Disability Trust chief executive Margaret Bowen won the 2014 NSW Telstra Business Women's Community and Government Award in Sydney on Friday night.
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Mrs Bowen was the third Wollongong resident to win such recognition in the past decade, but the first in eight years.
The last Wollongong winner was Dr Jennifer Smiley in 2006.
That came a year after Professor Julie Steele took out the same category Ms Bowen did on Friday.
The citation read of how, after 27 years in the one job, the Disability Trust CEO remained energised and kept reinventing herself and the organisation.
The judges noted her passion for social justice and inclusive communities and were impressed with how she had overseen the not-for-profit's growth from a disability advocacy organisation with four staff to a service-providing sector leader employing more than 1000 people with a turnover of $75 million.
Along the way, she also changed the Disability Trust's business model to become more self-reliant.
The judges also praised her pride in her industry and profession and the social enterprise model she'd introduced in care, fitness and travel programs.
In December 2006, Dr Smiley went on from winning at the state level to achieve a first for the Illawarra when she was recognised as Australia's best businesswoman in the corporate and private sector.
Not only was she recognised for being the founder of a family medical practice, but her roles as chairperson of the after-hours Wollongong Medical Service and the Cervical Screening Working Group, which aimed to register women from non-English speaking and disadvantaged backgrounds for screening.
And she helped develop similar resources for breast-cancer screening around Australia.
It was noted how she helped turn the Wollongong Medical Service's after-hours medical provider's Radio Doctor service around when it was losing money and in danger of disappearing.
She implemented new business practices, better patient care and shorter response times.
The year before, Professor Steele, who heads the University of Wollongong's Biomechanics Research Laboratory, was recognised for becoming one of Australia's most eminent researchers in the field of applied biomechanics.
She has also commercialised the sport bra, among others.