At this week's 3% Conference, dedicated to supporting more female creative leadership in ad agencies, one keynote speaker brought an unusual perspective: he has been an agency creative as both a woman and now a man.

Chris Edwards described his transgender transition, while working at Boston agency Arnold 20 years ago while his father Ed Eskandarian was CEO. At the time, he applied all he had learned in the ad industry to re-brand himself and serve as an educator. He also had more than 20 surgical procedures, one every three months, for five years. He's currently seeking a publisher for the memoir he spent the last three years writing, called "Balls: It Takes Some to Get Some" (also the name of his keynote).

"Did my being a man help me be more successful in my career?" he asked. "Yes."

He attributed that partly to feeling more confident and happy after his transition; people even told him he looked taller.

"The creative department is a boys' club," he said. "It wasn't until I was in the club, inside looking out, that I realized how uncomfortable it could be for women."

He described one ghastly out-of-town business dinner after a pitch with seven men and a lone woman, at a restaurant the host said he chose for the Hooters-like waitresses; a visit to a strip club followed. From his new perspective inside the boys' club, Mr. Edwards said they didn't deliberately ostracize the sole woman and make her uncomfortable.

"It was unintentional," he said. "The takeaway is that for this dynamic to change, more women need to enter and stay in this industry. If there had been an equal ratio [of men to women], that conversation and strip club never would have happened."

He also shared a secret for getting plum assignments, raises and promotions: Ask. He said he never felt empowered to do that as a woman, but that if a guy wants a job or a promotion, he just asks for it. "You don't get everything, but at least I knew I wasn't holding myself back."

Mr. Edwards' polished, witty delivery of an emotional, painful story told with humor underlined his key takeaway for the enthralled audience: "Be a great presenter!"

"I managed more than 50 creative teams, and women consistently let men take the lead when it came to presenting their work," he said. "It's not just about creating the work, it's about selling the work."

In another session, SapientNitro announced the launch of Returnships, a program to offer women returning to the workforce a fast track back into agencies, and its website invisible.careers. The idea is to identify skills agencies are looking for and provide re-training in those skills followed by an agency internship of one to three months.

"We think this will be the secret sauce to help people get back in the market," said Helene Cote, program director for the 3% Returnships program. Ms. Cote appealed to audience members to consider being a candidate, a host agency or funding a sponsorship.

At a CMO Roundtable moderated by Lisa Cochrane, Allstate Corporation's former senior VP-marketing, Gail Tifford, Unilever's VP-media and digital engagement for North America, appealed to creatives in the audience to help her come up with a better name for the Unilever group she co-chairs, Womens' Interactive Network (WIN).

Allie Kline, CMO of AOL, described what she's looking for from creatives: "The consumer has taken control at a rate that's never happened before ... One of the most valuable things a creative can do is show brands how they can get ahead of consumers."

"This is a journey," said Suzy Deering, CMO of eBay North America. "The best way to make a difference is to show you can lift up women in your organization."

In another session, with recruiters as panelists, the women acknowledged that it takes more than just selecting a diverse pool of applicants—sometimes unconscious bias and actions can undermine the hiring process. Jenny Tieman, associate director, creative recruitment at R/GA, said she has seen cases where creatives, without even realizing it, tend to favor candidates who have a background similar to theirs.

The annual 3% Conference, started by 3% founder Kat Gordon and held for the first time in New York, drew about 800 attendees.

Contributing: Natasha Madov