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Ashley Dittmar-Galassi has a varied work experience beginning in 2006. Ashley started as a Student Coordinator at DePaul, where they compiled a bi-monthly newsletter and facilitated and planned meetings and events for the Office of Academic Enhancement. In 2007, they worked as a Marketing & Creative Media Intern at The Legal Balance Inc. The following year, they were a Medical Market Research at Medquery, and a Marketing Intern at Kaplan. From 2009 to 2015, Ashley worked at Michael Quinlan, Inc. as a Crucial Conversations Master Trainer, Senior Facilitator, and Director of Operations, where they facilitated Crucial Conversations courses and provided coaching, mediation, conflict resolution, and cultural change resources to a variety of Fortune 500 companies. Since 2015, Ashley has been a Sr. Manager of Faculty & Master Trainer, and a Manager of Client Success, Master Trainer & Client Coach at Crucial Learning (formerly VitalSmarts).

Ashley Dittmar-Galassi completed their Bachelor of Science (B.S.) in Marketing, Communication from DePaul University in 2009. Ashley also obtained a Bachelor of Science (BS) in Marketing and Communication from DePaul University in 2009. Prior to this, they attended Elkhorn High School. Additionally, Ashley has obtained several certifications, including a Certificate of Completion in The 7 Habits of Highly Effective People from the American Management Association in 2014, an Influencer Master Trainer from VitalSmarts in 2013, a Crucial Conversations Master Trainer from VitalSmarts in 2009, a Change Anything Certified Trainer, Corporate Athlete Training, Getting Things Done Master Trainer, and Master Trainer Crucial Accountability.