Ollis joined the Democratic Party in 1998 and served in its various formations, including the 1999 parliamentary election campaign, before being elected to the City Council of Johannesburg for the renamed DA in 2005 and then re-elected as a ward councillor in 2006. He has worked in the party's fundraising department and served on the Gauteng South Regional executive. In 2009, Ollis was elected a member of Parliament and currently serves as the party's Shadow Minister of Labour, the political head of the Sandton Constituency and was the Deputy Chairman of the Gauteng Executive of the DA. In October 2010, Ollis submitted a Private Members' Bill that would hold unions accountable for violence and damage to property caused during strikes. On 15 November 2011, the Department of Labour announced that amendments would be made to the corresponding Act, in a proposal similar to the DA's. Throughout his term as Shadow Labour Minister, Ollis has been at the forefront of the quest to reduce endemic unemployment in South Africa. In February 2011, Ollis issued a statement on the proposed amendments to the Employment Equity Act, citing that the legislative changes would be unconstitutional and create "massive problems" if implemented. In October 2011, Ollis submitted a private member's bill to amend the Compensation for Occupational Injuries and Diseases Act to expand the Compensation Fund's coverage to include domestic workers. From 1 February 2012 until April 2014, Ian Ollis served as the Shadow Transport Minister in the Parliament of South Africa. He drafted the Democratic Alliance's new Transportation Policy approved in November 2013.
Mid-Career Study Sabbatical
In August 2018 Ollis resigned his seat in Parliament to complete a second master's degree at the Massachusetts Institute of Technology. He completed a Masters in City Planning degree with a Transportation Specialization in May 2020. During the US summer of 2019 Ollis took up a summer internship at the Pioneer Institute, a research and policy institution in Boston, writing and publishing detailed policy papers for the Institute. He completed the degree in May 2020. His Master's thesis entitled: "Alleviating Carmageddon with a research-driven Rapid Transit approach" included a survey of motorists on the most congested roads in Massachusetts. An article was published discussing it in Commonwealth Magazine entitled: "Avoiding a return to carmageddon" June 18, 2020 https://commonwealthmagazine.org/opinion/avoiding-a-return-to-carmageddon/
