Meet the top lawyer at one of Toronto’s most buzz-worthy companies

As Wattpad’s general counsel, Jamie Greenberg is using his legal skills to help disrupt the entertainment industry
Illustrated portrait of Jamie Greenberg
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The late 2000s were a thrilling time to work in the Canadian telecom industry. BlackBerry was the country’s hottest company, the smartphone had revolutionized mobile technology and bold upstarts — Mobilicity, Wind, Public Mobile — had declared war on Goliaths like Bell, Rogers and Telus. Jamie Greenberg had a front-row view of the action. In 2009, he launched his legal career at the CRTC, where he worked as an articling student and, briefly, as legal counsel. During his tenure at the commission, he was part of the regulatory team that oversaw the merger of Shaw and Canwest and the entry of several new telecommunications firms. “The more I learned about these companies,” he recalls, “the more I thought they would be a really interesting place to land.” 

At the end of 2010, Greenberg joined Public Mobile. He worked in a bevy of practice areas — corporate, regulatory, privacy, IP and more — until the company was acquired by Telus in 2014. He could have stayed on at Telus, but the thought of climbing the corporate ladder didn’t excite him. “I didn’t see myself working in a 40,000-person company,” he says. 

Instead, he wanted a fast-paced, hands-on challenge. So he left the world of law to co-found Facet4 Media, an entertainment production and distribution company, with his father and aunt, both long-time TV executives. In addition to serving as general counsel, Greenberg scouted for television shows, developed scripts, pitched networks and coordinated production. He had no idea at the time, but that experience — seemingly peripheral to the legal profession — would help him land the best job of his career. 

Photo of Jamie Greenberg standing outdoors next to a wooden fence

Jamie Greenberg

General counsel, Wattpad 
Year of call: 2010

In late 2018, Greenberg learned that Wattpad was looking to hire a lawyer. The buzzy Toronto-based company had started in 2006 as a platform for writers — from amateurs to Atwood — to share fictional stories directly with audiences. The business made money by running ads. As it grew, the company worked with writers to adapt the most successful stories into books, movies and TV shows, giving the writers a way to monetize their creations. To date, more than 1,500 Wattpad stories have found a home on bookshelves, in film and on television, including the popular After movie franchise. 

Wattpad wanted to hire a lawyer with in-house experience who also knew the ins and outs of media, tech and entertainment law. Greenberg ticked every box. “Jamie came in with such unique experience,” says Jeanne Lam, the president of Wattpad. “He was an obvious unicorn.” 

As the company’s general counsel, Greenberg has a wide-ranging job description. He helps formulate the terms and conditions for Wattpad’s 90 million users. He helps ensure that the company abides by the privacy requirements of more than 150 countries. He also handles internal employment law, contributors’ contracts and NDAs, and the legal details of Wattpad’s partnerships with Hollywood studios like Sony Entertainment and publishing giants like Penguin Random House. 

Tapping into his TV background, he even signed on as executive producer for the film Float, a teen romance based on a hit Wattpad story. “It’s an incredible feeling,” says the 37-year-old, “when something is on your desk one day and on the cover of Variety the next.” 

His most demanding task to date was stick-handling Wattpad’s approximately US$600-million sale to Naver — a tech behemoth sometimes called the Google of South Korea — which started in December 2020 and closed in May 2021. Greenberg led dozens of mostly external lawyers, ensuring that Wattpad’s investors and bankers were satisfied with every aspect of the acquisition. “Was it hard? Yeah,” he says. “But it was the most fun I’ve had in my career.” 

That sunny attitude continues to impress Lam. “Often, legal counsel is called in when things are not going well,” she says. “But you can always look forward to a conversation with Jamie.” Lam says that Greenberg understands not just the law, but how to manage people, relationships and the company’s strategic goals. “I would work with Jamie for the rest of my career if I could.” 

Once the sale to Naver was complete, Greenberg caught up on lost time with his family — he has two young children with his wife, Angela Greenberg, the manager of professional development at the Advocates’ Society — and shifted his focus to Wattpad’s expanding Paid Stories program, which compensates the platform’s most popular writers for their work. So far, the program has paid out more than $1 million to hundreds of writers, but it also raises tons of legal questions: What rights do authors retain? What are Wattpad’s obligations? “There’s no legal textbook that tells you how to do these things,” says Greenberg. “We’re doing stuff that hasn’t been done before in traditional publishing and entertainment.” 

Timeline of a general counsel

2003: Greenberg begins a joint undergraduate honours degree in political science and religious studies at McGill University. 

2006: He starts law school at Osgoode Hall. 

July 2009: Greenberg articles at the CRTC. “The commission was always in the news,” he says, “so I was working on files that were making headlines at the time.” 

June 2010: After getting called to the bar, he joins the CRTC as legal counsel. 

September 2010: He moves to Public Mobile as a manager of legal and regulatory affairs. 

2015: After Telus buys Public Mobile, Greenberg co-founds Facet4 Media. The company’s most notable production, a Canadian-Irish thriller series called Acceptable Risk, premieres two years later on Super Channel and Acorn TV. 

2019: Greenberg joins Wattpad as general counsel. His first two years at the company involve a pandemic, a US$600-million-or-so sale and the birth of his second child. “Hopefully, my next year will be a lot more vanilla.” 

This is a story from our Winter 2021 Issue.

Illustration by Kelsey Heinrichs. Photo by Nechama Laitman.