In this capacity, he is responsible for shaping strategies to attract foreign direct investment and foster economic growth in the Greater Toronto Region.

He resigned from that role in 2020, after he took a vacation to St. Barts contrary to his government's public health advice during the COVID-19 pandemic, but was later named the minister of long-term care in 2021.

[5] In 2001, after stint working as chief of staff to the mayor of Toronto, Mel Lastman, Phillips became co-managing director of the venture division of Goodmans LLP, one of Canada's leading law firms.

[6] In 2002, Phillips became president and CEO of Shepell-fgi, a company that delivered workplace health and productivity solutions to eight million employees and family members from over 7,000 organizations in Canada and 54 other countries.

Under Phillips's leadership, Shepell-fgi (now Morneau-Shepell) grew its services to include elder and child support, legal advice, financial guidance, and help with mental health and addiction issues.

[8] During his tenure at OLG, Phillips led an effort to rehabilitate its reputation following several widely publicized scandals involving theft of winning tickets and fraudulently claimed prizes.

Phillips led the corporation to its highest net profit since 2005 and oversaw the design and launch of the modernization of Ontario's lottery and gaming industry.

[9] Under Phillips's direction, OLG was praised after it was able to identify a $50 million lottery winner, Kathy Jones, who had lost her winning ticket.

[10] After leaving OLG, Phillips became the chair of the board of Postmedia, Canada's largest news media company, whose portfolio includes the National Post, the Toronto Sun, and the Ottawa Citizen.

[12][13] Phillips worked as chief of staff for former Ontario PC cabinet minister Elizabeth Witmer and former mayor of Toronto Mel Lastman.

[citation needed] Phillips considered running in the 2018 Progressive Conservative Party of Ontario leadership election, but ultimately declined and backed Caroline Mulroney.

[36] Phillips served as volunteer chair (2014–2017) of CivicAction a non-profit which focuses on issues in the Greater Toronto and Hamilton Area (GTHA).

[37][38] Phillips supported the CivicAction DiverseCity Fellows program, which seeks to have Toronto's leadership more fully reflect the city's cultural diversity.