Debra Tenenbaum, Yapstone

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When it comes to finding the right talent for a position, Debra Tenenbaum knows a few things about how to set someone up for success — even when the needs of the business change.

Yapstone has grown over the years from being a startup focused on digitizing the monthly paper rent check to an international company that processes over $20 billion in transactions for vacation and rental properties, powering marketplaces and much more. A key element of its success has been Yapstone’s ability to attract, grow and retain talent for its U.S. and overseas operations.

Leading the charge in building and developing the Yapstone workforce is its executive vice president and chief people officer, Debra Tenenbaum, who is one of PaymentsSource's Most Influential Women in Payments for 2019. She joined the company in 2015, just in time to lead its recruiting efforts for a new international headquarters office, which opened in Drogheda, Ireland in 2016 (the company had first established its Irish operations in 2012).

Along with the new Irish facility came the commitment to hire more than 200 highly skilled engineering and technology workers, according to the Irish Times. The challenge for filling seats requires a long-term view of potential candidates. Tenenbaum told the Irish publication, Silicon Republic, that recruiting is not something that can be done only periodically when you have positions to fill. “We don’t just look as recruitment as a point in time for tech talent; it’s about building relationships, staying connected and then, when the time is right, bringing them back in.”

To draw inspiration for success in her career, Tenenbaum is motivated by travel. “I have always been passionate about travel and taking my kids with me to expose them to other cultures," she said. "Travel teaches you to be more inclusive to differences in people and cultures. It fosters a willingness to be more open-minded to a variety of things.”

Ever since Tenenbaum was in college, she’s had the travel bug. She’s been to every continent with the exception of Antarctica. However, she came close to going when she visited her son in Argentina a while back.

In terms of offering advice to women entering financial services and technology industries, her view is refreshingly clear: “Have an authentic leadership style. Be true to your principles and try not to morph into what people expect you to be.”

Tenenbaum notes that women are an important asset to any business because they approach problem-solving differently than men, but can be dissuaded from joining a specific company due to its recruiting efforts. “Companies need to be more inclusive in order to get a fully rounded workforce. It’s important for an organization to review its recruiting practices to make sure there are no inherent biases that will discourage or impede certain groups from joining a company ,” Tenenbaum said.


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