Company Retreat Bosses on Finale Reveal, Casting Sia, Anthony and More

SPOILER ALERT: This article contains spoilers for the ending of “Jury Duty Presents: Company Retreat,” now streaming on Prime Video.

The “Jury Duty” executive producers have done it again.

Co-creator Jake Szymanski and director Lee Eisenberg pulled off another hilarious season of TV and fooled an oblivious main character, this time a temp assistant named Anthony Norman, into believing the absurd workplace shenanigans happening around him were real. But this time, “Company Retreat” went even bigger than their 2023 breakout hit “Jury Duty.”

The “Company Retreat” finale, now streaming on Prime Video, reveals how they pulled off the season. After interviewing 10,000 applicants for a fake temp job, Szymanski and Eisenberg chose Norman to anchor the show, about hot sauce company employees on a corporate getaway. “Company Retreat” grew from a single courthouse set on “Jury Duty” into a multi-acre camping lodge. The second season had 48 cameras (up from the 29 on “Jury Duty”) and 3,600 hours of footage (versus 2,100 hours). Every character who worked at Rockin’ Grandmas Hot Sauce also needed to memorize years of backstory, in case Norman asked someone a question about their job.

Szymanski and Eisenberg also upped the drama on “Company Retreat.” Rockin’ Grandmas CEO Doug Womack (Jerry Hauck) was originally going to pass the business down to his slacker son Dougie Womack Jr. (Alex Bonifer), but then enters into a deal with Triukas Group, an unfriendly conglomerate. Despite working at Rockin’ Grandmas for only two weeks, Norman grows close to his fictional co-workers and fights to keep them independent from Triukas. In the shockingly emotional finale, Norman bursts into the meeting room just in time to stop Womack from signing the deal.

After the deal is called off and Rockin’ Grandmas is saved, the cast reveals the truth to Norman and he’s awarded $150,000. Speaking with Variety, Szymanski and Eisenberg discuss how the season nearly fell apart, how they landed Sia for the talent show and which actor nearly ruined the show by saying their wrong name.

What stood out to you from Anthony’s application that made him the right hero character?

Jake Szymanski: Anthony’s so great, and he’s a multi-faceted person. He’s very kind and thoughtful. He’s also confident in knowing who he is, which is important because we’re looking for someone who’s never the butt of the joke. We’re never punching down and trying to make fun of our hero, but we do want him surrounded with interesting characters who are making questionable choices a lot. You need someone who is confident enough to say, “No, I can step up and help, or I can offer you my opinion” and also be judgment-free enough to not make anyone feel bad that they’re acting a little strange or crazy. He’s not going to come down too hard on the characters. He’s a real go-getter. He’s kind, and has a great work ethic.

Lee Eisenberg: I think he’s just inherently decent. The show has a hopefulness and optimism and a lack of cynicism. The world that we’re living in right now has all of those things in spades. There’s something slightly refreshing to see someone like Anthony who makes the right decision, who wants to support these people that he just met. There’s something uplifting, aspirational and hopeful about that. I think Anthony’s even more invested, because in Season 1 it’s a group of strangers; in Season 2, he’s coming into a family. He really gets invested in these characters and their storylines in a really significant way.

How do you make sure you’re casting someone who hasn’t seen “Jury Duty” Season 1 or who will recognize any of the actors?

Szymanski: We don’t like to give away all of our secrets on how we do it, but I do think it’s safe to say, we’re certainly not looking for people who are up on the latest pop culture or who have seen every episode of TV recently, or spend every waking hour scrolling through TikTok. Casting is tough. By Hollywood standards, we’re looking for people who haven’t popped yet, but it does also come down to “Was this comedian in a really popular viral comedy video that went around the internet all this year?” That’s dangerous, and maybe we can’t cast that person. That’s the type of thing our hero might have seen.

I recognized Lisa Gilroy from Season 1, and she’s been all over my TikTok with her comedy videos.

Eisenberg: Yeah, he did not know who Lisa was. We love Lisa. She was such a breakout in Season 1. For as small a role as she had, not being part of the main cast, we changed her look from Season 1 and what people expect of her. She’s such a chameleon that she disappears into a role in an amazing way. But yeah, that’s probably pushing the limits of how far we can go. Deservedly so, she keeps getting bigger and bigger.

Szymanski: Lisa was obviously playing a new character who is not named Lisa. When she was introducing herself to all the employees who came in, she shook Anthony’s hand and said, “Hi, I’m Lisa.” And we’re like, “Oh God.” Right away, she said her name to him. He just walked by, didn’t think twice of it. It worked. She literally admitted who she was to him, and we got away with it.

Eisenberg: “Hi, I’m Lisa Gilroy. I’m an actress!”

Did you worry about Anthony googling “Rockin’ Grandmas” or searching for any of the actors’ characters’ social media?

Szymanski: Well, I think Rockin’ Grandma’s is a small business, and has an appropriately sized website and social media presence, so I think we were safe there. The main difference between Season 1 and Season 2 is we’re creating a world and characters who know each other so much better than Season 1 when they were all strangers. So it’s a little easier to have Anthony go with the flow. When he sees everyone say, “We’re not doing phones on this retreat,” he follows along.

Eisenberg: We took almost three years between seasons. There’s a tremendous amount of care and preparation that goes into every one of these eight 25-30 minute episodes. There’s nothing casual about it. In the preparation, there’s an Instagram with multiple pictures of Rockin’ Grandma’s hot sauce. There’s a Triukas website. You have to build enough of an infrastructure so that the world is not just what he sees, but if he were to venture outside of it a little bit. The Rockin’ Grandma’s website looks like something that your 14-year old nephew made, and the Triukas website looks like you hired someone to pay tens of thousands of dollars to develop it.

