was to add a White board underneath it with New Flavors, but it wouldn’t solve the problem of having old flavors up on the menu that we couldn’t remove.

We piloted the idea of switching to Digital Menu Boards by replacing that dry erase board with two TVs, as a test run to see how it would look and work. The test worked well enough, so the next year we went on to upgrade our entire menu board to digital, with a total of 9 TVs. We have now been using our digital only menu board for over 4 years, and we absolutely love it, and so do our customers.

Our menu and flavor list is always up to date, so we never have customers asking for flavors that are on the board but we don’t have anymore. This saves time and aggravation for both our customers and our employees, since what they see is what we have. We can change our prices or flavor names at the drop of a hat if needed, without needing to invest money or wait to do so. I also worked in a couple of slideshows to showcase featured flavors, products that may not be at the top of mind, and just add an extra visual appeal with irresistible mouthwatering photos and videos.

Setting it Up

We needed a system that was easy for me to set up, and even easier for my employees to keep updated and reset if anything went wrong.

When I first started searching for options, there didn’t seem to be any popular easy & cheap system of setting this up. Every system I saw had expensive hardware plus additional expensive monthly subscription fees. So instead, I came up with my own. It took just the right combination of hardware and software to make it happen, and I’ll walk you through what I did.

This is by no means the definitive way to set up a digital menu board for your business, it is simply just what I did for my shop.


First came the idea of using Google Slides as the main system. This works both for static Menu Boards that just display a single page of set flavors or Menu Items, as well as Slideshows that automatically flip through a multiple pages or images. The only thing that it wouldn’t work for is videos, which wasn’t really a deal breaker for us, but I did find a work around of converting short videos to GIFs that do work with Slides. The best way to display the Google Slides would probably be on a Web browser, so I started the rest of this process with the end goal of a Web Browser, specifically Chrome, in mind.

I set up a separate Google Account to log into whichever device I would use to display these screens and slides, so nothing else would accidentally be displayed. I created my slides in my main Google Account, and then shared them with this secondary account. I then went into Google Slides, and clicked on Publish to the Web so I could get a standard Web Address that I could open on a Web Browser. I then logged into Chrome with this secondary account, and set up my Bookmark Bar with the links to these slides.

I also installed and activated this chrome extension called Keep Awake ( so that the slides would keep playing and it wouldn’t time out and turn off the TVs.

It took some creative problem solving to get some flavor lists to extend across two monitors, but lining up the graphics and extending borders through slides made it work really well.


With the software side ready and figured out, I had to figure out what the best hardware would be. Smart TV’s might not be able to have Google Slides or a Web Browser, and neither would an Apple TV or a standard Chromecast, without having an additional device streaming or casting over to it.

In my search, I found these Google Chromebits ( which are little sticks that plug right into an HDMI port, but are actually essentially full-stand alone chrome-based computers. This isn’t a perfect solution because they need a keyboard and mouse each, so I found these multi-device bluetooth Keyboard ( and Mouse (, that each work with 3 devices. So we set up 9 TVs, so we bought 9 Chromebits, 3 Keyboards, and 3 Mice. In the end, we didn’t really need the keyboards because we only use them to type in the password once in a blue moon if it gets reset, and we can use the on-screen keyboard with the mouse instead of having three physical ones.

We wall mounted the TV’s and when we angled them down, there was enough space to mount Surge Protectors behind them, with enough outlets to plug in the TV’s and the Chromebits.

Things I Would Change

After living with this setup for 4 years, we’re really happy that we made the switch. It’s so easy to always have an always updated menu, without having to do any manual work of printing things out, or holding off on a change until we have the time or money.

One thing that is less fun, is that there are a lot of moving parts and things that can fail. Lately we’ve had a few of our Chromebits and TVs just fail and need to be replaced, connection issues with the keyboard and mouse, and a few other issues. Most of these are to be expected, with them being always on 24 hours a day, every day of the year.

The biggest downside is that with COVID, we’re doing all of our sales from our Walk Up Window. Because of the way it’s positioned, the only real way we can set things up is with a printed menu. There isn’t enough support to set up TV’s by the window, so while customers can see the TV’s from our other window from outside, when they order they’re stuck looking at our printed menu. So we’ve had to continue to update that one in the meantime while we figure out a better solution. But hopefully soon we’ll go back to having customers in our store and taking full advantage of our beautiful Digital Displays.

