When Borders was unable to obtain the necessary federal regulatory approval in Canada, Reisman founded a company called Indigo Books and Music.

[5] Although Indigo has increasingly stocked giftware in its stores, Reisman said this in a 2018 interview about the company's core product: "Books were, are, and always will be the heart and soul of our business".

[10] She drew praise and criticism in October 2001 after announcing that Indigo would not sell Hitler's Mein Kampf in its bookstores.

[11][12] On July 5, 2010, Reisman launched an online petition to save an Iranian woman, Sakineh Ashtiani, from the death penalty by stoning.

Heather Reisman is the co-founder of the HESEG Foundation for Lone Soldiers alongside her husband, Gerald Schwartz.

Every year, the organization provides millions of dollars worth of support to former "lone soliders" who have recently served in the Israeli military.

[17] Protestors have cited that HESEG – which enjoys the significant tax benefits associated with holding charitable status in Canada – provides support for the soldiers of a state that is currently on trial for genocide in the International Court of Justice.

[18] In 2006, Reisman founded the Indigo Love of Reading Foundation, whose mission is to enrich the libraries in under-resourced public schools.

[19] In 2005, she and her husband Gerald Schwartz founded the HESEG Foundation, which provides scholarships to former Israeli "lone soldiers."

Mount Sinai Hospital announced in December 2013 that a $15 million gift from Reisman and Schwartz would be used to "reshape emergency medicine" at the facility.

[20][21] The Gerald Schwartz and Heather Reisman Foundation donated $5.3 million to St. Francis Xavier University in Antigonish, Nova Scotia in late 2018 to create scholarships, bursaries and increased recruitment of business students.

[36] Her father, Mark, was a real estate developer; her mother, Rose, owned a clothing store; and her brother, Howard, founded computer company Time Systems.