Szymanski: In Season 2, the world build was so much bigger that it felt a lot more like “The Truman Show.” We have to build company histories. Instead of being in three rooms in a courthouse, we were on three acres of a campus. We had to be ready for him to go anywhere.

Eisenberg: You have to create backstories for the characters, and then the actors run with that. Then you have to create dynamics between the characters. This person’s worked at the company for three years. This person’s been there for 18 years. This person is above this person. There are inside jokes. There are things that existed before this person, but after this person. All of that needs to be carefully orchestrated, because at any point if Anthony says, “Did you always work in customer service or did you start as an assistant, or were you the secretary?” All the things that you might ask in a workplace, there had to be answers to everything.

Szymanski: One of the actors can’t randomly say, “We went to college together, and that’s how we know each other.” Then Anthony can mention that to the next actor, and they’ll be like, “What are you talking about? I don’t know.” And then all of a sudden, the whole show falls apart.

How did you get Sia to show up for the talent show? Did she know what was going on with the show?

Eisenberg: Sia absolutely knew what the show was. She was a giant fan of Season 1. A few of the producers have known Sia for a few years. So we reached out to her, and she was immediately on board and so excited to be a part of it. She and Anthony completely connected. I’d never seen Sia do that before, and it was just a delight. She had a blast with Anthony, and Anthony loved her and had so much fun with her.

After having James Marsden in Season 1, were you trying to land another celebrity for Season 2? Was Sia always your choice?

Szymanski: With “Corporate Retreat,” we wanted to be true to the world. We can’t just randomly have a celebrity who’s there all the time.

Eisenberg: James Marsden does not work in the warehouse of Rockin’ Grandma’s, and there’s nothing we can do to convince anyone of that.

Szymanski: Sia was our top choice, because it fits so well with the talent show. So that worked out perfectly. The tricky part is, normally when you have a guest star of Sia’s level, on a typical production you move everything else around to make it work for her however you need to. You’ll film out of order and do any of that. When we pitched it to Sia and she became interested, the tricky part was the one two-hour window that this will work for Anthony and she has to be there for it. But she was totally up for it.

You reveal in the finale how one opened car window nearly derailed the entire ending. Were there any other close calls that almost ruined the show?

Eisenberg: When we were doing the hypnotist show, we thought that somebody had left a script out. Again, in a normal show you’d call cut. You’d say, “Hey, someone left their cellphone, and we’re shooting a show that takes place in 1883. Can you take your cellphone out?” In this, it’s like, “What’s that page? What’s happening here? Oh, my God. Anthony’s right by there. Is there anyone who could get it? Is there a waitress who could race in and remove it?” You’re just watching, it’s like a trainwreck in slow motion. Finally, someone was able to move the paper, or whatever it was. But for three minutes, we’re all just staring at the monitors, like, “Please, Anthony, don’t look to your left.”

One of the most surprising moments in the finale was when Anthony convinces Doug to reject the Triukas deal and says “father to father,” because we don’t learn much about Anthony’s personal life or that he’s a dad. Did you know that when you were casting him, and did that impact your decision at all?

Eisenberg: It wasn’t a surprise to us. You’re interviewing them, and you’re getting as much information as you possibly can. It was not something we wanted to lean into and make it feel ploying in any way. That moment was really organic. It was close to what we had envisioned when me, Jake and the other EPs went away on our own company retreat to talk about “Company Retreat.” It was the most meta writing session of all time. The whole thing was, the hero is going to run down the hill and and stop this deal from happening. We had constructed it in a slightly different way, and then he said “father to father.” It took our breath away. It was so dramatic in such a personal way and really spoke so much to Anthony’s character that it so far exceeded whatever we could have possibly envisioned two years earlier. That’s what’s so fun as writers and creators of these worlds. There’s a danger to it, and you don’t know what’s going to happen. There are moments where you’re like, “How are we going to get them to search everyone’s rooms?” And Anthony’s like, “I think we should search everyone’s rooms.” And you’re like, “Did you tell him? Why would he offer that?” Those are real. Those are not moments that we constructed. We need the rooms to be searched. If Anthony happens to say it, great. But if not, these three people are going to come up with this idea, and then all of a sudden he says it. It’s remarkable.

Was there a more stressful moment on set than when you were shooting the finale?

Szymanski: Because Anthony’s a real person, and you never quite know how he’s going to react, it’s just tense every day. Even the little moments are tense. It’ll be something silly, like we’ve constructed an entire scene to happen outdoors at lunch. All of our cameras are hidden for them to talk at the lunch table. Then you’re just hoping that he’s walking back from a seminar and he’ll stop at the lunch table and won’t decide to take a nap or that a bee doesn’t fly by or he’ll go, “I’m not sitting outside today.” It’s silly stuff that becomes very stressful, because sometimes he knows the documentary crew cameras are there. A lot of time, he doesn’t know the cameras are there and that’s where you really need everything to work.

Do you have any other ideas in mind for a third season?

Eisenberg: When we first started doing “Jury Duty,” we promised Amazon that we would pull it off and shoot a full season of television, and that was maybe a hair of a lie because we didn’t know that we could actually do it and no one had ever pulled it off before. We only decided to do “Company Retreat” when we felt like we had this great idea and a storyline that we really want to tackle. Going forward, if we’re lucky enough that someone wants to pay us to do that, we need to make sure that it feels right.

This interview has been edited and condensed.