Key Points & Summary

Overall, despite it not being perfect, we absolutely love having our digital menu boards. It’s been a huge upgrade to your business operations, and has made things smoother, easier, and faster for our customers and our staff. Making the switch has definitely been worth it, and I can’t imagine running my business without our new menu displays.

How and Why to Support Your Community with Donations from Your Business

Article originally written for and featured in Square’s Seller Community:

My dad and I opened up our small neighborhood ice cream shop in 2004, and we’ve made it a point to donate to local groups and run fundraisers for our community every year since the beginning.

Using your business to support local organizations in your community through fundraisers and donations is a great way to solidify your presence as a contributing member of your neighborhood, and to help those in need. 

Donations to local organizations can really help your community and neighborhood grow and prosper. Fundraisers also end up spreading the word about your business, act as great word of mouth advertising, and have the wonderful side effect of helping your business too. 

Fundraiser events are a complete win-win in providing much needed funds to local schools and groups in your area, and helping you gain new customers along the way. New and existing customers will come because of the fundraiser, and if all goes well, they’ll keep coming back after.

But where do you start? How do you hold a fundraiser with your business? What’s the best way to donate products to local community organizations?

There are so many great ways that you can help your community, each one of them with different levels of contribution, cost, and potential growth to your business and neighborhood.

Even with the pandemic, it’s still absolutely possible, and potentially even more important to hold COVID-safe fundraisers and help your community and your business prosper.

Product Donations

Depending on your business, the best way you might be able to help your community is by donating your product. This was especially shown during the pandemic, but it’s a great thing to do every year no matter what. Restaurants can donate food to those in need, barbers and beauty salons can give free haircuts, and businesses of all kinds can set up drives in their shops where customers can buy their products and immediately donate them.

Whether it’s local shelters, food banks, or first responders, showing your appreciation and care for your neighborhood by donating your products and services directly to people who need it the most is a wonderful thing to do.

Donating your product is a great choice because it doesn’t directly cost you that much to do something great for your area. You’ll only have to front the product cost, and maybe some labor, but overall, it’s a wonderful way to give back without putting too much out from your business.

Sports Team Sponsorship

Another great way to get started is by sponsoring some local sports teams for kids or adults. Depending on what your business offers and who your target audience and market is, finding a little league team or adult recreation league could be a great fit.

There are a few ways to sponsor a local team. Usually they all involve an initial yearly donation of some amount of money, and then depending on the amount and the team, the perks you get may vary. Some will put your logo and information on a banner that they put up at games, others might give you a shout out and put your logo in their newsletters and website, and others might even put your logo on their uniforms.

My favorite benefit of building a relationship with local teams is that they often establish a routine of coming to your shop after every game. Some of our best times were when the little league team would come by to our ice cream shop after their games.

Gift Card Donation

Another great simple way to contribute to local groups is by donating Gift Cards. You can donate them to specific groups in need, or as raffle prizes for local organizations’ fundraisers. These might be at physical events, virtual events, or ongoing efforts held over longer periods of time.

Having your Gift Cards as a potential prize does double duty for your business. Not only will the person winning the prize come to your business to redeem the credit, everyone else who hears about the raffle or event will see your business name as being part of it, which serves as a wonderful extra advertising and promotion opportunity. 

Donating a Gift Card is a great way to go because it doesn’t immediately cost you any money. You would just have the product cost eventually if the winner ends up coming in and using it, which they may not even end up doing. 

If you pick the right Dollar Amount for the gift card, the winner might even end up spending extra money to redeem it. You can calculate and find out your average transaction cost using Data from your Square account and donate a card value that is a little bit less, a little bit more, or a multiple of one of those, in order to increase the chances of them spending more money. For example, If your average transaction cost is $15, either donate a $10, or $20, or $25 Gift Card.

To set up gift cards for donation, you can create a 100% Off Discount called “Gift Card Donation,” and then just load up the Gift Card as usual and apply this discount to the transaction.

In-store Fundraising Events

Holding an in-store fundraising event is the peak of traditional community fundraisers. A lot of organizations would love to have a fundraiser at your shop, and tying a donation to a percentage of sales is a great way to drive traffic to your business. Typical percentages I’ve seen range from anywhere from 10% to 25%, but you can use your best judgement according to your business and the organizations you’re teaming up with.

It’s very important to figure out what policies you want in place and write them all down into a document that you would send out to any organization that has interest in holding a fundraiser with your business. 

