Jordan O’Reilly used to give new employees a rather economical introduction to Hireup. He pointed out the toilets, identified the kitchen and invited people to shout if they needed anything. Then came the instruction: “now let's do this!!” Corporate orientation, stripped to its plumbing. There was work to get on with, and apparently no pressing need for a commemorative lanyard.
By October 2021, the welcome had acquired a name, Launchpad, and a monthly session with roughly 20 recruits. O’Reilly still ran it. He wrote that he had personally inducted everyone employed at the central support office. That week, support workers joined the group of permanent employees for the first time. One, Michelle, told him that a mortgage broker had previously ruled out a home loan because her work lacked permanency.
For a technology founder, this was an unusually concrete measure of progress. A change in an employment arrangement might alter what someone could plan for outside work. It made visible a conviction running through O’Reilly’s career: the organisation behind a screen matters as much as the screen. His choices about that organisation would become the most interesting argument his business made.
A computer business before a platform
Long before Hireup had staff inductions, O’Reilly’s younger brother Shane had a business idea. He wanted a career in IT and offered to repair neighbours’ computers under the name Shane The Computer Man. The enterprise was small. The ambition was entirely recognisable: to be useful, earn money and have somewhere to direct a talent.
Jordan remembered a different reception when the family secured Shane an internship. He spent an entire day licking envelopes. It is a detail with a particularly sour economy: a young person who wanted to work with computers was given a task that took no interest in that ability. In 2020, Jordan returned to the episode while explaining why employment mattered to him.
The O’Reilly household had expected participation from everyone. Jordan, Laura and Shane played games, played pranks and argued. Inclusion extended to chores. Outside the family, however, opportunities could be much more narrowly prescribed. Jordan and Laura encountered arrangements in which someone else decided who would arrive to provide support, with little room for the relationships and shared interests that made an ordinary day enjoyable.
That distinction gave their eventual business a starting point. They had seen the difference a good personal match could make. They also knew the frustration of having little say in finding one. Jordan’s later work would keep returning to the question of who gets to make that decision.
Three founders, one practical question
In 2011, Jordan and Laura co-founded Fighting Chance. The organisation developed social enterprises around employment and participation. Jordan was still at the University of Sydney, where he also worked as a support worker. He was getting two views of the same arrangements: the family trying to find the right person, and the worker trying to do a useful job.
Hireup followed in 2015. Its founding team included the siblings and Murray Bunton, a detail that matters in a story often told as a family double act. Making a personal frustration into a working platform required more than the original insight. It required a team capable of building something people could actually use.
The proposition was straightforward. People could search for support workers, choose someone whose experience and interests suited them, and manage the relationship online. Common ground had practical value. Someone’s enthusiasm for music or sport could help determine whether time spent together felt easy, interesting and worth repeating.
Explaining the origins in 2022, Jordan wrote: “We learned that the best way to get great support was to find it ourselves.” The useful word is “ourselves”. Hireup put a decision closer to the person whose life it affected. The technology made that choice easier to organise.
The employer behind the app
O’Reilly was repeatedly advised that the platform should use independent contractors. That was a familiar route for a business matching people online. He chose direct employment. Hireup would take responsibility for the workers using its platform, including payroll, superannuation and the entitlements attached to employment.
The choice created a business with two promises to keep. Customers wanted autonomy over their support. Workers wanted flexibility and proper conditions. Those interests had to coexist in the same operating model, with the company doing the administrative work that made the arrangement possible. A pleasing interface could only handle part of the job.
At a Senate hearing in April 2021, O’Reilly challenged the suggestion that a platform needed contractors to deliver flexibility. His conclusion was brisk: “I would say that we need to try harder.” It was a founder’s argument made in the language of responsibility. Other companies’ choices did not settle what his own company could attempt.
