# Matthew Caiola

> Matthew Caiola is the New York-based chief executive of 5WPR. An Iona graduate who joined the agency in 2009 and became co-CEO in February 2022, he has led corporate, technology and digital practices and The HOW Agency. His recent writing and research examine how AI-generated answers change brand discovery.

- **Role:** Chief Executive Officer at 5WPR
- **Organizations:** 5WPR, The HOW Agency, Iona University (alumnus), Aerotek (former employer), Avalanche Strategic Communications (former employer), Public Relations Society of America, Little Baby Face Foundation (board member)
- **Education:** Bachelor’s degree in Mass Communication, concentration in Public Relations, minor in Political Science, Iona College (now Iona University)
- **Known for:** Led an emerging technology practice that recorded more than 50% annual growth for three years, as documented in awards coverage., Expanded that department to more than 120 employees and over 100 clients at the time of its awards profile., Silver Stevie, Communications, Investor Relations, or PR Executive of the Year, 2023 American Business Awards.

## Career timeline

- **2005** — Graduated from Iona College; early career included Aerotek and subsequently Avalanche Strategic Communications.
- **2009** — Joined 5WPR.
- **2020** — Listed as president of 5WPR’s Corporate & Technology Practice in O’Dwyer’s directory.
- **2022-02** — Promoted to co-CEO of 5WPR alongside Dara Busch.
- **2023** — Oversaw corporate and technology practices and The HOW Agency; received a Silver Stevie and a Ragan/PR Daily Agency Leader of the Year honor.
- **2025-04** — Returned to Iona as Scholars Day keynote speaker.
- **2026-04** — Co-authored The GEO Reckoning with the 5W research team as CEO.

## Achievements

- Led an emerging technology practice that recorded more than 50% annual growth for three years, as documented in awards coverage.
- Expanded that department to more than 120 employees and over 100 clients at the time of its awards profile.
- Silver Stevie, Communications, Investor Relations, or PR Executive of the Year, 2023 American Business Awards.
- Agency Leader of the Year honoree, announced May 2023, Ragan and PR Daily Communicators of the Year Awards (2022 program).
- Jointly listed with Dara Busch for European CEO’s 2023 CEO of the Year in the Public Relations Industry award.
- 2025 Iona Scholars Day keynote speaker.

## Latest updates

- **2026-06** — Published MediaPost commentary on how AI systems assemble answers and what that means for communications strategy.
- **2026-05** — Co-authored 5W’s banking AI visibility index with Ronn Torossian; the report states a dataset of 31,500 prompts.
- **2026-05** — Published TechIntelPro commentary on structured data and B2B brands’ visibility in AI answers.
- **2026-04** — Co-authored The GEO Reckoning, published April 27, with the 5W research team.
- **2025-04** — Delivered the Iona Scholars Day keynote on April 15.

## Links

- Website: https://www.5wpr.com/about5wpr/management/matthew-caiola.cfm
- LinkedIn: https://www.linkedin.com/in/matthew-caiola

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Profile page: https://yespress.io/matthew-caiola
Published by YesPress — https://yespress.io
Last updated: 2026-10-06