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Richard Wollenberger has extensive work experience in the field of information technology. Richard began their career at Forsythe Computers in 1989, working as a Salesline Consultant before transitioning to the role of System Engineer. In 1993, they joined WF Corroon as a Network Systems Manager, where they managed staff and technology during a transition from Mac to Novell servers. Richard then moved to Buck Consultants in 1996, working as a Client Services Manager in Purchasing.

In 1998, Wollenberger joined Osborn & Barr Communications as the IT & Facilities Manager, where they oversaw all IT and facilities needs for the organization. Richard was responsible for managing the technology, staffing, and budget, as well as overseeing office moves and openings of remote offices.

In 2003, Wollenberger became a self-employed contractor, providing consultation services to various companies in St. Louis, including Smurfit-Stone, Monsanto, and Anheuser-Busch. During this time, they worked as the Owner & Consultant at First Call Technology Solutions.

In 2006, Wollenberger joined Parents as Teachers National Center as the Director of Information Technology and HIPAA Compliance and Security Officer. In this role, they led and managed cost-effective technology solutions aligned with the nonprofit's objectives. Richard oversaw IT strategy, applications, infrastructure, IT operations, and the service desk. Parents as Teachers National Center provides home visiting services for families with children from prenatal through kindergarten age. Wollenberger continues to serve in this role.

Richard Wollenberger attended Bradley University from 1980 to 1984, where they obtained a Bachelor of Science degree in Theater Arts Production with a minor in PR and Graphic Design. In 2006, they received the ITBMC (IT Business Manager Certification) from Belmont University in Nashville, TN. In 2015, they earned the Certified HIPAA Professional and Certified Security Compliance Specialist certifications from ecfirst. Most recently, in 2020, they obtained the Certified Cyber Security Architectâ„¢ (CCSAâ„¢) certification also from ecfirst.