These Marketers Reveal How They’ve Aimed High and Supercharged Their Careers

After a riveting four days of online learning and chatroom schmoozing, Brandweek attendees tuned into “Dream Big” on Friday, a midday workshop moderated by the former head of Uber, Taj Alavi, and Rachel Webber, CMO and president, corporate strategy, of Playboy. The two marketing mavens shared how vision boards, victories against impostor syndrome and self-acceptance have allowed them to steer their careers in the direction of their dreams.

Alavi is one of the 230-plus marketing leaders serving as mentors in Adweek’s Executive Mentorship Program and a current adviser on the board of Plenty, an indoor vertical farming startup based in San Francisco. As of last month, she was the senior director of global brand marketing at Uber, before stepping down from her role. Prior to working at Uber, Alavi was the head of global brand marketing at Instagram from 2015 to 2018. She shared during the workshop that she still considers her position at Instagram a lottery win, recognizing it as the opportunity that helped her grow and took her career to the next level.

Alavi also noted how she is passionate about vision boards, and finds them to be valuable visual and kinetic tools for mapping out careers and for pinning down higher-level personal and professional goals.

Webber, who spoke with Adweek’s executive editor Stephanie Paterik last year on Top of Mind about the direction Playboy’s marketing was taking (while paying homage to the publication’s 65-year history), mentioned how her own vision board was filled with tangible, achievable things to get done within the year that were tied to those higher-level goals, such as financial freedom. “I think it’s really important to embrace just putting one foot in front of the other sometimes,” Webber said, “and creating that ongoing motivation, resilience, perseverance, and turning that all into muscle memory is so crucial to creating your own personal strategies for dreaming big.”

Alavi and Webber both disclosed how, instead of being in competition with themselves or with society’s expectations on success, they were kind to themselves and in tune with the criteria defined by their life stage. Instead, they adhered to their goals while also remaining open-minded and flexible enough to dive into unprecedented challenges and new experiences.