He joined as a second lieutenant, rising to the rank of captain, and was stationed at Camp Lejeune in Jacksonville, North Carolina, where he worked on computer systems.

In 1994, he joined Morgan Stanley as an enterprise software-industry analyst in the investment banking technology group,[9][10] and he was promoted to managing director, a role in which he served through 2003.

Phillips spent his time on Wall Street nurturing relationships with hedge funders, venture capitalists, private equity executives, technology CEOs, and other business and financial leaders, and gained a reputation for being one of the most aggressive, connected, influential, and prolific technology investment analysts.

[6][11] Institutional Investor ranked him the number one Enterprise Software Industry Analyst for ten consecutive years, from 1994 to 2003.

[3] Responsible for Oracle's sales and acquisitions, he utilized his networking, negotiation, and closing skills,[6] and became one of the highest-profile African-Americans in the technology industry in the mid 2000s.

[19] In October 2011, Phillips moved Infor's headquarters from the Atlanta suburb of Alpharetta, Georgia to New York City's Silicon Alley.

[6][20] He immediately set about re-directing Infor and its efforts,[21] instilling a corporate culture of camaraderie, goodwill, and reward.

He refocused Infor towards enhanced product integration,[21][27] and to custom-creating and fine-tuning software for the specific needs of individual industries.

[29][31][36][37] In 2014 Infor also launched Dynamic Science Labs, located in Kendall Square on the Massachusetts Institute of Technology (MIT) campus, where a team of more than 70 PhD-level scientists develop applications for predictive analytics, machine learning, managing retail assortments, optimizing inventory, and planning segmented pricing for customers.

[58] In 2016 Infor's in-house design agency that Phillips created in 2012, Hook & Loop, expanded to launch H&L Digital, which offers "digital-as-a service",[59] working directly with customers to create end-to-end digital cloud solutions[buzzword] by strategizing, designing, assembling, and running client-specific software.

[64][65][66] Coleman AI allows Infor to leverage business data captured by its applications to provide predictive analytics, optimizations, industry benchmarks, and correlations;[67] it was launched in 2018.

[68] To develop more talent for the company, in 2014 he instituted Infor's Education Alliance Program, sponsoring courses at higher-education institutions which offer certifications on Infor's software suites plus opportunities for internships and other trainings that help students develop skills for careers in the tech industry.

[71] Under Phillips' leadership, by 2018 Infor became the first ERP provider to make a complete transition to the cloud,[72][73] utilizing a model of multi-tenant, industry-specific software as a service (SaaS) CloudSuites.

[73][81] In late 2018, Phillips led Infor to team with #YesWeCode to form GenOne, an initiative to increase the diversity of the tech workforce.

[86] He is on the board of directors of Business Executives for National Security (BENS),[87] the Posse Foundation,[88][5][89] and the United States Air Force Academy Endowment.

[97][98] Phillips is on the International Advisory Board of Banco Santander,[99] and he has been a Class B Director of the Federal Reserve Bank of New York since January 2018.

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