Crystal Caligiuri



Please enter your comment!


Crystal joined ShopKeep in 2016 as Chief Customer Officer. Born out of frustration with the traditional cash register business, ShopKeep's iPad-based point of sale system was designed by a retailer with a noble aim.

Previously, she was a Member Of The Board Of Advisors at PennPAC and before that a VP, Operations, Customer Care and International at Earlier in her career she worked with as a VP, Operations, Customer Care and International.

She graduated from Columbia Business School with MBA and in The Wharton School with an undergraduate degree in Economics.



  1. I had been with the company for several years prior to Crystal’s arrival, under the Department that she now leads. She came in and immediately went to work drastically improving every facet of the department, from implementing new support channels to aiding in the founding of new sub-departments. Crystal has the perfect of balance of business awareness and people awareness. By that I mean that she understands that sometimes you need to make changes that people may not like or agree with for the betterment of the business but she knows how to implement those changes in a way that builds trust with her employees. That trust becomes even stronger as time goes on and you understand the astounding impact her contributions and tough changes made. She is a champion of women in the tech industry. She works tirelessly mentoring other women inside and outside of the company to reach their full potential. She is always learning and growing and tells her story about her arrival in tech in such a personable way that you learn to stop doubting yourself as a women in a male dominated field. She has contributed endlessly to Women in Tech and continues to do so. The key strength that Crystal has is her ability to build trust. Trust is crucial when leading a team, and Crystal seamlessly leads several teams and thus, several sub teams within the organization and I would be hard pressed to find a single employee that does not have trust in Crystal’s vision and leadership.

    Staff, submitted on

  2. Crystal promotes a positive work culture that brings people together. She was integral in helping to lead ShopKeep’s Women in Tech event last year, from the overall purpose and flow of the event, all the way to sourcing from her network of incredible women in leadership roles at other companies to fill out the speaker panel. She has a deep commitment to strengthening her direct team, as well as contributing to the betterment of our organization and industry cross-departmentally. I feel as though she cares about my career development, even though I am not on her team. She reaches out to me to check-in on things and to ensure I am flourishing in my role. Amongst her direct contributions to the organization, a key achievement came with her leadership for the launch of ShopKeep’s chat option as a new customer communication channel. The launch of this channel significantly improved the number of small business owners that our customer care team was able to help. Additionally, since Crystal has joined ShopKeep, she has contributed towards the company’s scale and rapid growth and serves ShopKeep small business customers with the highest standard of care and support.

    Mid-level professional, submitted on

  3. Crystal stands above most executives I have had the opportunity to work with. Every day is seen as new from every aspect, so we can drive towards a goal, but pivor as needed to balance the company and the customer.The immense humility Crystal shows gives way to collaborative environments where everyone grows together. Crystal challenges norms and really brings a team up to speed to think nothing is impossible and productive is better than perfect. These strengths have brought our company and employees into the best days our teams have had.

    Senior-level professional, submitted on

  4. People leadership and development, leveraging data and analytics to make smart business decisions, always open to a new challenge, very high professional and emotional maturity

    Senior-level professional, submitted on

  5. NA

    NA, submitted on

  6. NA

    NA, submitted on

See All Reviews >