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Career Path: How Sun Life’s Melissa Kennedy is an agent of change

"I like change and I enjoy taking risks," says Kennedy. Her career to date is proof

Career Path: How Sun Life’s Melissa Kennedy is an agent of change


1987 – establishes intellectual discipline 

“I always wanted to be a lawyer; I was argumentative by nature. I loved words: My favourite subject in third grade was grammar. 

“I had no idea what law school to go to — I fell into the University of Toronto because I wanted to live in the city — but that experience was seminal. It was a collaborative, supportive environment and emphasized rigour and honesty. The intellectual discipline of being a lawyer was established for me at U of T.” 

 
1993 – joins a startup 

After four years as an associate, Kennedy moves to Kelly Affleck Greene, a startup litigation boutique firm founded by several partners from her old firm. 

“It was a big decision for me — I agonized about that, but I like change and I enjoy taking risks. I had a vision of what the firm could be and wanted to be there on the ground floor. It seemed like a unique opportunity to be more hands on and have control over my destiny.” 

 
2001 – joins OSC 

Bored with the practice of law, Kennedy is looking for a new opportunity when she sees an ad for a position at the Ontario Securities Commission. 

“I went in for a chat, and it turned into an interview and I was hired. They didn’t even do a search. I have a fascination for the capital markets: We did high-profile investigations — we were at the forefront of everything. My biggest case had so many documents we stored them in an aircraft hangar.” 

 
2003 – joins CIBC 

Approached by CIBC, Kennedy’s long-standing fascination with business lures her to join as head of litigation, and, suddenly, she spearheads every lawsuit, investigation or regulatory matter.  

“I joined two weeks after the Enron investigation was announced. I was there for everything: If I missed my tennis lesson, people would ask what was up at the bank and, sure enough, two weeks later would come an announcement. I learned to work with people to fix things in a highly collaborative way.” 

 
2009 – becomes general counsel 

After being approached to meet to discuss the general counsel’s job at OTPP and “hitting it off” with the CEO, Kennedy is offered the position, just days before a life-changing tragedy. 

“I got the offer on Thursday, celebrated on Friday and then my husband died on Sunday. He dropped dead during our tennis lesson. I realized I was totally in charge of this family and had to progress. General counsel is big deal, a huge job. It was a leap. 


2014 – joins Sun Life 

“Pursued hard” by Sun Life, Kennedy finally agrees to a meeting when the head of HR “asked me to do Dean Connor the honour of having a coffee with him. I was at a juncture with OTPP — we had just finished a big negotiation and felt good about it. Sun Life is a unique company, a global Canadian company, headquartered in Toronto. I did my due diligence and told myself: ‘OK, Kennedy, this is your last move; better make it a good one.’” 

 
2019 – champions sustainability 

Now accountable for legal, compliance, government relations and regulatory affairs, Kennedy has also taken on the post of Sun Life’s executive sponsor of sustainability. 

“Sun Life was involved in sustainability long before I joined. However, since I was made executive sponsor, we’ve really ramped it up. Now, sustainability support is included in all our scorecards. I want it to be a business initiative as well as the right thing to do. It’s a major differentiator for us.” 

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