This is the first installment of Digiday’s daily Advertising Week Briefing, our essential guide to key highlights, what we’re overhearing, previews of the day ahead and more. Sign up to receive it every day this week at 6 a.m. Eastern time at digiday.com/awemail.

Have you been to Times Square recently? Skip the Uber and take the subway. It’s going to be a long day. Here’s a look at the day ahead.

Credibility crisis will be the hot topic

It’s in fashion to be disappointed about the state of digital media today. Procter & Gamble’s chief brand officer Marc Pritchard kicked off the practice early in the year, followed by a sort of domino effect of brand marketers publicly speaking about how digital media has failed them. You have Restoration Hardware’s CEO Gary Friedman telling a striking story about how the company’s online marketing strategy was predicated on 22 words — and how the large majority of online ad spending has been wasted. And there are marketers who have taken real action, with companies like P&G and Chase slashing spending and where their ads are appearing and finding that, surprise, their performance wasn’t affected.

Railing against how much of digital advertising is in a black box is in fashion, and it should be the big issue at Advertising Week this week as many major marketers gather in one place.

This is happening even as CMOs take on in some ways the role of a politician. Expect stump speeches from some of them as they do the hard job of convincing their constituents — from individual brand managers to partners to, yes, shareholders — that they care about the issue in an effort to get everyone on their side.

— Shareen Pathak

Mr. Cannabis

Marijuana may sell itself, but cannabis brands still need some ad help. As a result, the sector, which is estimated to be worth $50 billion by 2026, needs some help from weed agencies — this year’s big new topic at Advertising Week.

Drake Sutton-Shearer, co-founder of Prøhbtd Media, a production house in the marijuana industry, will make his Advertising Week debut today at the conference’s first series of talks on cannabis marketing. Sutton-Shearer said Advertising Week reached out to his agency last year, asking if they’d be interested in getting involved, as cannabis marketing was topical.

“Cannabis marketing is a growing area, and marijuana legalization definitely helps the growth,” said Sutton-Shearer. “The stoner stereotype has been existing for a long time. So at this year’s Advertising Week, we really want to destigmatize cannabis marketing.”

Branding and marketing for weed brands is not just as simple as creating an ad campaign and a marketing schedule due to strict advertising regulations in the industry, said Sutton-Shearer. For instance, brands in the cannabis space are not allowed to target or retarget children, meaning that they usually don’t use social networks like Facebook or YouTube to advertise their products, he said.

“Without Facebook or YouTube, it immediately reduces the opportunities for [weed companies] to reach their audience,” he said. “We usually produce original shows that contain brand integrations and then distribute them through Apple TV and Roku.”

— Yuyu Chen

What’s in and what’s out

We’ve brought together a decade of experience covering Advertising Week to bring you the definitive guide to what’s in and what’s out. Check out the full version here.

Coming up

10 a.m. The Advertising Week Tech Xperience walks you through the future at 4 Times Square all day, so you can play with artificial intelligence, virtual reality, robotics and 3-D printing.

12:15 p.m. Keith Weed, Unilever chief marketing and communications officer, takes the stage to talk about the digital strategy of one of the world’s biggest advertisers.

1:30 p.m. JWT unveils the results of a new study on gender representation with the agency’s CEO, Lynn Power, and speakers from the Geena Davis Institute on Gender in Media.

2:15 p.m. WPP chief Martin Sorrell joins writer Ken Auletta for a fiery conversation.

5 p.m. Quantcast cocktails, Skylark

6:30 p.m. Opening Gala, Radio City Music Hall

7:30 p.m. Opening Gig with Nas at Irving Plaza