She won a New York Press Club award for her story on the Nikki Catsouras photographs controversy about a family's struggle to remove their daughter's gruesome death photos from the internet.

[10] Bennett left Newsweek after it merged with The Daily Beast to become the executive editor of Tumblr[11] and later worked briefly as an editor at Sheryl Sandberg's nonprofit foundation, Lean In,[12] where she created the "Lean In Collection with Getty Images", a photo initiative to change the depiction of women and LGBTQ families in stock photography.

Bennett headlined The Times's women's conference, The New Rules Summit,[19] in 2019, and guided the newspaper's coverage of the centennial of the 19th amendment.

[20] Bennett has written extensively on the #MeToo movement,[21] including investigating allegations of sexual misconduct against the playwright Israel Horovitz,[22] and reporting from the civil rape and defamation trial brought by E. Jean Carroll against Donald Trump.

Among them: An attempt by Playboy to "rebrand" for millennials[24] (and a similar effort by the Miss America pageant[25]); a class at Smith college, led by the scholar Loretta Ross, to teach students to "call in" instead of calling each other out;[26] columns on TikTok trauma; going to see the Barbie movie with the feminist scholar Susan Faludi,[27] and her quest to find "fun" in a time of darkness [28] Bennett has profiled celebrities and public figures including Pamela Anderson,[29] Amanda Knox,[30] Monica Lewinsky,[31][32] E. Jean Carroll,[33] Jennifer Aniston[34] and Katie Hill.

In the episode, Alex (Jennifer Aniston) lands the interview with the fictional Jess Bennett, who was the first person to predict the overturn of Roe v. Wade on her website.