Penta Names Jim O'Leary as CEO to Scale Leading Modern Corporate Advisory Firm

Former Weber Shandwick CEO, Edelman COO and Global Corporate Affairs Practice Chair joins to drive Penta’s continued growth following investment from Shamrock Capital

With Shamrock’s investment, the firm is building a new model for modern risk and reputation advisory: Premium expertise backed by best-in-class AI, technology, data and analytics 

WASHINGTON, D.C. — MAY 14, 2026 — Penta today named Jim O'Leary as Chief Executive Officer, bringing one of the communications industry's most established global leaders to lead the firm through its next phase of transformative growth.

O'Leary joins from Weber Shandwick, where he served as CEO, North America and Global President. Prior, he served as Global Corporate Affairs Practice Chair and U.S. COO at Edelman. Over two decades, he has advised global C-suites through high-stakes challenges at the intersection of politics, finance, culture and technology.

O'Leary is widely recognized as a transformative leader, having scaled Edelman's Corporate Affairs and Advisory Services practice into one of the largest in the industry. He also oversaw the day-to-day operations of Edelman's U.S. business during a period of record revenue growth. After Edelman, he joined Weber Shandwick, where he drove significant transformation including launching Weber Advisory, its high-growth corporate affairs unit, as well as leading on AI transformation.

His appointment follows Shamrock Capital’s investment in Penta in August 2025 to accelerate the firm’s growth across its modern corporate advisory model, underpinned by best-in-class data, technology and its proprietary AI platform. As CEO, O’Leary will continue to expand capabilities and capitalize on opportunities emerging across today’s rapidly evolving communications landscape.

"Today's executives need to be continuously attuned to the web of stakeholders who shape their reputational, regulatory, and commercial outcomes. They need more signal, more precision, and faster action than yesterday's advisory model can deliver," said Laura Held, Partner and member of the Executive Committee of Shamrock Capital. "Legacy agencies built on geographic breadth and traditional marketing services models are giving way to something different: expertise-driven, technology-native advisory firms built to move at real-time speed. That's the model we're betting on at Penta, and Jim is the right person to take it to the next level."

Penta’s senior counselors bring decades of experience in public affairs, financial communications, corporate affairs, brand strategy and crisis communications. The firm’s proprietary artificial intelligence platform processes more than 25 million daily signals across 100-plus languages, surfaces direct insight from thousands of policymakers worldwide to model anticipated policymaker behaviors, and delivers real-time analysis of how narratives form and travel across stakeholders.

The result is an advisory model powered by real-time insights and predictive analytics that helps business leaders anticipate risks and get ahead of emerging stakeholder tensions in a reputation and risk environment where political, cultural, financial, and technological threats compound.

“I've been really impressed by the depth and expertise of Penta's team, and the industry-leading AI, technology and data underpinning the firm's client work," said O'Leary. "The Penta platform gives leaders a level of foresight and precision that just wasn't possible 12 months ago — and roughly 25% of Fortune 100 companies are already relying on it.”

Under O'Leary's leadership, Penta will continue to expand its agentic AI and predictive analytics that power the day-to-day advisory work and will sustain its rapid growth trajectory through both organic and inorganic expansion globally.

Prior Penta CEO Matt McDonald will be moving up to the Penta board and working closely with O’Leary as he steps into the CEO role.

“Penta has been disrupting communications with an integrated approach to data, AI, and advisory work, and Jim has been pushing this innovation as a leader in the industry. This is the perfect match, and I could not be more excited to have Jim lead Penta for the next stage of growth,” said McDonald.

O'Leary was recognized by PRWeek earlier this year as Agency Professional of the Year and was the driving force behind Weber Shandwick's first-ever win for Outstanding Corporate Agency. A recognized leader in AI in communications, his authority on artificial intelligence has been profiled in Semafor and Fast Company. He has been recognized by PRWeek’s 40-under-40 and Dashboard 25 as one of the most innovative professionals in the industry.

A longtime advocate and fundraiser for rare disease research, O’Leary serves on the board of Lurie Children's Hospital in Chicago.

About Penta Group

Penta is a modern corporate advisory firm helping global organizations navigate the intersection of political, reputational, financial, and technological risk. The firm combines senior advisory expertise with a proprietary intelligence platform to help clients understand and act on the stakeholder ecosystems that shape their business outcomes.

Penta is headquartered in Washington D.C., with offices in London, New York, Brussels, Dublin, Singapore, San Francisco, and Hong Kong. The firm is backed by Shamrock Capital. For more information, visit www.pentagroup.com.