Former Gilt Groupe and Shoptiques executive will focus on operations and lead customer support for Company’s clientele

ShopKeep, the cloud-based technology solution that transforms an iPad into a connected cash register that is used by more than 23,000 businesses, today announced the appointment of Crystal Caligiuri as the Company’s new Senior Vice President of Operations and Customer Care. Caligiuri, who will report to CEO Michael DeSimone, will lead both operations and ShopKeep’s Customer Care functions, ensuring the Company’s small business clientele are provided with the high-quality support necessary to their success.

Caligiuri’s appointment is representative of the Company’s dedicated efforts to being an end-to-end solutions provider for its customers – one that best understands their needs and how to support them. In her role, Caligiuri will continue to strengthen and build on ShopKeep’s customer care efforts, helping maintain and enhance its client support services for an expanding customer base. Additionally, her depth of experience working with leading-edge ecommerce and retail businesses will strengthen ShopKeep’s versatility in serving clients not only as they navigate current challenges, but also as they anticipate and evolve for the challenges of tomorrow.

“Ensuring that each interaction between ShopKeep and our customers is seamless, timely and trouble-free is key both to their success and our own.  Building on such mutual success is foundational to ShopKeep’s mission to serve as a true ally to small business,” said ShopKeep CEO and President, Michael DeSimone. “Crystal’s years of experience leading customer-centric functions will continue to strengthen our commitment to helping independent merchants manage smarter businesses on the ShopKeep platform. We look forward to the talent and leadership she will add to our team.”

Caligiuri brings more than ten years of experience in operations and customer support leadership across the technology, ecommerce and retail industries. She most recently served as executive vice president at Shoptiques, an online marketplace for global boutiques. Prior to that, she held a series of leadership roles at Gilt Groupe, a leading flash-sale and ecommerce platform, most recently occupying the role of vice president of business operations and customer support. Previously, Caligiuri served as a consultant at a self-run consulting firm, Caligiuri Business and Operations Consulting, and at New York Consulting Partners before that.

“The convergence of tech innovation, ecommerce growth and evolving consumer preference is quickly reshaping the small business landscape, both physically and digitally. I’m thrilled to join ShopKeep and work with a team at the intersection of new, emerging POS technology and the age-old needs of everyday merchants,” said Caligiuri. “For independent storefronts, ensuring that business is continuing as usual is critical. At ShopKeep, we are steadfast in delivering a solution that makes ‘business as usual’ better, smarter and easier – all while providing the comfort of timely, high-quality customer care at a moment’s notice for clients in need.”

Caligiuri received her Bachelor of Science in Economics from the Wharton School at University of Pennsylvania and received her MBA from Columbia Business School.


About ShopKeep

Everything ShopKeep does supports growing and independent businesses. Built by and for small business owners, ShopKeep provides an intuitive, secure, iPad point-of-sale system with POS software that empowers merchants to run smarter businesses by optimizing staffing, regulating inventory and accessing sales reports and customer information on one seamless, cloud-based platform. With more than 23,000 customers, ShopKeep’s award-winning customer care team is available to help 24/7 and provide a robust support network for growing business owners. Ranked one of the fastest growing North American tech companies by Deloitte and a member of Apple’s Mobile Partnership Program, ShopKeep is headquartered in New York, with offices in Portland, Chicago, and Belfast. Follow @ShopKeep on Twitter, join the discussion on the ShopKeep blog or visit to learn more about ShopKeep’s POS system.

Press Contact:

ICR for ShopKeep
Laura Anderson

Yamarie Grullon

Yamarie Grullon has years of experience creating helpful & engaging content for small business owners. As Director of Content Strategy at ShopKeep, a leading iPad Point of Sale System, Yamarie provides merchants with practical advice on all things related to business or point of sale.