Course Correction

At age 29, Deborah Greenberg left the marketing world to enter law school, and today she’s helping Aimia, a top loyalty-management company born from Air Canada, grow and expand its footprint

Deborah Greenberg, VP and general counsel.

Deborah Greenberg started at Davies Ward Philips & Vineberg LLP and left private practice after seven years to serve as a legal advisor for various small businesses. Then, after advising Air Canada, she joined Aeroplan in 2007, and today she serves as vice president and general counsel in Canada for Aeroplan’s parent company, Aimia Inc., a global leader in loyalty management.

It would be an impressive résumé for any lawyer, but Greenberg’s accomplishments are especially noteworthy considering one fact: law is her second career.

Although she was raised in a family of lawyers and judges and was encouraged to follow in their footsteps, Greenberg first obtained degrees in psychology and graduate management. From 1987 to 1995, she held various positions in marketing and advertising, and she even spent many years as the director of marketing for a private-label health and beauty manufacturer, where she researched trends, developed products, priced raw materials, led customer service, and managed quality control. Professionally, she was doing well, but something was missing. “I never really achieved the job satisfaction I was looking for,” she says. “I always had this deep need for something more.”


“It’s not good enough for me to show up and like something. I have to love it. When I finally went to law school, I realized on day one that I loved the intellectual challenge and critical thinking. I knew I made the right choice, and I haven’t looked back.”

That longing led Greenberg to give in to her family’s prodding and enter law school. Even as she did so, though, she wasn’t quite sure about it until she actually stepped into the lecture hall. “I was at a crossroads in my life and was 10 years older than all of my classmates,” she says. “Once I started, I instantly loved the logic and intellectual stimulation of it all.”

The younger students saw law school as a means to an end, but for Greenberg, it was a career choice. Upon graduation, she started working for a prestigious firm and learned many aspects of securities law, commercial law, privacy law, and mergers and acquisitions. After seven years, though, she still felt disconnected. “I had loved law school but didn’t love my job,” she says. “I knew I still hadn’t arrived.”

Greenberg left her firm and spent several years consulting before she eventually took a position at Air Canada. That’s when she finally had what she describes as her “aha moment.” The airline’s legal department handled all work for company subsidiaries, including Aeroplan, which meant Greenberg was negotiating partnerships, writing agreements, and assisting in marketing. “My legal and marketing worlds collided,” she says. “I knew that I had found the right role for me.”

DOs & DON’Ts
Succeeding as an in-house counsel

Learn the business. Understanding the business landscape is crucial.

Think strategically. Look at things from a distance for a broader perspective that adds value.

Hire a strong, capable team, and then delegate.

Be a team player. Recognize that no one can be an expert in everything. Work together with your legal teams and your business teams.

Be a roadblock. Counsel should find creative solutions to mitigate risk and enable achievement of business goals.

Think your role ends once you’ve looked at the “legal issues.” Modern counsel have to actively participate in business strategy and decision-making.

Get stuck in the details. It’s vital that you step away from the details and trust your team.

Be a perfectionist. You need to balance risk but allow the business to move.

Aeroplan built its in-house team in 2006, and not long after, it hired Greenberg full-time.

In the seven years since, the company and its parent, now rebranded as Aimia, have spun off from Air Canada and grown through mergers and acquisitions (of companies such as Nectar and Smart Button) to become leading global players in loyalty management. Now, helping to oversee Aimia’s more than 4,300 employees in 20 countries worldwide, Greenberg is part of an executive leadership team that helps her expand her understanding of the business through opportunities to participate in operational, strategic, and financial affairs. “I view myself as a business executive that happens to have legal training,” she says. “I love this job because I grow and evolve, and every year is different.”

Greenberg’s experience in marketing is helping her add value at Aimia. “Marketing in a small business teaches you to be creative, nimble, and results-oriented,” she says. “Law school teaches you logic and critical thinking. Now I’m combining all of these skills to influence the direction of our business.”

Her skills were especially put to the test during a critical period in 2013 when Aimia entered into intense negotiations with TD Bank Group (TD) and Canadian Imperial Bank of Commerce (CIBC). Her small team successfully negotiated deals to move half of Aimia’s credit card portfolio from CIBC to TD, developed commercial partnerships with both banks, and formed agreements with Air Canada to support the new partnerships. Greenberg says her nontraditional background helped her approach the deals holistically and provide added value that exceeded standard legal services.

As the dust from those deals settles, Aimia still has two institutions issuing Aeroplan credit cards, and Greenberg and her team are balancing the new deals, interpreting the provisions, looking for new partners, and analyzing their company’s marketing approach. Greenberg’s experience with both marketing and law have made her essential to her employer, and Aimia is growing and evolving thanks to her help.