Upon graduation from Northern Illinois University he returned home and worked for two years at the Liberian Development Bank, until the tail-end of the 1980s.

Cummings led a period of strong growth in Coca-Cola's Africa business, overseeing critical investments in marketing and infrastructure across 56 African countries and territories from 2001 to 2008.

He previously served as a Board Member of the Africa-America Institute, Chevron, Africare, the Corporate Council on Africa, and the US-Egypt Business Council, on the Advisory Board at The African Presidential Archives & Research Center and on the Center for Global Development's Commission on US Policy toward Low-Income Poorly Performing States (LIPPS),Sabathani Community Center in Minneapolis, MN, USA[5] He also served as an Independent Director of Chevron Corporation from 10 December 2014 until 27 April 2016, and as a Director of International Bank (Liberia) Limited.

Cummings has a long history of philanthropy and supporting his home country Liberia, globally; supporting funding for water projects and providing students scholarships in Liberia, and donating to various causes including the African Methodist Episcopal University's Innovation Center named in his honour.

[7] In 2011, President Ellen Johnson Sirleaf conferred on Mr. Cummings the distinction of Knight Great Band – Humane Order of African Redemption; the medal is one of the highest honours in Liberia and is awarded for humanitarian work in Liberia, for acts supporting and assisting the Liberian nation.

In 2001, the Foundation established an extensive healthcare program for Coca-Cola workers affected by HIV/AIDS and related conditions across Africa in addition to supporting HIV/AIDS prevention and awareness throughout local communities.

The Cummings Foundation focuses on empowering and uplifting Africans in health, education, agriculture, and the arts.

Since its formation, the foundation has invested over one million U.S. dollars in projects in Africa, including facilitating the construction of a STEM (Science, Technology, Engineering and Mathematics) academic institution, the first of its kind in Liberia.