Annrai O’Toole’s start-up Utmost raises €11.2m

Enterprise software company Utmost – which was co-founded by Iona and Cape Clear co-founder Annrai O’Toole – has raised €11.2m in a Series A round.

Utmost is building solutions for the enterprise and its extended workforce – from temporary workers to consultants, vendors, freelancers, contractors and more – to seamlessly and efficiently work together.

The software is designed with extended workers in mind, enabling them to have control of their data and transparency into their work history, independent of traditional employment relationships.

“Annrai, Dan, and Paddy are a customer-centric and experienced team of technologists uniquely poised to tackle this growing shift in the way people work”

Almost 80pc of chief human resource officers see a greater use of contingent non-traditional employees as one solution to future worker and skill shortages, according to the C-Suite Challenge 2018 Survey from The Conference Board. In addition, Staffing Industry Analysts estimates total global spend for the non-traditional workforce reached $4.5trn in 2018. Despite this growing demand, Deloitte’s 2019 Human Capital Trends report estimates that less than one in 12 enterprises have established processes to manage this population.

The return of the high king of Irish software

Three men smiling in front of a grey background.

Pictured (left to right): Utmost COO Dan Beck, CEO Annrai O’Toole and CTO Paddy Benson.

Annrai O’Toole was a co-founder of Iona Technologies, the second Irish company ever to go public on the Nasdaq in 1997. He then created another successful start-up, Cape Clear, which was acquired by Workday in 2008

“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,” O’Toole said. ]

“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.”

Greylock Partners has previously worked with O’Toole as an early investor in Cape Clear. Sarah Guo and Saam Motamedi from Greylock Partners sit on the board of Utmost along with Mike Stankey, vice chairman at Workday.

“Annrai, Dan, and Paddy are a customer-centric and experienced team of technologists uniquely poised to tackle this growing shift in the way people work,” said Guo.

“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.”

Main image: Utmost staff with Annrai O’Toole standing in the centre in white shirt.

Written by John Kennedy (

Published: 9 October, 2019