Handling the affairs of Ashley Madison

Handling the affairs of Ashley Madison
Photo: John Hryniuk
Life is short. Have an affair. That’s the slogan of highly successful — and highly controversial — online dating site Ashley Madison. The site, owned by Avid Life Media, is designed for “discreet encounters” for people seeking an affair.

Avid Life Media also owns a few other properties, including Established Men (a dating service that connects “young, ambitious women with successful, established men”); Cougar Life (a dating site for women who want to share their real age and personal situation); and The Big and The Beautiful (a dating site for women “with curves who don’t like to play games”).

For Avi Weisman, vice president and general counsel for Avid Life Media, it’s not exactly a typical job. But Weisman never really wanted a typical job.

“I knew I didn’t want to have the normal or typical career path,” he says. “By that I mean working on Bay Street, working up to partnership level, that path. I moved in-house fairly quickly.”

Weisman, who has an MBA from York University’s Schulich School of Business, is a one-man legal department at the company’s headquarters in Toronto. He’s responsible for everything from business development and strategy to legal issues related to international launches and digital marketing, as well as managing external lawyers across 46 countries where the company operates.

It’s a big job, considering how fast the company is growing. Last year Ashley Madison launched in 20 new countries and now has 32 million members.

“While we all understand that the service this company offers is somewhat controversial, the reality is — whether fortunately or unfortunately — infidelity is universal and it was prevalent long before Ashley Madison was around,” says Weisman. “And that’s what allows us to expand internationally relatively seamlessly. There’s a universal demand for our services.”

Because of this rapid expansion, his role includes a large international component. “We’ve always been successful in North America and one of our goals in 2014 was to continue to launch successfully in international and emerging markets,” he says.

That’s challenging, though, because while there may be universal demand for the company’s services, every market is uniquely different. Consider the cultural differences between India, Israel, Turkey, and Eastern Europe.

“All these countries have different frameworks, different societal norms, and that was a big challenge,” says Weisman. A lot of research is done before launching into a new country, he added, from average income to regulatory requirements and societal norms.

“We evaluate the different international opportunities from a lot of different perspectives — demographics, GDP, but also the legal and regulatory framework. So I’ll provide a first-level assessment and then if we need to engage external counsel we’ll do that as well.”

These new markets can be challenging, considering the nature of the site. Last November, Philippine Justice Secretary Leila de Lima sought to block the site from the country, charging that it facilitates crime. Adultery is against the law in the Philippines, punishable with jail time, even though the law is largely not enforced (and many powerful men flaunt mistresses).

Singapore and South Korea have both banned the site, citing that it threatens family values. Singapore’s Media Development Authority said in 2013 that the web site was a “flagrant disregard of our family values and public mortality,” and would work with Internet service providers to block the site.

“Some countries are more conservative than others, some countries add different challenges from a political standpoint as well,” says Weisman. “There are countries that, once we do our research, may require a longer road map to launch.”

Despite these challenges, the company has experienced year-over-year double-digit growth over the past decade, according to Weisman. A big part of his role is to help develop strategies to continue that growth.

“It’s funny, people always assume my job is heavily focused on litigation. It’s actually not, thankfully. We use external counsel for any litigation matter,” he says. “We have no litigation right now — my litigation mandate is nil. There have been times when it’s part of the role to manage the litigation.”

But what about those angry spouses? “A lot of that stuff is dealt with at a customer service level,” he says, however there has been the odd case: Back in 2012, a North Carolina man sued Ashley Madison when his then-wife used the site to hook up with another man (he also sued the other man). Robert Schindler sought more than $10,000 in damages, claiming alienation of affection and criminal conversation. (North Carolina is one of a handful of states that still awards punitive damages when a marriage fails and someone else is to blame.)

“Most people . . . think there must be a lot of litigation, I must have some crazy stories,” says Weisman. “I’m a business lawyer. The vast majority of my time is spent on business and commercial and strategic issues, not on the salacious [stuff].”

All marketing, for example, has to be vetted by Weisman — whether it’s a banner ad, billboard, radio spot, or TV commercial. “There are times we have to reel something back if it would be a violation of some law,” he says. “I personally deal with advertising regulators in different countries — I have to work with them to get our TV spots approved, and sometimes our spots can only air at certain hours of the night.”

The same commercial that runs in Canada could run in Australia or Israel but there may be some tweaking required. “We always are open to working co-operatively and even collaboratively with the different regulators and advertising approval boards to make sure our ads get green lit,” he says.

It doesn’t always work out though: In 2009, the Toronto Transit Commission turned down a deal to wrap a streetcar in the company’s motto. And in 2001, CTV turned down the company’s Super Bowl ad (where a woman announces to a boardroom that her husband is having an affair to a round of approval).

It’s a job that keeps Weisman on his toes. “I can honestly say the day-to-day here is exciting, much more so than in past roles, much more unpredictable,” he says. “We get to see and appreciate our successes here.”

Weisman spent almost seven years as senior legal counsel at Allstream, followed by a few years at Avaya — both multibillion-dollar communications and networking technology companies many Canadians have never heard of. That’s not really an issue that Weisman has in his new role. Most people have heard of Ashley Madison — whether they love it or hate it.

“Right now it’s one of Canada’s most successful technology startups,” he says. “At the end of the day, when the opportunity presented itself, it really was a no-brainer. I came from legacy institutionalized companies that are constantly in cost-cutting mode [and went] to a company in constant growth mode.”

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