# Robert (Robbie) O’Brien

> Robert (Robbie) O’Brien is an Irish technology founder from Derry, the founder and former CEO of MetaCompliance, and co-founder and chairman of Safe Harbour Security. His work centres on employee security awareness, practical cybersecurity for smaller organisations, and leadership accountability. He also hosts The Cybersecurity CEO Podcast and writes a Substack for business leaders.

- **Role:** Co-Founder and Chairman at Safe Harbour Security
- **Organizations:** Safe Harbour Security, MetaCompliance, Capita, Intergraph Corporation
- **From:** Derry, United Kingdom
- **Nationality:** Irish
- **Education:** Queen’s University Belfast
- **Known for:** Founded MetaCompliance in 2005 and led it until the 2023 CEO handover., Ernst & Young Entrepreneur of the Year finalist., Received a 2019 CV Corporate Excellence Award in the IT CEO category.

## Career timeline

- **Early career** — Worked for Capita and Intergraph Corporation.
- **2001** — An earlier technology business failed in the dotcom crash, an experience he later discussed in his writing.
- **2005** — Founded MetaCompliance.
- **2019** — Received the IT category’s Most Influential CEO of the Year award at the CV Corporate Excellence Awards.
- **2020** — Credited author of Cyber Security Awareness For Dummies, MetaCompliance Special Edition, with Geraldine Strawbridge.
- **2021** — Partnered with Tenzing to support MetaCompliance growth; the business had 110 employees and over 900 customer organisations.
- **2022** — MetaCompliance acquired Copenhagen-based MOCH, its first acquisition.
- **2023** — James Mackay became CEO on 3 October; O’Brien moved to Chief Evangelist and initially remained a board member.
- **2025** — Announced his full departure from MetaCompliance in March; received a North West Regional College honorary award for contribution to the economy in October.
- **2026** — Co-founder and chairman of Safe Harbour Security; publishes The Cybersecurity CEO Substack and hosts The Cybersecurity CEO Podcast.

## Achievements

- Founded MetaCompliance in 2005 and led it until the 2023 CEO handover.
- Ernst & Young Entrepreneur of the Year finalist.
- Received a 2019 CV Corporate Excellence Award in the IT CEO category.
- Co-authored the 2020 MetaCompliance Special Edition of Cyber Security Awareness For Dummies.
- Received a 2025 North West Regional College honorary award recognising contribution to the economy.

## Latest updates

- **2026-11** — Scheduled to speak at the European Digital Governance Summit on 25 November 2026; this is a forthcoming appearance as of 23 October 2026.
- **2026-09** — The Cybersecurity CEO Podcast published a conversation with Hexagon’s Steve Lorimer about security priorities and leadership.
- **2026-06** — Published an introductory Substack essay discussing his business background and work on a book for senior leaders.
- **2026-04** — Safe Harbour Security announced finalist places in two NI Cyber Community Awards categories; the announcement identifies him as chairman and co-founder.
- **2026-02** — Warned publicly about AI-enabled cybercrime affecting SMEs and promoted practical security briefings.

## Links

- Website: https://cybersecurityceo.substack.com/
- LinkedIn: https://www.linkedin.com/in/thecyberceo/
- YouTube: https://www.youtube.com/@TheCyberCEO

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Profile page: https://yespress.io/robbie-obrien
Published by YesPress — https://yespress.io
Last updated: 2026-10-23