Executive Summary
Carolyn Pleiss currently serves as Senior Vice President and Chief Information Officer (CIO) at Cox Enterprises, a position she has held since October 2, 2022. Based in Atlanta, Georgia, she is responsible for leading enterprise-wide technology strategy, delivery, architecture, security, compliance, and application development across the organization. Carolyn plays a critical role in defining IT capabilities that support the company’s broad business objectives.
Professional Experience and Career Progression
Carolyn Pleiss has been with Cox Enterprises since 2007, initially joining Cox AutoTrader Publishing before transitioning to Autotrader.com. Her tenure there is marked by her leadership in the company’s agile transformation, successfully overseeing the adoption of agile methodologies to improve operational efficiencies and delivery processes. Prior to her CIO role, she served as Vice President of Strategy and Value Realization within Cox Enterprises, emphasizing her strategic approach to bridging technology and business outcomes.
Earlier in her career, Carolyn held senior technology roles including Senior Director of Information Technology at Autotrader and roles at Harris Connect and Publishing Concepts, demonstrating a consistent track record in technology leadership within the publishing and automotive domains.
Core Competencies and Strategic Focus
- IT Strategy & Enterprise Architecture: Directs the formulation and execution of IT strategies that span Cox’s diversified business units.
- Security & Compliance: Oversees cybersecurity initiatives and compliance programs critical in protecting the company’s data and maintaining regulatory adherence.
- Application Development & Agile Methodologies: Led the agile transformation at Autotrader.com, showcasing expertise in driving iterative development cycles and cross-functional collaboration. She holds an Agile Certified Professional (ACP) certification.
- Portfolio & Project Management: Has experience leading project management offices and elevating project management standards aligned with business goals.
Recognition and Industry Standing
Carolyn has been acknowledged as one of the "100 Women Worth Watching" by Diversity Journal and a “Woman of the Year” honoree, illustrating her influence and leadership in technology and diversity advocacy. She is recognized for her commitment not only to operational excellence but also to mentoring and developing talent within the technology community.
Educational Background
Carolyn holds a Bachelor’s degree in English from Creighton University and possesses a certificate in project management from the Project Management Institute, contributing to her holistic understanding of technology management and leadership.
Organizational Impact and Leadership Style
As CIO, Carolyn is a key member of Cox Enterprises’ corporate leadership team, delivering IT capabilities applicable enterprise-wide, which include optimizing architecture, enhancing security posture, and accelerating application lifecycle development. Her previous roles show a strong ability to align technology solutions with strategic business value realization, suggesting a leadership style that emphasizes measurable outcomes and continuous improvement.
Relevant Industry Activities
- Participates actively in leadership forums such as C-level technology leadership summits.
- Advocates Agile practices and strategic planning frameworks within Cox, positioning technology as a driver of innovation.
- Engages in mentoring and career development initiatives focused on diversity and inclusion in technology.
This detailed profile of Carolyn Pleiss highlights her strategic IT leadership at Cox Enterprises, her proven ability to drive agile transformation and enterprise-wide IT initiatives, as well as her role as a recognized industry leader fostering technology innovation aligned with business growth objectives.
