25,000+ Customers Nationally
289+ million transactions annually
#1 Customer Rated iPad POS
ShopKeep puts your cash register on an iPad. It’s intuitive and easy to use. We were founded by a merchant, so we know simple, powerful solutions beat complicated bells and whistles every time. With ShopKeep, you can accept any form of payment and you get essential features like automatic inventory tracking, employee management and real time sales reporting anytime, anyplace.
Our mission is simple:
Empower independent business owners to dream big and fight smart.
The Sheep Shoppe
A cozy, colorful yarn shop
The Juice Box
A hip, laid-back juice bar
A warm, charming restaurant and catering company
The Stand Branford
A hybrid farmer's market, food truck, restaurant, and bar
The ShopKeep Story
ShopKeep was born in NY
Apple launched the iPad and we moved our software from desktop to tablet
ShopKeep reached 100 employees
We opened new offices in Belfast, Northern Ireland and Portland, OR
Acquired Payment Revolution and launched integrated payment processing
ShopKeep was ranked #116 on the Deloitte Fast 500 Fastest Growing Tech Companies in North America
ShopKeep partners with JUUL to reduce youth access to vapor products
President and CEO
Michael DeSimonePresident and CEO
Michael is a global chief executive, with more than 25 years of experience working within the financial services and technology industry. As President and CEO at ShopKeep, Michael leads strategy to sustainably grow and scale the business, which processes more than $8.5 billion in transactions annually. Prior to joining ShopKeep, Michael was President and CEO of Borderfree, where he was responsible for the overall strategic direction including the company's transformation from an online currency conversion service to a provider of global ecommerce solutions. He led the company through their successful IPO in 2014 and its sale to Pitney Bowes in 2015. Michael has also earned recognition on the Smart CEO's Future 50 list in 2015 and was named an Ernst & Young Entrepreneur of the Year.
Chief Financial Officer
Ed NeumannChief Financial Officer
At ShopKeep, Ed oversees the company's finance, legal, facilities and human resource functions. Ed has more than twenty-eight years of financial and operations experience. He was previously the Chief Financial Officer of PeopleDoc, a cloud-based SaaS company offering HR Service Delivery platform solutions. Prior to that he was the Chief Financial Officer at Borderfree, an international ecommerce technology and services company, overseeing the growth and expansion of the business through its initial public offering and subsequent acquisition by Pitney Bowes in 2015. He also spent nearly a decade at Charming Shoppes, Inc., a women’s multi-channel apparel retailer, and held several key executive roles, including Senior Vice President and Chief Operating Officer at Charming Direct, the company’s ecommerce division. Ed holds a B.S. in Accounting from West Chester University in Pennsylvania.
Chief Marketing Officer
Andrew GorrinChief Marketing Officer
At ShopKeep, Andrew leads all go-to-market strategies and initiatives for the sales and marketing departments. With over 15 years of experience advocating for small business, Andrew brings a focused passion to the small business industry. Andrew started his career with Brodeur Worldwide, and spent five years with American Express in senior positions focused on customer engagement and acquisition for its small business division, OPEN. He was also a Senior Manager at Dove Consulting, where he led client engagements focused on the retail financial service sector. Prior to joining ShopKeep, Andrew served as the Senior Vice President for Marketing at Web.com, leading the company's customer acquisition strategy, its cross-sell and upsell programs, its inside sales team and managing the product portfolio for its custom website and social media product lines. Andrew holds an MBA from Georgetown University and a B.A. from the University of Rochester.
Chief Technology Officer
Daniel RolnickChief Technology Officer
At ShopKeep, Daniel leads the company's strategy across key technology initiatives, aligning technology-related decisions with the company's strategic vision. Prior to joining ShopKeep, Daniel served as Chief Technology Officer for Yodle, an online marketing service that helps local businesses build a strong online presence. Daniel spent the eight years prior at Barclays Capital working on POINT, a SaaS platform for 200 of the largest global investment portfolio managers, where he held the position of Head of POINT Application. Daniel received his Bachelor of Science in Computer Science with honors from the Georgia Institute of Technology.
Executive Vice President
Crystal CaligiuriExecutive Vice President
At Shopkeep, Crystal leads Customer Success and is charged with leading our award winning merchant onboarding and Customer Care teams, as well as growing the Shopkeep Capital business. Crystal leads teams across all four Shopkeep offices: New York, Belfast, Portland and Chicago. Crystal brings with her over 20 years of experience, focused in operations, customer success, and technology. Prior to Shopkeep, Crystal held many high profile roles at Gilt Groupe, focused on growth, including customer experience, supply chain, real estate, strategy and planning, project management, purchasing and merchandising operations. She also launched Gilt's international business in 2011. Crystal has an MBA from Columbia Business School and an B.S. in Economics from the University of Pennsylvania.
SVP of Product Management
Mike SommersSVP of Product Management
At ShopKeep, Mike leads the expansion of the features and capabilities of ShopKeep's point-of-sale system. Mike has more than 21 years of experience working within the online software space. He started his career with Blue Marble ACG, then spent seven years at AOL as Vice President of Product Development. Mike also led the development of online solutions for small business while as Chief Product Officer at WeWork and as Senior Vice President of Product at Booker. Most recently, Mike served as Senior Vice President of Product at Beatport, the leading online distributor of electronic music, where he led the company's transition to a consumer-facing platform following its acquisition by SFX Entertainment.
SVP of Partnership Development
Nicole MaioSVP of Partnership Development
At ShopKeep, Nicole leads Partnership Development and growth of ShopKeep’s referral, wholesale, and product integration channels. Nicole brings with her over twenty years of experience, fifteen of which she has spent spearheading Strategic Business Development and Revenue Growth in fintech companies. Prior to ShopKeep, Nicole spent eleven years at cross-border payments provider Payoneer, in critical Enterprise Sales and Global Business Development roles. Most recently, Nicole held the position of Vice President, Business Development, where she led revenue growth with ecommerce platform partners around the world. Prior to Payoneer, Nicole held positions with TSYS Prepaid and Prepaid Media. Nicole holds a B.A. from Wesleyan University.
SVP of People
Kelly LeydenSVP of People
At ShopKeep, Kelly leads all People strategies and initiatives including talent acquisition, organization development, employee experience and internal communications. With over 19 years of experience in large, small and mission driven businesses, Kelly brings a focused passion for aligning the consumer and employee experience. Kelly started her career with Ingersoll Rand, where she realized the huge impact that people have on business. She spent time at Iron Mountain and at eBay in senior positions leading global reorganization and building new business. Kelly then became the Head of People for Learnvest, where she worked through its’ sale to Northwestern Mutual, helped to lead the digital transition and finally the integration of the two companies. Prior to joining ShopKeep, Kelly served as the Head of People for S’well, leading the company’s People strategy.