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Lessons to Succeed: Rupal Hollenbeck’s Playbook

Qiyang XuHi! My name is Xu Qiyang; I’m a fresh graduate who recently joined Oracle. To start off my journey here on the right foot, I attended the Oracle Women’s Leadership (OWL) community’s first #HerStory session in Singapore, where Senior Vice President of Corporate Marketing, Rupal Hollenbeck, shared insights on leading with passion, creating change, and building future generations.

It was fascinating to hear Rupal recall her experiences, impressing the audience with her authenticity, ambition, and eagerness to learn. Here are a few of the key insights I took away from her discussion, as well as some pictures from the event.

Her Story - Rupal Hollenbeck

What truly matters

As she was starting out in her career, Rupal learnt a hard lesson: working long hours isn’t enough; creating impact is what truly matters. To Rupal’s shock back then, her previous employer laid off some of her most productive colleagues during a major restructuring of the company. “Impact matters, not output. Value matters, not volume. It’s about producing work of the highest quality,” she said. That statement provoked me to wonder: What can I do to create impact for Oracle? What sort of impact do I want to generate?

Listening is fundamental

Rupal went on to explain how her career accelerated, as she became her previous employer’s Director of Sales and Marketing. To be a better leader and make well-informed decisions, Rupal resolved to treasure diverse perspectives and surround herself with differing opinions. “It’s important to just deeply listen, to listen with empathy—not listening to react, but to understand,” she recommended. Rupal’s listening skills are probably one of the qualities that have brought her to the top of her game, where she’s now working to transform the face of Oracle.

Juggling work and life

Many of the questions from the rapt audience were about work-life balance. For Rupal, there are seasons when work is a priority, and when she relaxes or spends time with her family. The mother of two loves throwing herself completely into work—her resulting happiness is infectious to her family. “When you’re truly enjoying your work, you go home as a better woman, wife, and mother,” Rupal shared. She reflected that “there’s a lot you can learn from being both a mother and a leader,” and further encouraged other working mothers to share their advice.

Her Story - Rupal Hollenbeck

A leader to rally around

It was inspiring to see so many leaders such as Alison Sibree, Cherian Varghese, Sujith Abraham, Sotis Dramalis, and Rachna Sampayo, who all firmly focus on supporting an equitable future for Oracle women, amongst the audience. As a leader, Rupal wants to create an environment ripe with opportunities for future leaders. “I’ve made my career by taking on meaty challenges,” she stated. “I saw an amazing opportunity in Oracle to build the next generation of leaders—the greatest impact I can make on any team is to leave it better than when I started.”

Her Story - Rupal Hollenbeck

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