How Leveraging Online Ordering and POS Can Eliminate Restaurant Chaos

Key Takeaways

• Transitioning to digital means paying attention to your menu and training staff to make sure everything runs smoothly on the new systems.
• Having your own website and ordering system is a game-changer, especially if you want to keep more of your sales instead of giving a cut to third-party platforms.
• Setting up a loyalty program and syncing it with your POS system helps track customer retention and can boost sales through smart features like cross-sells.

The restaurant world has changed quite a bit with the introduction of new tech like ordering platforms and points-of-sale (POS).

Switching to these tools can represent a great opportunity for growth, but it can also be overwhelming at first.

Jordan Silverstein, the Executive Vice President at YourMenu, has experience helping restaurants navigate this shift, and I reached out to him to get his input.

In this interview, Jordan told DesignRush some of the biggest challenges restaurants face when transitioning, while sharing practical advice on how to make it smoother.

Who is Jordan Silverstein?

Jordan Silverstein joined YourMenu in 2022 as its Executive Vice President, bringing over a decade of experience in POS systems, payment processing, and online ordering for SMBs. For the past three years , Jordan has guided YourMenu’s go-to-market strategy while shaping sales and operational frameworks that support rapid growth.

If you’ve seen Hulu’s The Bear, you might have a pretty good idea of how chaotic running a restaurant kitchen can be.

There’s a specific episode, Review, where the show’s restaurant struggles when adopting an online ordering system, resulting in a massive number of orders in just a few minutes.

While The Bear is an over-the-top show, it did motivate us to ask Jordan about the real challenges restaurants face when transitioning to the digital world.

He points out menu engineering and staff training as the most significant hurdles:

“Since not all POS and online ordering platforms work the same way, some parts of the menu can be lost in translation such as modifiers,” Jordan says.

“Additionally, staff members typically need retraining to understand how to perform the same functions they’re used to on the system.”

To navigate these challenges, Jordan mentions that restaurants should pay close attention to their menus and go through the new system thoroughly.

“That’s the only way to ensure the menu matches their standard,” Jordan says.

Jordan also suggests training staff members from the top down, so that senior employees can provide quick assistance to newer team members.

Another recommendation is to build a proper website for the restaurant as soon as possible, as that can impact sales revenue by as much as 30%.

Meanwhile, Caleb Bradley, CEO and founder of Bighorn Web Solutions, emphasizes how critical it is for restaurants to rethink their digital presence with a more strategic, user-focused approach.

"Many restaurants underestimate the importance of delivering an app-like experience on their websites that is fast, easy to navigate, and optimized for mobile users. Menus should be treated as conversion tools, not static lists, with clear images and structured layouts that guide decisions.

A simplified checkout flow and well-placed upsell prompts can make a measurable impact on order value and overall conversion rates." Bradley adds.

“If you have no way for customers to order online from your restaurant, you’re missing out on tons of sales.

If you are only listed on 3rd party delivery platforms, but do not have your own 1st party ordering page, you’re going to be losing about 30% for each sale to 3rd party companies,” Jordan explains.

For restaurants that simply cannot have a website up and running, YourMenu offers a “website package” option.

“We provide restaurants with an SEO-friendly 5-page marketing website, designed to help them rank organically for valuable keywords that relate to their restaurant in their locality.

The site can be edited by the restaurant directly in the YourMenu back office with no web development knowledge needed.”

Spicing Up Menus and Training

Along with a website and POS options, Jordan also believes restaurants should have a customer loyalty program to effectively measure customer retention.

“From the loyalty system, restaurants can track how many new sign-ups they're getting and how many points customers are earning, in order to measure customer retention.”

Jordan mentions that YourMenu has a partnership with LoyalZoo to address that need, providing a seamless in-store and online loyalty program.

“When a customer orders from a restaurant on YourMenu, or visits that restaurant in-person, they accumulate points.

Those points can be redeemed in-store and online for rewards. Restaurants can customize the program to decide how many points someone gets per dollars spent.”

Along with these solutions, Jordan highlights the introduction of “a ton of features” since its launch in 2023.

“We’ve integrated with two of the largest POS providers for restaurants in the U.S., Clover POS and Square POS Integration.

By integrating with these POS systems, restaurants can quickly sync their existing menu from the POS to their YourMenu online ordering page,” Jordan says.

Other features include SMS marketing, reputation management, and cross-sells, a function that allows restaurants to increase their average order amount.

“For example, if someone adds a burger to their cart, YourMenu will prompt them to see if they might also be interested in a side of fries, or maybe a milkshake.”

Cooking Up a Strong Online Presence

Speaking more specifically about how YourMenu significantly helped a client grow, Jordan highlights their partnership with Heritage India, a local restaurant in D.C.

“To help them generate over 100 new online orders per month, our team helped them get set up with a new POS system directly integrated with our online ordering system.

To drive sales, we helped with printed marketing flyers and SMS campaigns to reach more customers.”

A good digital marketing strategy can truly help drive sales. According to Jordan, that starts with an optimized Google Business profile.

“Customers normally look for restaurants through Google or other popular search engines, so ensuring that your profile on these platforms is accurate and links to your website is critical.”

Jordan also offers a piece of advice regarding the most important criteria to evaluate when choosing an agency to work with: customer support.

“The best system in the world is useless without proper support from their customer service team.

Their team should be knowledgeable and ready to help you with onboarding, technical questions, marketing assistance, and anything else related to online ordering and POS.”

The Key Ingredient for Restaurant Tech’s Future

Online ordering and POS systems are relatively new additions to the restaurant ecosystem, with plenty of potential for future improvements.

Jordan believes that AI will play a major role in how online ordering and POS systems evolve.

“We think customer experience will be elevated with AI and machine learning. We’ll see AI powering more personalized menus, smarter upsells, and predictive ordering, like suggesting new dishes based on past behavior,” Jordan says.

We also expect systems to auto-optimize menu layouts based on what’s selling or what the restaurant wants to sell more of.”

As Jordan’s insights show, transitioning to the digital space can be a great opportunity for restaurants to grow — hopefully, with a little less drama and tension than in The Bear.