Irish tech veteran Annrai O’Toole secures $11.2m for new venture

Utmost has developed a solution to manage workers not directly employed by companies

Utmost, a company co-founded by Irish tech veteran Annrai O’Toole, has raised $11.2 million (€10.2 million) ahead of the release of its new HR-focused software.

Silicon Valley-based Greylock Partners, which has previously backed the likes of Airbnb, Coinbase, Gofundme, Next Door and Medium, led the series A fund-raising round. Workday Ventures, the $250 million investment arm of Mr O'Toole's former employer Workday, also participated in the latest fundraising round.

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, which was established last year, are former Workday executive Dan Beck and former Groupon chief technology officer Paddy Benson.


The start-up, which has offices in Dublin and San Francisco, is about to release a new solution known as Utmost Extended Workforce. This is a product that helps manage individuals who work for but are not directly employed by companies. This include contractors, freelancers, vendors and consultants.

Undeniable shift

“With hundreds of millions of extended workers engaged with companies today, there is an undeniable shift happening, yet it is clear that businesses need new, seamless solutions to transparently manage this population,” said Mr O’Toole, the company’s chief executive.

“We want to make a difference – we are leading the charge by creating the first software system that helps companies and the extended workforce work together,” he added.

Greylock was an early investor in Cape Clear, which Mr O’Toole founded in 1999 along with other senior Iona executives after leaving the company.

Iona, a Trinity College Dublin spinout that was founded in 1991, was acquired by Progress Software in 2008 for a reported $162 million, was one of Ireland's most successful technology companies, floating on the Nasdaq stock exchange in 1997 and at one stage valued at $1.75 billion.

"Companies in every sector engage with an extended workforce, but the rigid and clunky systems used to manage that workforce are stuck in the past. Utmost is a cloud solution for the modern, flexible enterprise, and offers a worker-centric approach to manage this population that enterprises previously lacked," said Sarah Guo, a partner at Greylock.

Charlie Taylor

Charlie Taylor

Charlie Taylor is a former Irish Times business journalist