As VP of media for Walmart U.S., Jill Toscano has helped move the country’s biggest retailer into new territory in a big way.

Toscano's team has run more than 100 shoppable livestreams across nine platforms. Among things she’s learned in the process, Toscano said, are how to turn livestreams around quickly; “embrace imperfection” rather than try to make everything perfect; and realize that events drawing devoted fans—such as one with “Pioneer Woman” Ree Drumond—are better than just drawing big numbers.

Through a growing partnership with Meredith, Toscano’s team also has taken meal planning to a new level with recipes that let people fill online shopping carts. “Our aspiration is to shorten the distance between inspiration and purchase,” said Toscano, and the Meredith partnership does just that.

Toscano also has led the effort to step up investment in minority-targeted and minority-owned media, helping launch a Cultural Engagement department. In just a year, the team added more than 10 new multicultural media relationships, including with TikTok’s first Black creator house, and launched Black-curated gift guides on the platform after noticing a lack of diversity in existing holiday content.

What advice would you give your younger self?

I would tell my younger self to not feel like an impostor just because you're in a new industry or a new company or because you're not sure how to handle a sticky situation. I would tell myself to turn those feelings of doubt into a curiosity to learn more and a desire to hear from others and really embrace the humility to own up to not knowing all the answers.

What’s the biggest risk you've ever taken?

Taking a bit of a career break. I had grown up during a time when the power suit was just becoming iconic. My favorite movie was “Working Girl,” and I had made a wage since I was 14 years old. But it was something that I had wanted to do for a number of reasons, and while it was scary at times, I look back now and I have not once regretted that decision because I think that helped bring me where I need to be today.

If you weren't doing your current job, what would you be doing and why?

I have always loved art. So I often like to imagine that if I had not pursued a career and worried about a 401(k) I'd be one of those artists in Central Park or by the subway street entrances with an easel and charcoal and paints and capturing everyday people as they go about their daily business.

What should the industry be doing to encourage more women and people of color into its ranks?

It's important that we have internships and fellowships that bring young, diverse talent into our industry right from school. But I'd also advocate for more leadership shadowing mentorship programs at more middle to senior levels of management because I think we really start to see the drop-off then of women and people of color in C-suite positions.

What is the biggest lesson you've taken away from the pandemic?

We all have tremendous potential for ingenuity from the way that we work with one another to the stories that we tell one another. Nobody planned for the pandemic. We couldn't have planned for the pandemic, and so we were literally making it up as we went.