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Dan Rosensweig

Chief Executive Officer

Santa Clara, CA

I hope more women find the courage to follow their passions and trust their instincts.

I had just taken on the role as CEO of Chegg. Going into it, I knew my assistant Heather (who was pregnant with her second child) would soon be taking maternity leave for three months at the same time I was starting my new job. What I didn’t know was that, before she even returned from that leave, she would decide to take her career down another path.

During her time away, she decided she no longer wanted to be my assistant, but was unsure of how to approach me to discuss a possible role change. She also struggled with concerns over her job security and benefits, as her husband was recovering from a serious illness and had also recently been laid off after 11 years with his company. She was torn between trusting the stability of a known role and asking for what she wanted and felt she deserved.

Internal doubts took hold. Should she share her aspirations with me, at a time where she was potentially vulnerable financially and professionally? Would I encourage her to leave the role she had for years with me, (which was not in my best interest), to pursue her own goals?

Despite the uncertainty of how I might respond, Heather chose to take the risk and lean in. While on maternity, she asked for a meeting and expressed her interest in a new role. She said she would come back in whatever position was in the best interest of Chegg, but rather than asking me to decide which role was best, she presented why it was in my, Chegg’s, and her best interest to take on something new. I encouraged her to make that transition, follow her passion, and find a place that was both good for Chegg that also met her needs.

Ultimately, Heather was promoted to run Chegg for Good, the philanthropic arm of our brand. She has taken on major projects that have improved our business and has grown successfully in to a role very different from the career path she had been on.

I'm glad she was able to discuss this with me and lean in to this difficult decision. I hope more women find the courage to follow their passions and trust their instincts. The end result of this situation was both good for the company and for Heather – which will hopefully encourage her to lean in again, and again throughout her career.