Meet & Greet: Jason Richelson of ShopKeep POS, Point of Sale System for Local Small Businesses

Firmology’s SMB Tech Meet & Greet series takes an inside look at the technology available to business owners and entrepreneurs, straight from the founders who built them.

Jason Richelson Headshot (Close-Up)

Name: Jason Richelson
Title: Founder and CEO
Company Name: ShopKeep POS
Company One-Liner: ShopKeep makes cloud-based point of sale software that helps retail shops and restaurants make smarter decisions that grow their business. Founded and designed by a merchant, we understand the challenges retail businesses face every day.
Location: SoHo, New York, NY

Tell us about your background:

A former technology consultant and trader, I opened a specialty food and wine store in 2004, which I grew with my partner to employ more than 70 people in the Brooklyn and lower Manhattan branches.

My experience as a retailer allowed me to understand the challenges of growing a retail business, which is why I created ShopKeep POS in 2008. 

What does your company do and what problems do you solve for small businesses?

shopkeep-pos-logoShopKeep’s mission is to be an advocate for retailers, making it simple for them to start, run, and grow a successful business. We aim to solve several problems for merchants:

  • Cost of entry

A traditional POS system can cost up to $12,000 or more for two registers, licensing fees, Windows server, installation, configuration and staff training. That doesn’t include ongoing maintenance fees or the hourly price tag for help if something goes wrong.

With the cloud and iPads, all that goes away. ShopKeep costs retailers $699 for all hardware essentials when they bring their own iPad, and because everything runs in the cloud, there is no need for maintenance. The subscription is $49 per month including unlimited customer care.

  • Reliability and always-on service

ShopKeep is cloud-based, so there’s no need to worry about servers going down. It also works offline, so retailers can continue to ring up cash sales if the internet goes down.

  • Running your store without being there physically at all hours

The iPad register is synced with the store’s BackOffice, where business analytics, such as sales, inventory, product, and staffing information, are stored. Store owners can access this information from anywhere, including via a dashboard app on their smartphone, so they can monitor sales and staff anytime.

  • Ease of setup and use

Small business owners are not technology experts and typically find point of sale technology complicated and intimidating. Our mission is to make point-of-sale easy, approachable, and friendly.

Retailers typically set up ShopKeep on their own and are up and running in minutes. Most people have used an iPad, so a shop owner’s staff need minimal training. To take a recent example, all payments at the Telluride Film Festival in Colorado this year ran on ShopKeep, iPads, and the cloud. One hundred volunteer cashiers rang up $12,000 sales in four days with only 30 minutes of training.


How did you come up with the idea for your company?

In 2004, my partner and I opened a wine store in Brooklyn, New York. Over the ensuing years, one store grew into three as we added a grocery store and a coffee shop. Keeping track of our sales and inventory became increasingly important and more complicated. We were using a traditional Windows-based point of sale system and regularly experienced a number of technology challenges. But the moment  I knew that I’d had enough was when our servers crashed while I was on vacation in 2008, essentially crippling the business. As soon as I got home, I tried to find a cloud-based alternative, but I couldn’t find anything suitable. ShopKeep POS was born that day.

What makes your company different from competitors?

There are two fundamental ways that ShopKeep differentiates itself from the many POS systems available to shop owners:

First, we are built from the ground-up by a retailer for retailers and small businesses. As a former small business owner myself, I know what retailers go through every day. I understand the challenges of growing a retail business and have built ShopKeep with that in mind every step of the way. ShopKeep is designed to help shop owners and managers make smarter decisions, be more efficient, be more successful, and have a better day.

Second, we have invested heavily in our Customer Care team to provide the best customer service in the business. I’ve stood behind the counter and I understand how important great support is to busy store owners. That’s why we have an award-winning team available to respond to merchant calls, emails, and chats seven days a week.


What are the most important things a small business should consider when choosing technology to help with the business?

When choosing technology, retailers need to be careful not to get locked in to long term contracts and to make sure they have the flexibility to evolve if they need to.

Small business owners need the power to choose what is right for their business. They’re asked to make an incredible number of upfront commitments just to enter the marketplace, and, when they’re starting out, the business could look completely different six months down the line.

It’s important for retailers to have choice and flexibility when setting up and growing their businesses, which is what our platform gives them. They can customize the interface, choose the right credit card processor and package for their business, and choose to go month-to-month with ShopKeep if they like.

What other companies or entrepreneurs within the technology industry do you admire and think other SMBs should know about?

Tony Hsieh and Zappos are a huge inspiration and influence on me due to their dedication to customer service, team culture, and making their customers happy every day. I even sent our director of Customer Care at ShopKeep to spend a week with Zappos to bring those learnings back into our business.

I also admire Salesforce and Marc Benioff for his leadership on SaaS and disrupting the traditional CRM software market. I see us as disrupting the traditional POS market today in a similar way.

Any news, special deals, or events Firmology readers should know about?

As part of our commitment to helping retailers succeed, we recently launched an online resource center for small businesses dedicated to ‘Lean Retailing’. is full of helpful advice from small business experts about starting, running, and growing a brick and mortar retail store or business.

Inspired by the methodologies of the technology startup industry, Lean Retailing is about taking a data-led approach to starting and growing a business and using business analytics to make good decisions. It’s also about how to take advantage of cloud-based technology to run your business more efficiently. Store owners can visit to find out more.

ShopKeep also recently announced a 2014 plan to expand further into bars and restaurants, and retailers can expect several new releases over the coming months.

Lastly, we continue to offer 30-day free trials for retailers who want to sign up and see how ShopKeep POS works for their business. Store owners can visit to find out more.

Firmology Readers: Let’s hear your thoughts!

1) Have a question or comment about ShopKeep POS? Drop Jason a note in the comments below.

2) What do you think of our SMB Tech Meet & Greet series thus far? Are there other questions we should be asking? Are any of the questions above unclear or could be asked in a better way? Let us know in the comments below or email us at

 If you’re the founder of a tech company and would like to be featured on Firmology’s SMB Tech Meet & Greet series, please email us at with the subject line: Meet & Greet Submission.

Want to learn more about other small business tech founders? Check out these past Meet & Greet profiles:

Meet & Greet: David Hassell of 15Five, Employee Engagement and Feedback Reports

Justyn Howard of Sprout Social, Social Media Management & Engagement Platform

Joshua Reeves of ZenPayroll, Modern & Delightful Payroll for Small Businesses

Amit Kumar of Lexity, Ecommerce and Marketing Apps to Help Online Businesses Grow

More SMB Tech Meet & Greet series guests

About The Author

Jason Richelson is the CEO and Founder of ShopKeep POS, a provider of cloud based point-of-sale software for managing retail shops and restaurants.  A former technology consultant and trader, Jason opened a specialty food and wine store in New York in 2004, which he grew to employ more than 70 people in the Brooklyn and lower Manhattan branches. Jason’s experience as a retailer inspired him to create ShopKeep POS.