Currently a Senior Advisor on Legal and and Constitutional Affairs at the reconstituted Joint Monitoring and Evaluation Commission (RJMEC) overseeing the implementation of the Agreement on the Resolution of the Conflict in the Republic of South Sudan.

Oola is also the founder and director of Amani Institute Uganda, a think-tank based in Gulu, northern Uganda. Oola is an Advocate (Attorney) in the High Court of Uganda.

Between 2013 and 2016, Oola was head of the Conflict, Transitional Justice and Governance Program at the Refugee Law Project (RLP), School of Law, Makerere University in Kampala. Previously, he led the Research and Advocacy Department at RLP from 2010-2012 and conducted a countrywide reconciliation and transitional justice audit in Uganda (2011-2012).

From 2007-2009, Oola was the Transitional Justice Lawyer at RLP. In 2008, Oola drafted a proposed National Reconciliation Bill for Uganda. In 2010, he proposed and drafted the first text of the African Transitional Justice Policy Framework (AUTJF).

Between 2007-2018 he was member of the South Sudanese High-Level Revitalisation Forum Taskforce and Legal Advisor to the IGAD Mediation team, and lead drafter of the Revitalised Agreement on the Resolution of the Conflict in the Republic of South Sudan, signed September 2018.