Irish tech veteran Annrai O’Toole raises further $21m for his start-up

Utmost, a company with a HR-focused software solution, had already raised $11.2m

Utmost, a company co-founded by Irish tech veteran Annrai O'Toole, has secured $21 million (€17.5 million) in a Series B funding round.

This brings to $32.2 million the total money raised by the start-up, which was founded in late 2018.

Utmost has developed a software solution called the Extended Workforce System that helps HR teams manage individuals who work for but are not directly employed by companies. This include contractors, freelancers, vendors and consultants.

“In 2000 a mere 10 per cent of the workforce could be classified as “extended workers,” today, that number exceeds 43 per cent, and we are rapidly reaching the point where a majority of the workforce will be “extended.” The future of work belongs to the non-employees,” said Mr O’Toole.


Mr O’Toole said Utmost, whose products are used by Fortune 500 companies, had recorded a 150 per cent rise in customers last year. He said the company has built on this further in 2021 with “workers under management” growing over 90 per cent to just over 70,000 in the first quarter.

“As we enter this next chapter in our journey, we look forward to building out Utmost to fulfil all the hopes and dreams we have for our product. We will continue to make our existing customers successful and aim to serve many more customers,” said the entrepreneur.

Mr O'Toole is well-known in tech circles as the co-founder of both Iona Technologies and Cape Clear Software. The latter company was acquired by Workday in 2008, and Mr O'Toole ran the Irish operation in subsequent years.

The other co-founders of Utmost are former Workday executive Dan Beck and former Groupon chief technology officer Paddy Benson.

Mosaic Ventures, which last year led an $18 million fundraise for Cork-based AI supply chain company Keelvar, led the latest funding round. It is a London-based VC, whose founders led early investments in companies including Alibaba, Etsy, Indiegogo and Pinterest.

Other backers of the company include Silicon Valley-based Greylock Partners, which has previously backed the likes of Airbnb and Coinbase, and Workday Ventures, the $250 million investment arm of Mr O’Toole’s former employer.

Charlie Taylor

Charlie Taylor

Charlie Taylor is a former Irish Times business journalist