He continued making that case publicly. In 2022, he warned about workers losing entitlements as more work moved through platforms. In August 2023, he appeared in the national debate about workplace protections. The subject had taken him beyond the familiar founder circuit of product launches and fundraising announcements, into arguments about how an industry should organise work.
There is a cost to accepting the responsibilities of an employer, and O’Reilly acknowledged the competitive pressure of operating alongside businesses with different arrangements. That tension gives the story substance. His position was embedded in the company’s obligations, where it could be tested every pay cycle.
“I would say that we need to try harder.”
Jordan O’Reilly · Senate testimony, April 2021
Growth, with people still attached
Hireup won Deloitte’s Australian Technology Fast 50 in 2017. When O’Reilly discussed the award the following year, he emphasised the conversations it opened: with prospective employees, platform users and government. Recognition helped people discover a service they might otherwise never have encountered. The trophy had acquired a job in recruitment and introductions.
Other honours followed. Jordan and Laura jointly received the 2021 NSW Pearcey Entrepreneur of the Year award. In June 2023, Jordan received the Medal of the Order of Australia for service to the disability sector. The honours trace the range of audiences paying attention to his work, from technology circles to the wider public.
The internal measures grew too. Hireup’s anniversary account records its first 10,000 hours of support in 2016 and one million hours in 2018. Those numbers describe accumulated time spent working together. A marketplace can count registrations; hours offer another way to see whether people are actually using what has been built.
O’Reilly also wanted the office itself to offer opportunities. In 2020, he described an accessible headquarters with more than 200 staff and launched an initiative called Employment for All. It aimed to increase employment of people with disability through training, recruitment and changes inside the organisation. The promise was personal, reaching back to Shane’s ambitions.
A founder who argues for choice has to allow other people to influence the business. Hireup’s later development included a community advisory group bringing clients, account managers and support workers into discussions about projects. Its internship partnership with Jigsaw began in May 2023. These are practical ways of letting people participate in decisions and work, beyond appearing in a company’s account of its purpose.
Seven hundred and fifty kilometres away
After years spent building Fighting Chance and Hireup, O’Reilly took time off in 2025. His account of the break contains the sort of details usually absent from an executive biography: 750 kilometres of cycling along Ireland’s Wild Atlantic Way, walking in Wales and an engagement on a hillside in North Yorkshire. He described the Yorkshire location as spiritually significant for his family.
It is a useful interruption in a career otherwise easy to compress into founding dates and awards. The bicycle trip gives the period a scale of its own, measured in kilometres rather than people employed. His return-to-Sydney message was cheerful and practical. There were projects to resume and people to reconnect with.
One of those projects was a Churchill Fellowship examining digital government. The research focused on how technology could make publicly funded systems more efficient and fair. He had spent years working within the rules of a system; now he was making room to study how the rules and their digital machinery might work better together.
Back in class, back at the beginning
In 2026, O’Reilly’s next classroom was Harvard Kennedy School. Selected as a John and Anna Belfer Trust John Monash Scholar, he began a mid-career Master in Public Administration. His studies bring technology and entrepreneurship into conversation with public policy. The course represents a change of setting for a question he has been carrying for years.
He is also building Evenn, a govtech platform concerned with self-directed support and the administration of personalised funding. Its stated ambition reaches beyond Australia. The work takes the problem further into the machinery of government: how individuals navigate funding, and how public bodies administer it. It remains a developing venture, with an ambition to demonstrate.
Returning to study after running a company has a certain appeal. Experience supplies plenty of answers, along with a rather better list of questions. O’Reilly has seen a family’s frustration become a product, an employment policy become a public argument, and an office welcome become a conversation about someone’s prospects of buying a home.
The thread connecting those episodes is remarkably ordinary. People want a say in their day, a chance to use their abilities and enough certainty to plan ahead. Jordan O’Reilly has spent his working life trying to organise businesses around those wishes. At Harvard, and with another platform taking shape, he is still working out how much more of the system can be persuaded to cooperate.