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Debra Keeling-Christmas

WIBN Mentor
Photo of Debra Keeling-Christmas

Biographical Info

Debra Christmas is a seasoned leader in the high tech field with over 35 years of experience managing all aspects of information technology.    Prior to joining Gartner Canada, Debra was Vice President of Hewlett-Packard Software Technical Sales leading a team of over 300 technical software sales professionals across North and South America, contributing to $500M in sales for HP Software.  She has led IT organizations in both the public and private sectors driving change and transformation through engaged, diverse and high performance teams around the world. Her previous roles include Vice President for Strategic Services and Global Accounts, Chief of Staff, and Director of Strategy and Operations for Presales for the IT Management Software Business Unit across Canada, the United States and Latin America and National Manager for Channels, Alliances and Partners in Canada.  Her team of enterprise software consultants and solution architects covered the entire portfolio (applications, security, operations, big data and information management) in companies like Disney, Walmart, Verizon, Bank of America, JPMC, and State Farm.  Between her two tours of duty for Hewlett-Packard she was Chief Information Officer of the City of Kingston and Kanata where she lead major technology and business transformations to optimize costs and deliver progressive and innovative constituent services. Her role as an Executive Partner provides her the honour and privilege of working with senior leaders – both technology and business focused – on their strategy, execution of their initiatives, organizational challenges and their own professional development. She is a sounding board and a conduit to the Gartner organization to help them drive results and achieve the targeted business outcomes.


She has championed diversity and women in IT issues throughout her career sitting on Diversity and Inclusion committees within HP and was executive sponsor of the first ever Black Employee Network for HP Canada. She was one of five employees around the globe profiled in HP Software for their career journey and contributions.  She has contributed to her profession through years of service to the Canadian Information Processing Society chairing local chapters in Kingston and Ottawa and was Vice President of the Municipal Information Systems Association during her tenure in the public sector.  She was nominated as one of Canada’s Most Powerful Women in the Scotia Bank Corporate Award category. She speaks regularly at industry events and conferences on leadership and transformation in IT including International Women’s Day in Canada and abroad.  She has travelled the world as a facilitator for Manager Milestones, an innovative leadership development program for HP and recipient of the Brandon Hall Gold Excellence Award for Learning in 2012. She has engaged with hundreds of leaders across continents and cultures to help them develop leadership skills to drive business results and enhance employee engagement.  She is the Founder and Co-Creator of PACE (Pathway to Communication Excellence), a Brandon Hall Gold Excellence Award winner for Best in Competencies and Skill Development in 2014. She is founder of Stiletto Gladiators, a not for profit organization delivering mentorship services, leadership assessment, development and diversity coaching. She is a member of the Women in Business Network, WxN, and Women of Influence. She is a motivating and inspirational leader and is particularly passionate about the development of women in IT. She is certified in Tilt365 and Leadership Circle, a comprehensive leadership assessment framework based on “Mastering Leadership”.

Categories: WIBN Mentor / Champion