James Mackay

Chief Executive Officer MetaCompliance

Last Reviewed: September 28, 2026

Executive Summary

James Mackay is Chief Executive Officer of MetaCompliance, the company headquartered in Derry/Londonderry that sells security awareness training, phishing simulation and compliance software, and now describes itself as a human risk management company. He took over as CEO in October 2023 from Robert O’Brien, who remained on the board as Chief Evangelist, having spent seven years at the business and served as its Chief Operating Officer. His tenure has been defined by consolidation and a change of backer: MetaCompliance moved from Tenzing to Keensight Capital, and under him it has bought companies in Germany and the Nordics to build a larger European footprint.

Career Highlights

• Chief Executive Officer of MetaCompliance since October 2023, succeeding Robert O’Brien.
• Previously Chief Operating Officer of MetaCompliance, with seven years at the company by the time of his appointment as CEO.
• A director of MetaCompliance Limited since November 2017 and its company secretary since January 2018, according to Companies House.
• Led the business as Keensight Capital agreed in December 2024 to acquire a majority stake from Tenzing.
• Oversaw the acquisitions of Increase Your Skills (IYS) of Leipzig in November 2023 and Junglemap, a Nordic security and compliance awareness provider, in December 2025.

Professional Journey

Mackay built his career at MetaCompliance inside the business before running it. Companies House records him as a director of MetaCompliance Limited from 1 November 2017 and as company secretary from 1 January 2018, and by 2023 he was Chief Operating Officer. The company had been built over nearly two decades by Robert O’Brien into a provider of policy management, eLearning, simulated phishing and compliance tools used by public and private sector organisations. In January 2021 the London private equity firm Tenzing invested, and with its support MetaCompliance bought MOCH of Copenhagen in 2022.

In October 2023 MetaCompliance announced that Mackay would become Chief Executive Officer with immediate effect, with O’Brien continuing as a board member and Chief Evangelist. The company said Mackay would lead its message of personalised security awareness and guide its scaling and global go-to-market strategy. “I am honoured to assume the role of CEO and lead MetaCompliance into its next phase of growth,” he said. Weeks later the company completed the acquisition of Increase Your Skills GmbH, a Leipzig security awareness business with public sector customers and AI-driven phishing simulation, to strengthen its position in the German-speaking market.

In December 2024 MetaCompliance announced that Keensight Capital, the European growth buyout firm, had signed an exclusivity agreement to acquire a majority stake. The company said it had more than doubled in size over the previous three years to over 200 employees, with an offshore development centre in Portugal. Mackay thanked Tenzing for a partnership that had been “pivotal” and said that with Keensight the company was “excited to accelerate our mission and take the business to the next level”.

With Keensight’s support, MetaCompliance acquired Junglemap in December 2025. Junglemap, founded in 2002 with offices in Stockholm and Oslo, serves about 1,200 customers across the Nordics and Benelux with its NanoLearning approach, and the deal gave MetaCompliance a Nordic hub spanning Sweden, Norway and Denmark. The company called it its third acquisition in three years. Mackay described it as “an important step in our European growth journey”.

Education

No education record was found in any source read for this profile.