Jason O’Brien

Jason O'Brien

Professional Experience

As newly appointed chief information officer, Jason O’Brien is an executive leader who builds agile teams to solve hard problems. He brings more than 16 years of information technology experience providing services in both large and small organizations. His expertise lies not only in the technical arena but also in business strategy, IT policy/management, and team leadership.

Most recently, he served as the vice president of CaaS Services and Worldwide Operations for Interactive Intelligence with responsibility for 16 datacenters worldwide hosting over 70,000 call center agents in a 24/7/365 environment. In his role, he conducted iterative competitive analysis strategy to ensure the company offered superior products to customers, and he increased margin from -11% to 70% in two years while maintaining 150% year over year growth.

In addition to his Interactive Intelligence experiences, Jason has worked in a variety of entrepreneurial environments serving as the chief technology officer for Courseload, where he won the 2011 Indiana Innovation Award. He also served as the director of managed hosting at ANGEL Learning (acquired by Blackboard) and, prior to that, Bank One Chicago where he was vice president of Shared Application Services/IT Architect Consulting.

Jason is a graduate of Indiana State University, and he has taught at WestWood College. He thrives in a fast-paced environment and is excited to have joined the VMS team.

Areas of Expertise

  • Information Technology
  • Infrastructure/Architecture
  • Product Strategy
  • Problem Solving
  • Leadership

Professional and civic organizations

  • Honors and Certifications
  • Microsoft Certified Solutions Expert

Professional and Civic Organizations

  • Brownsburg Masonic Lodge
  • VisionTech Angels
  • SmartFile Board Member


  • Indiana State University, BS