[4] Hailer began his career at Fidelity Investments in 1986, selling corporate cash products, retirement plans and pension fund management services.

In 2007 Hailer was named president and chief executive officer of Natixis Global Asset Management (NGAM) – The Americas & Asia.

[9] He was responsible for NGAM's distribution strategies worldwide and oversaw the business activities of the firm's asset management affiliates in the United States and Asia.

[28] He is a former chair of the board of directors of The Home for Little Wanderers, the oldest continuously operated children's charity in the United States.

Hailer is also responsible for creating an Adopt-A-School Program in partnership with the City of Boston and the John Winthrop Elementary School in Dorchester.

[36] Natixis and Hailer were the 2014 Presenting Sponsors of the Newport Jazz Festival and the 2014 Berklee College Summer Music Series.

[39] Also in 2013, Hailer was recognized by The Home for Little Wanderers, having helped to raise more than $23 million, build a new campus for the foundation in Walpole, and open additional facilities in Plymouth and Roxbury.