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A Total Life and Career Transformation and Two Chance Encounters helped Anne Fitzgerald, Chief Legal Officer at Cineplex find her dream job

Anne Fitzgerald, Chief Legal Officer at Canada’s largest motion picture distributor, Cineplex, rose to her recent starring role by embracing chance encounters.

By: Larysa Pachulski | Photo: Kourosh Keshiri


As a member of the elite 23 percent of women who hold senior executive positions in Canada, perhaps the most impressive thing about Fitzgerald is her past: marked with detours, fresh starts and, ultimately, personal enlightenment.

Fitzgerald began her career in law in a rather conventional way. She started out in her hometown of Raleigh, North Carolina, as a corporate commercial litigator in a large firm who worked predominantly as a desk jockey, reviewing documents and performing legal research. In her personal life she had also chosen a rather safe route, marrying her college sweetheart at the tender age of 20. From the outside, it seemed that Fitzgerald was living an idyllic life, but when asked about those years she admits, “[I was] sleepwalking through life.”

As is often the case in the lives of those destined for bigger things, fate stepped in as Fitzgerald was abruptly awakened by a pivotal conversation with her then brother-in-law. Unfortunately, in order to free herself up to all of the new opportunities swift change would allow her, Fitzgerald would have to free herself from her husband first. But the possibility of rebirth altered the waves of her brain and opened up her mind to new and drastically different ideas. There was no going back. And just like that, Fitzgerald rejected convention and the idyllic façade was history.

If there is one aspect of Fitzgerald’s character that has emerged most often throughout her past, it is her refusal to do anything half way, including change. True to form, Fitzgerald sent shock waves through her family and friends when she announced her plan to leave her hometown, her husband and her steady job for the icy outdoors of Alaska, in order to head a youth leadership expedition.

Fitzgerald would surprise her friends and family twice more with her abrupt embrace of total personal transformation, in order to end up where she is today. She’s worked all over the United States, as a litigator for a large firm, an expedition leader and a criminal prosecutor in several serious criminal cases with national exposure.

One day, through a chance encounter with an old college professor, Fitzgerald landed the opportunity to teach leadership to Duke University seniors in the glamorous setting of New York, using the city’s renowned arts scene as a backdrop for her lessons. Coming from a stint in a small military town, she discovered a love of city life and was able to explore her passion.

Fitzgerald finally settled in, but “nothing lasts forever,” she says.

It was a blind date with a Canadian man that led to the next big transformation in her life. One year later, Fitzgerald was remarried and headed for the city of Toronto. Successful in love, Fitzgerald now had A the task of finding employment in her new home, and this time, the position would not simply fall into her lap by happenstance.

Forced into an 18-month unemployment stretch due to the lag time during which her Canadian work permit was being processed, she would have for the first time, the opportunity to forge her own way. Not all of us get the opportunity to put our lives on hold in order to examine and eke out our dream occupation, but there are applicable lessons to be learned from Fitzgerald’s personal experience.

Under the guidance of a professional consultant – a resource she highly recommends – Fitzgerald discovered that her passion was to combine all of her skills to be an in-house corporate/ commercial lawyer in an entertainment setting.

She knew her past work in corporate law was well behind her, so finding a job would not be a simple endeavour. Fitzgerald also knew that 90 percent of all senior level jobs in North America are found through networking.

“Networking is planned, purposeful and ongoing…it is not mainpulative or asking for a job.”

Through a series of networking engagements, Fitzgerald was introduced to countless individuals connected to her chosen field. She eventually met with someone from Cineplex, the largest motion picture exhibitor in Canada, which now owns, leases or has a joint-venture interest in 134 theatres, serving approximately 70 million guests annually. Founded in 1979 with the opening of its first theatre, a 21-screen megaplex at Toronto’s Eaton Centre, the company quickly expanded to Los Angeles, Chicago, New York, Washington DC and Seattle.

Fitzgerald found not only was there no opening for in-house counsel – surprisingly, Cineplex did not even use in-house counsel. In a prescient move, she instead netted herself a couple contract jobs with the entertainment company, eventually leading to a key role in Cineplex’s acquisition of Famous Players. It was through these temporary jobs that she cultivated a relationship and a trust amongst the senior staff. On her proven merit, the executives of Cineplex were influenced into creating an in-house counsel position, which Fitzgerald has managed, developed and expanded ever since.

It’s become an idyllic life once more; she has found love in her life and she is in love with her career.

When asked how her current position engages and challenges her from day to day, Fitzgerald explains that as the protector of the integrity of Cineplex, she is involved in every aspect of company. “The legal team supports every department within the company, each doing something exciting and new, and we support all of those initiatives.”

She no longer feels the need to escape and drastically alter her life, because the nature of her work is already so challenging and diverse; she deals with transformation every day. However, one thing does continue to change regularly for Fitzgerald, and that is her favourite movie. “This week, it’s ‘The Usual Suspects’,” she says with a grin.

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Click here to watch the video of Anne Fitzgerald’s inspiring speech at her November 2012 Young Women of Influence event “Negotiating Blockbuster Deals”.