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the future of work

It has been three years since Facebook chief operating officer Sheryl Sandberg wrote Lean In and six years since she gave the TED talk that ignited the idea behind the book – that women should give it their all to get ahead. Yet, it still isn't any easier for women to "lean in" after taking a break from their career.

Take, for example, 43-year-old Ya'ara Saks. Ms. Saks worked in Israel for almost 15 years, in roles that included senior foreign relations adviser to a government minister. She moved back to Toronto 10 years ago, not long after having a baby. Two years later, she became pregnant with her second child and decided that juggling full-time work and motherhood was too difficult. So she moved to project-based work.

Six years ago, when Ms. Saks sought to return to full-time employment in fundraising, the non-profit sector or politics, she found the reception to be less than welcoming.

"Everyone just looks at you and says 'What did you do for all those years?'" lamented Ms. Saks, now divorced, who makes her living running a project management consulting business and teaches yoga to keep her in a "happy place."

She recounted that in multiple job interviews, the hiring manager would reiterate that the role was full-time and question – either directly or indirectly – her ability to manage the job as a single parent.

"I'm fairly familiar with the concept of time not being my own. I have a master's [degree] in international relations and economics. There is no reason why I'm not qualified to do what I do, but all employers see is that I'm a single mom and how are they going to make this work?" said Ms. Saks, whose children are now 8 and 12.

According to a 2014 Pew Research Centre study, about one in 10 mothers with a master's degree or more choose to stay home in order to care for their families. It's a trend that Lisa Belkin captured in The New York Times more than a decade ago in the groundbreaking piece called The Opt-Out Revolution. One financial crisis later, many of these affluent, educated women want back in but find the doors remain anything but open.

There are those working hard to change the status quo, such as Jennifer Gefsky, who co-founded a new company called Après, which Fast Company dubbed "The LinkedIn for Women Who Have Taken a Career Break." Après, which claims to have 10,000 users, matches women re-entering the work force with companies hungry for diversity. Ms. Gefsky and her co-founder Niccole Kroll launched the company since they, like Ms. Saks, were surprised by how challenging re-entering the work force was for experienced professionals.

Ms. Gefsky said she surprised herself when she left her role as vice-president and general counsel for Major League Baseball.

"I became the cliché of not doing anything well and reached my breaking point. … I never thought I would stop working in the corporate world and then life happened," Ms. Gefsky said in an interview. Meanwhile, her co-founder opted out after being diagnosed with lymphoma. This experience seemed out of sync with the needs of Corporate America, which Ms. Gefsky believes is now hungry to hire these returnees since many companies lack gender diversity at the mid-senior levels.

"Our mission is to literally go company by company and educate Corporate America on why this demographic matters and why they are important to your work force. You not only get great employees, you are sending a message to your customers and clients. The companies we are speaking to understand this," Ms. Gefsky said.

Ms. Gefsky said Après already has Canadian members and one employer, the Toronto Blue Jays, signed up for their service.

Still, she sees challenges ahead.

"The mindset that is most difficult to change is the one where companies look at this demographic and think 'Are they really committed?' 'Do they really want to come back and are they able to come back?' What we are finding is that these women have to come back. It's not that they are bored and looking for something to do in the afternoon. They have to come back for financial reasons. They are financially motivated," Ms. Gefsky said.

Reva Seth, author of The Mom Shift, agreed that battling the stereotype of the uncommitted mother remains a top priority in helping to pave the way for women to return. "Since I published The Mom Shift, the reality is that in the boardrooms and hallways of Canada's organizations and companies, the progress on women being able to enter the work force easily after an extended break really hasn't changed much at all," Ms. Seth acknowledged.

However, she remains optimistic that change will happen once men, specifically senior-level baby boomers, continue to seek better work-life balance. "Ironically, these guys are most likely to be the change agents that will benefit returning working moms," she said.

Leah Eichler is founder and CEO of r/ally, a machine-learning, human capital search engine for enterprises.