‘Can AI sit there in a fleece vest?’: John Mulaney’s Salesforce roast was a masterclass in corporate comedy | Comedy

Last week, John Mulaney looked out on a crowd of corporate Salesforce employees and told them they were “imminently replaceable.

“You look like a group who looked at the self-checkout counters at CVS and thought, ‘This is the future,’” the comedian said. “If AI is truly smarter than us and tells us that [humans] should die, then I think we should die. So many of you feel imminently replaceable.”

Between its eccentric CEO, militant-sounding name, and the fact that most people struggle to understand what, exactly, the tech company actually does, Salesforce is something of an easy target. (It’s a cloud-based AI customer relations platform.) Whoever booked Mulaney to perform at Dreamforce, the company’s annual convention in San Francisco, probably didn’t think the former Saturday Night Live writer would say it to their faces though.

But roast employees is exactly what Mulaney did, in a set that made his audience “groan”, as the San Francisco Standard reported. Mulaney poked fun at corporate-speak – “the fact that there are 45,000 ‘trailblazers’ here couldn’t devalue the title any more” – and tech bro stereotypes: “Can AI sit there in a fleece vest? Can AI not go to events and spend all day at a bar?” He also referenced his son, who is almost three, saying: “We’re just two guys hitting wiffle balls badly and yelling ‘good job’ at each other. It’s sort of the same energy here at Dreamforce.”

The comedian’s appearance quickly made the rounds on social media, with users praising his brutal honesty. “We should bully tech nerds much more often,” one X user wrote. The software developer and tech commentator Dare Obasanjo tweeted: “John Mulaney at Dreamforce is how I feel every time I log into LinkedIn.”

Last year, the comedian Seth Meyers spoke at Dreamforce, similarly making fun of the company’s use of words like “trailblazers”, “roadmaps” and “architect.

“I saw ‘architect’ used as a verb. I don’t even think architects use ‘architect’ as a verb,” Meyers quipped. “If you were at a party and you said, ‘What do you do?’ and someone said, ‘I architect,’ you would think, ‘No you don’t!’”

Working comedians are often hired by companies to entertain employees at corporate events. These gigs tend to pay better than comedy clubs, where raunchy material is the norm – “ten to twenty times more”, said Jason Douglas, founder of Comedian Company, a booking agency for corporate events. (Salesforce is a client, along with Facebook, Google and General Motors.) “Real, significant tax bracket differences.” But working comedians have to play it safer with the jokes than their celebrity peers if they don’t want to alienate the revenue stream.

“A comedian who’s very rich can do what he wants,” said Douglas. “When you book a celebrity, you have to take what they’re going to give you. But a comedian who does corporate events all the time really knows how to read the room and what their parameters are.”

Douglas’s advice to performers, so as not to ruffle feathers: “I tell them, pretend you actually work for the company. Think about the jokes you’re doing. Would they get you fired if you work there?”

When Douglas speaks at Salesforce events, he usually starts with a tried-and-true joke that references a company quirk without going for the jugular. “The Salesforce building in San Francisco is the tallest building in the city, but it keeps sinking into the ground a few inches every year,” he said. “I always lead with something about that, and it gets a laugh, breaks the ice, like, ‘Oh, this guy knows about us.’”

Simon Mandel, a magician and comedian who has appeared at events thrown by Google, Harvard and Goldman Sachs, said that he always tries to communicate with bookers ahead of time to make sure he knows what “tone” they’re going for, and whether he should avoid certain awkward topics. “I performed at a holiday party once where the audience knew that half of them were going to be fired after the show,” he said. “Nobody told me.”

Mandel said his work tends to be “wholesome”, more PG. That plays better with bosses. “[When I perform], I constantly hear that the comedian last year upset half of the crowd,” he said.

Gianna Gaudini, a San Francisco-based event planner who used to run events for Google, AirTable and Amazon Web Services, said that it’s important to brief comedians on event specifications and to include rules in legal contracts. “Improvised jokes might touch on sensitive company or industry issues, so build clauses into your contract outlining any topics that are off-limits and could be offensive to certain groups,” she said.

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After 25 years of experience in corporate comedy, Greg Schwem believes audiences want to laugh at themselves – to a point. “I think they find it therapeutic,” he said. “A lot of times when comedians get onstage, they say things that the audience wishes they could say.”

Over a decade ago, Schwem performed for a McDonalds corporate gathering. The fast food chain had just spent millions of dollars in advertising rolling out a new breakfast sandwich that bombed. “[The bookers] told me that a couple of jokes about the sandwich was fine, but not to push it,” Schwem recalled. “They didn’t want me to do 10 minutes on it. I think it was their way of saying, ‘We prefer you talked about something else.’ I ended up not doing anything on the sandwich.”

Schwem doesn’t believe that Mulaney “crossed a line” with his set. Still, he said he’s learned that there’s a difference between “having fun with an audience and belittling them”.

“I have to remember that no matter how silly I think a company is privately, or how much I don’t understand what they do, this is people’s livelihoods and how they support their families,” Schwem said. “So it’s not my job to go onstage and say, ‘What the hell is this and why do you spend so much time on it?’ I want the audience to leave the event saying, ‘This is a really cool place to work because they hired that guy.’”

Mulaney commented on his Dreamforce set a few days later, during a set at San Francisco’s Golden Gate Theatre. “They gave me so much money,” Mulaney, who just welcomed his second child with actor Olivia Munn, said. “The whole time I was up there, I was thinking about all the money they were giving me, and it made me so happy.” He did not specify how much money.

While Douglas can’t speak for Salesforce, he said the higher-ups probably don’t care about some light roasting. (Representatives for Salesforce did not return a request for comment.)

“When any company hires a celebrity, they really just want those pictures after the show to post on Instagram,” he said. “They love the stand-up, but it’s really just about getting to meet a celebrity.”