Career Summary

Director of PMO Operations | IT Professional Services Executive | Sales & Marketing Executive| Management Consulting Lead | Professional Services Consultant | Program & Project Manager

C. Gary Rupp brings more than 25 years of executive-level experience in information technology (IT), spanning consulting, marketing, professional services, program and project management, and sales. Mr. Rupp has directly managed more than 30 enterprise-class IT programs and projects, with the last nine years focused almost exclusively on managing large enterprise Health IT Programs at the US. Department of Veterans Affairs (VA), CORAM Specialty Infusion Services, and Kaiser Permanente.


Reads Gary’s latest book, Scaling Scrum Across Modern Enterprises. Implement Scrum and Lean-Agile techniques across complex products, portfolios, and programs in large organizations. Now available from PACKT Publishing and

Gary is also writing and publishing a series of books titled Building Our Digital World, on software and systems development practices. Available on, the BODW series of books are written for both novice and expert practitioners in IT, and includes the following books:

  • SDLC Foundations– An introductory and historical guide to software and systems development.
  • Tools and Templates– Improving the quality and consistency of outcomes in software development and agile processes.

Career Highlights

  • Managed a series of projects within a high-tech company over three years with a total budget of $52 million.
  • Most client and contractor staff managed in a single project/ program is ~115; while simultaneously planning forty-one software development, testing and deployment increments and managing twenty-five “Active State” Development & Testing Increments
  • As Director of a business consulting services development group, led a team of software and content developers responsible for creating and deploying reusable professional service offerings, methods, and tools in support of 4000 business and IT consultants who were operating across the world.
  • Product and Program Manager within an international IT firm, responsible for the development, sales, and P&L of a suite of computer-aided systems engineering (CASE) suite of tools for functional, data, information, process, simulation, and object-oriented analysis/design modeling.
  • In Capture/ Business Development Manager roles, have successfully bid and won numerous IT Professional Service Contracts, ranging in value up to $50 Million.
  • Sales VP for a Silicon Valley Startup Business Intelligence Portal company from its second round of funding through its successful IPO, hiring and managing 45 direct sales professionals and 13 indirect sales representatives.
  • Area VP of Worldwide Sales and Marketing within the eBusiness Division of a $900 million software firm, responsible for direct and indirect sales of middleware, database, and software development tools.
  • As an IT Professional Services Director and Practice Manager, over three years, profitably grew the organization from a startup, and successfully bid and won a multi-award federal contract that placed IT 100 professional service consultants.

Professional Certifications

  • Certified SAFe 5 Program Consultant ID No. 24488227-0897
  • PMI certified Project Management Professional (PMP) – PMP Number: 243644.
  • Scrum Alliance Certified Scrum Master (CSM) – ID No. 650996.
  • Scrum Alliance Certified Scrum Product Owner (CSPO) ID No. 650996.
  • Certified Large-Scale Scrum (LeSS) Practitioner.