Shirley-May started her career at KPMG in Los Angeles. She was an active CPA for 10 years and went on to build the consulting arm of Parker & Lynch in San Francisco- here she partnered with CFOs and Founders on internal strategic initiatives such as IPO readiness, financial system implementations/ migrations, and stop gap leadership solutions.

In 2015 Shirley-May joined Uber Technologies, focusing on recruiting leadership in the finance organization. When she left Uber in late 2018 she was manging a large team and leading all recruiting efforts for finance, legal, policy and communications teams for North America. During this time Uber grew from less than 3k employees to 25k employees.

Shirley then moved on to leading talent at Sonder and Gusto. Her last role at Gusto was advising engineering, product, and design leadership on all HR matters from employee performance and talent planning to integrating teams from mergers and acquisitions.