Here are some different ways you can run your fundraiser, and different options of policies you can adopt for your business:

Day of the Week

The first step of figuring out the process of how to hold a fundraiser in your store is to pick only one day of the week to hold them. This makes it easy to set a schedule and keep track of your fundraisers. A great way to do this is to use your Square Data to find out what your slowest days of the week are. Using that information, and your knowledge of your business, you can pick a day of the week and set all fundraisers for that day. 

Using one of your slowest days helps boost the sales for that day of the week, and makes it easier to handle a hopefully higher influx. You don’t necessarily need to bring in extra employees to work that shift, depending on how big the organization is and how large the turnout is. Especially if it’s on your slowest day of the week, you may be fine with your standard number of employees, so it doesn’t end up costing you extra to run the event.

We found that Thursdays are best for our business since it’s close enough to the weekend that more people are more likely to come out, and it helps boost sales into the weekend. Because of this, every fundraiser we have is set for a Thursday.

Donation Option 1: Percentage Of All Sales

The easiest way to run, and calculate the donation amount for, your in-store fundraiser event is by donating a flat percentage of all sales for a certain period of time. Whether it’s a full day, week, or just a couple of hours, donating a straight percentage of all sales is a quick and easy calculation. You can use your Square Reports to filter your sales for any period of time, and then just calculate the percentage you chose to get your donation amount. 

While the benefits of this system is that it’s super easy to calculate and run the event, there are some definite downsides. The main one being that it’s easy to be taken advantage of, and your business can end up donating a lot of money. With this method, there is no real way to tell how many customers were sent by the organization you’re helping to raise money for, and how many customers would have come either way. If you end up having more regular customers than fundraiser customers, the organization may end up getting more money than they earned. 

As a result, some groups might catch on and may not necessarily work as hard to bring in people, if they know that they’ll be getting a good amount of money either way. Or even if they do work hard and promote it, if they still don’t end up bringing in that many people, they may get more than they’re due, and cut into your profits too much.

While contributing to your community is a good thing, you are still running a business, and do need to think about your profits, especially if you’re holding a lot of fundraisers pretty frequently. 

So what if this ends up being too much and there’s too much risk? That’s where our next method comes in:

Donation Option 2: Percentage of Participating Sales with Flyer

A safer way to run things is by donating a percentage of only participating sales. The main way to do this is to have customers show a flyer, either paper or digital, when they make their purchase, and to only count those sales towards the total. This is the method that we use at my shop.

This is much more fair, both for you and for the group you’re donating to. The amount that they get relies completely on how many people they bring that show up, and how much money they spend. The better they promote the event, and the more they support your business, the more money gets donated to the organization. 

There are of course a few downsides of this. First, groups may end up earning less than they might expect if they’ve done fundraisers with other businesses where they have received a flat percentage of all sales. If your business isn’t a good fit with their organization’s members, or if it’s not a good day of the week for them, then the donation you give might be lower than they hoped. Although you do always have the option of adding some money to the donation total if you’d like to contribute more directly from your business.

This method also involves a bit more work. We decided to take the extra step of creating the Flyers for each group, so it’s all uniform and is easier for our employees to recognize and verify. I just made a simple template, then I change the name and date on the flyer, and then I email the organizer a PDF file for them to distribute. 

There’s also a few extra steps of calculating the donation amount, but it’s not too difficult, especially with the amazing tools that Square provides for free. We created an item called Fundraiser and priced it at $0, and each time a customer shows a flyer, our cashier adds that item to the order to mark the transaction. For Online Store sales, I also made a $0 Coupon Code and put that on the flyer as well. When the event is over, we open the Transactions tab on the Square Web Dashboard, search for the item called Fundraiser which ends up only showing transactions that have that item, and then filter by the hours of the event. Repeat that process for the Coupon Code. After this is done, this page shows you the Total Number of Transactions and the Total Dollar Amount Collected, which you can then use along with your set donation percentage to calculate how much money the organization will get.

Again, while this does take a couple of extra steps, we’ve found that it’s incredibly worth it to make sure that we’re being fair to all of the groups and to our business. It’s a great thing to donate, but being consistent and making sure your business survives is important too.

Key Points & Summary

If you’re a local neighborhood small business, then your livelihood really depends on the support of your community. So it’s a really great thing to develop a full relationship with community members and organization, and give back to them whenever you can. With in-store fundraising events and donating money, gift cards or products to local organizations, you can show your appreciation to your neighborhood, while also advancing your business along the way. Get creative and find new groups in your area that need support, and be an amazing giving resource to your community.

