Jim O'Leary

Jim O’Leary advises leading executives as they navigate complex challenges at the intersections of business, society, culture and policy. As Penta’s CEO, he is relying on decades of expertise leading strategy and execution to build a modern corporate advisory — where senior counselors help leading organizations navigate high-stakes challenges proactively and with precision, backed by best-in-class data and intelligence.

Prior to joining Penta Group as CEO, O'Leary served as CEO of The Weber Shandwick Collective, North America and Global President, with oversight of all major global markets including EMEA, APAC and LATAM.

During his tenure at Weber Shandwick, O’Leary reshaped the firm's capabilities, building Weber Advisory, a high-growth corporate affairs unit, and establishing the firm as a leader on AI-enabled advisory with the launch of Weber I/O — the firm’s agentic artificial intelligence capability. His leadership brought Weber Shandwick its first-ever Outstanding Corporate Agency recognition from PRWeek, and in 2026, he was named PRWeek's Agency Professional of the Year.

Prior to joining Weber Shandwick in 2023, O'Leary spent 15 years at Edelman, where he served in a number of U.S. and global leadership roles with escalating responsibility, including U.S. Chief Operating Officer, Global Chair of Impact & ESG, and Corporate Affairs Practice Chair.

O'Leary is a longtime counselor to CEOs and their boards in business-critical situations. His clients have included Walgreens, McDonald's, McKinsey & Company, PayPal, Mitsubishi Heavy Industries, General Electric, Hewlett-Packard, Bombardier, and Raytheon.

While at Edelman, O'Leary transformed Edelman’s global corporate affairs and advisory services practice through a focus on client-centricity and innovation. His contributions included Edelman’s first-in-the-industry capability in CommsTech, the development and launch of Edelman’s Business Transformation and Business Marketing units, the establishment of a new global practice focused on social impact, and the conception and authorship of flagship IP, "The Future of Corporate Communications".

Prior to joining Edelman, Jim served as a communications leader and on-the-record spokesperson for Honeywell. He has been recognized in PRWeek's Dashboard 25 as one of the industry's most innovative professionals and was previously named to PRWeek's "40 Under 40". A prolific fundraiser and advocate for rare disease research, he sits on the Foundation Board at Lurie Children's Hospital and on the Chicago Planning Council's Board of Governors.