About Us

Our Story
Stingray Investigations & Consulting is a home-based consulting and investigation LLC that specializes in educational human resources systems, investigative services, job descriptions, strategic planning, training, and temporary administrative support. With over 20 years of experience in educational leadership and more than three decades in a variety of K-12 settings, we are ideally situated to provide customized solutions addressing the needs of any size institution.
Our unique ability to design personalized solutions ensures compliance with necessary regulations, policies, or specific requirements. We understand that each community has individual needs, environments, priorities, and points of pride. Therefore, we don’t believe in a one-size-fits-all solution. Instead, we focus on creating strategies that are tailored to meet the unique needs of your situation.
What Sets Us Apart
What truly sets Stingray Investigations & Consulting apart is our unique ability to design solutions that are personalized to meet the unique needs of each situation, while ensuring that the solution is compliant with any necessary regulations, policies, or specific requirements. We understand that each community has individual needs, environments, priorities, and points of pride. Therefore, we don’t believe in a one-size-fits-all solution. Instead, we focus on creating strategies that are tailored to meet the unique needs of your situation.
Moreover, our extensive experience in the field, coupled with our deep understanding of the educational sector, allows us to provide insights and solutions that are both practical and effective. We are not just consultants; we are partners who are committed to helping our clients achieve their goals and enhance their HR practices. Our commitment to personalized service, combined with our expertise and passion for education, makes us a trusted partner for educational institutions seeking to optimize their HR processes and improve outcomes.
Stingray Investigations & Consulting: Your Partner in Educational Success
Background in Industry
Stingray Investigations & Consulting was born out of a recognition of the increasing complexities and demands in the educational sector, particularly in the realm of human resources. The founders, Charles and Debbie, bring a combined experience of over 60 years in education, management, human resources, operations, and leadership. Their extensive experience spans a variety of K-12 settings, including elementary, middle, and alternative schools, small districts, large districts, and educational service districts.
The education sector is increasingly focused on optimizing human resource processes to meet regulatory requirements and enhance staff performance in order to affect student academic outcomes. With growing compliance demands and a heightened focus on staff development, there is a need for specialized consulting services that can assist educational institutions in navigating these complexities, while at the same time building and maintaining positive relationships.
Stingray Investigations & Consulting was started to provide a resource to fill the knowledge and training gap; as well as create customized solutions that support student academic success, so that leaders can focus on ensuring that students have the highest quality teaching and learning environment possible.
About Charles
Charles is a seasoned Chief Operations Officer and Co-Founder with over 35 years of comprehensive management experience across diverse industries. Charles began working with others as a mentor and coach at the Boys & Girls Clubs of America, which is where he developed his love of helping others. He worked in health care while he was going to college for nursing, which built a deep foundation and understanding of the importance of compassion and service excellence.
Along the way, Charles became interested in medical technology and transitioned into the technology sector. He has since excelled in training and staff development, equipping clients and end users with the skills and knowledge necessary to leverage innovative solutions effectively. As Director of Project Management, his expertise in meeting deadlines while complying with multiple federal and state regulations, enabled Charles to design projects with smooth transitions focused on the client’s needs.

In an effort to help a friend whose husband had just passed away; Charles began legal service of papers. As with everything he does, what was supposed to be a temporary arrangement turned into several years of experience investigating fraudulent reports, tracking individuals, documenting circumstances both in writing and through photography, and testifying in court on behalf of clients. This experience taught Charles how to remain calm regardless of circumstances; and to focus on factual information. Charles Simons, PI-ID: 126317, is also a licensed private investigator.
As a dedicated family man, Charles is married with five children and takes pride in being a grandfather to 11 grandchildren. This commitment to family reflects his values of teamwork, support, and nurturing relationships, which he brings into his professional endeavors. With a rich blend of experience in operations, technology, and legal services, Charles offers clients a strong commitment to customer service and excellence, regardless of the need. His unique skill set and unwavering dedication to service make him a valuable partner for any organization.

About Debbie
Debbie Simons has served in leadership roles in Human Resources for over 20 years in a variety of settings include medium and large districts and ESDs. She has extensive experience as an educator and human resources professional, and includes time as an elementary school principal, middle school principal, director of human resources in middle and large school systems, and assistant superintendent of teaching and learning. She also is a consultant, helping districts with various projects.
Debbie served on the Oregon School Personnel Association (OSPA) board for eight years, including as president, and she has taught classes for new human resources professionals. She returned to the OSPA board in 2023 for another term; and is currently serving as the Interim Executive Director of OSPA. In addition to human resources, the portfolio of programs she has overseen includes technology, food services, athletics, special education and student learning. Debbie was named Oregon’s HR Director of the Year in 2024 and currently serves as the Region 1 Representative for AASPA, the American Association of School Personnel Administrators.
Debbie began her educational career during her senior year of high school when she worked halftime in Mrs. Peacore’s second grade classroom. In addition to leadership positions, she has also worked as a substitute teacher, middle school teacher, teacher in an alternative program, volleyball and basketball coach, Title One Coordinator, and leadership and honor society adviser. She received her undergraduate degree from Western Oregon State College, now Western Oregon University. She earned her master’s degree in Curriculum and Instruction from Southern Oregon University and administrative license through Portland State University. She enjoys spending time with her husband, five children, 11 grandchildren and 4 great-grandchildren, along with cooking, gardening and traveling.
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