Good luck, and let me know how it goes!

How I Grew my Seasonal Business to be Open All Year – Seasonal Part 1

Article originally written for and featured in Square’s Seller Community:

My father and I opened up Pesso’s Ices & Ice Cream, our small neighborhood Ice Cream shop in November of 2004. It’s very much a weather-affected business, with the busiest part of our year definitely being the summer. Throughout the years we’ve tried both sides of being seasonal, with years where we were open all year, and years where we were closed during the winter.

Before we owned it, our location was already Italian Ice shop run by our friends for a couple of years years, and we had the opportunity to take over and make it ours. Because the main product was Italian Ices, and we are in the super residential town of Bayside, New York, they started out as Seasonal.

The shop was open from March through November, and closed for the 3 Winter months. So after only 1 month of owning our shop, we closed down for the winter. Luckily, we saw this as a huge benefit because we were able to reflect on what we learned in our first month of the business, and take a few months to clean up, organize, make a plan, and get ready for the future of our shop.

From Seasonal to Open All Year

From the beginning, our goal was to build up our customer base so that we did not have to be seasonal and closed in the winter. We figured that since we’re paying rent and utilities anyway, being open all year would only increase our income and our profit. It took a couple of years for us to feel comfortable doing it, so we started small. We started small, staying open an extra month the first year, and then 2 months the second year, and then finally in third year we able to just stay open.

Changing our Hours

As a little compromise, and as a way to save some money and run our business as efficiently as possible, we set up different Store hours for each of the seasons. In the summer we open the store the earliest and stay open the latest, and in the colder months, we open later and close earlier. In the first few years we made these decisions using a lot of guess work, but since we switched to Square in 2012, we were able to use Sales Data through Square to figure out our optimal opening and closing times, which was incredibly valuable.

Expanding our Offerings

We made a plan to try to expand our offerings to help draw in more customers during the traditional non-ice-cream-weather. We tried Coffee and Espresso, Pretzels and Hot Dogs, Candies, Fruit Smoothies, Soups, Hot Chocolate, and more. While this strategy and these offerings can definitely work for a lot of businesses, because we were already established and were known as a seasonal Ice Cream shop none of these really stuck or resonated with our customers. Once we realized that, we decided to hunker down and focus on our primary offerings because that’s what we were experts at.

Shifting our Focus

Raise your hand if you’ve ever excitedly proclaimed “Let’s go out for Italian Ices!” on a beautiful sunny day.

Yea. I didn’t think so.

While Italian Ices are fairly popular in New York City, their demand pales in comparison to the global appeal of Ice Cream. So we channeled that universality and made a plan to become a destination for Ice Cream. Even though we made Ice Cream and Gelato ever since we opened, we sold much less of them because people knew us primarily for our Ices. So we started by improving our Ice Cream and Gelato recipes, adding more unique flavors, and we made it a point to offer more customers tastes of our growing Ice Cream line.

Next, we rebranded and changed our name from Pesso’s Italian Ices to Pesso’s Ices & Ice Cream. We updated our website, our in-store signage, our online listings like Yelp and Google, and of course our social media accounts. A huge benefit of changing your name on Facebook is that it automatically sends out a notification to all of our followers, which is a great easy way to bring your brand front of mind to your fans. And with all of that our SEO, or Search Engine Optimization, improved dramatically. Because we had ‘Ice Cream’ in our name, we showed up higher on the search results when people searched for that category on Google and Yelp.

Educating our Customers

Since we were busy enough in the warmer months, we figured the best solution would be to encourage our existing customers to come in the Winter months. The big Italian Ice chains in New York are all seasonal, and even though we are a small family business, the majority of our customers naturally thought that we were closed in the winter. So the biggest step of convincing our existing customers to come more in the off-season was to first educate them that we were still open when it’s cold out.

We tried a lot of strategies to make sure our customers would know that we were Open All Year. We attached a banner to our awning, put signs on our walls in our store, edited it onto our photos, a headline on our website, put it on our business cards, the labels on our Pints, signs on our Napkin Dispensers, and more. We also used the amazing Square Marketing tools to send out Email campaigns to reach customers outside of our store.

One of our most effective marketing and education tools is what we call Bag Tags. We print out little slips of paper to advertise any specials, new flavors, or anything else that we’d like to promote, that we put into every bag when customers take items to go. Towards the end of our season in late July and August, we made some Bag Tags that simply said “Pesso’s is Open All Year,” which definitely helped get the word out to a huge chunk of our customers.

Expanding our Reach

Our next big move was to improve our marketing to reach more new customers. We switched our focus from posting in local newspapers and giving out coupons, to higher yield and further reach mediums. We started by revamping our Social Media Strategy. Instead of randomly taking photos and posting them as we felt like it, we built out a schedule on a spreadsheet to keep our posts varied and engaging. We started out posting every other day, and more recently we’ve started to post everyday. We set up our Instagram posts to automatically post Twitter too, to have a wider reach and impact with no extra work.

Tough Decisions – Going Back to Seasonal

All of this work definitely paid off to a certain extent, and our sales in the off-season months consistently grew year after year. However, it wasn’t enough for us to cover all of our expenses, and didn’t end up working for us, and it may not work for you. So after 10 Years of trying to make Open All Year work, we decided to shift back to being a Seasonal business.

Stay tuned for my next post to read about why decided to go back, how we did it, and what we learned along the way.

How to Make Square Data Work for You

Article originally written for and featured in Square’s Seller Community:

The data that Square gathers and creates for you is so extremely valuable to keep a pulse on your business, as long as you know where to look. To see just how valuable, check out my other post all about How I Revamped My Business Thanks to Square Data. But that’s how I did it, let’s talk about how you can do it too.

How to Do it Yourself

So what steps do you take to you reap the benefits of Square Data yourself? Here are some simple ways to start:

1. Assess Your Item Library

Take a good hard look at your in-store menu and the items you sell. Think about how they are naturally organized and how that would translate to organizing them them on Square using Categories, Items, Variants, and Modifiers.

Categories would be things like Entrees, Appetizers, Desserts, or Shirts, Pants, Socks. Items would be individual pieces of merchandise like Steak or Men’s Socks. Variations are different versions of one Item, like 8 oz and 12 oz versions of the item Steak, and Red and Blue Men’s Socks. They can be easily tracked to different SKUs, and can be set up to be the same or different Prices. Modifiers are great for add-ons or changes to an item, and can be an added cost, or no charge. They’re great for changes like adding extra onions, or if a customer ordered a chicken or steak taco.

There are millions of ways to set up your Item Library, with a lot of different factors to consider. It all depends on your store set up, and your goals. Striking the balance between data and efficiency is incredibly important. A lot of data is valuable, but if you have a long lines and need fast transaction times, the time it takes to enter in too much data can slow down your service.

2. Organize Your Data

Once you’ve started to make sales with your new Item Library, it’s time to organize that data. Think about your goals and business needs, and build our your spreadsheets accordingly.

What trends do you want to track? What is important for you to find out? Do you want to track how your business is doing year after year? Do you want to see what items or categories sell better in the winter months than in the summer months? Do you want to know which items or categories have been increasing year over year, and which ones have been decreasing?

Some great trends to track are Sales of All Category, Specific Item Sales Comparisons, Discounts, Sales vs. Labor, Hourly Sales, and more! The beautiful thing is that you can create your own spreadsheets for each and every trend you want to follow, with whichever metrics and variables work best for you.

On your Square Dashboard, you can run Standard Reports or create Custom Reports, and either export the data, or type the data into your new spreadsheets manually – whichever works best for you!

3. Analyze the Trends

Look over all of your amazing new spreadsheets and try to find some useful trends and patterns. The patterns may be comparisons between items or categories, the same item or category over time, or hour by hour sales. Go back to your goals and trends you were interested in, and see what your sales data tells you.

4. Improve your Business

As the brave and wise G.I. Joe once said, “Knowing is half the battle!”

Now that you know a little bit more about what’s going on in your business, you can make changes to improve things! Use your newfound knowledge to make changes that will cut costs and increase sales. Whether it’s getting rid of high cost & low sales items, ordering supplies in larger discounted quantities to match historical sales, changing your hours based on sales, or increasing marketing or changing positioning on your menu to promote and sell more of certain items. Implementing improvements based on data is one the best ways to keep your business growing and thriving!

5. Keep the Data Flowing

Don’t forget to keep updating your spreadsheets every month. This way you can continue to spot and track trends, and keep making changes so your business keeps growing!

I hope this has helped gives you some ideas for ways to make your data work for you, and help your business grow as much as it’s helped mine.

Now, I’d love to hear from you:

How has seeing your data helped your business?

What business decisions have you made based on data?

Do you have any Questions?

Comment below and keep the data and the conversation flowing!