A six-hour CMO campaign exploded on LinkedIn and was shared by hundreds of marketers. The satirical video poked fun at cringey corporate tropes and leaned into some uncomfortable humor.
Air’s campaign was bold. It was risky. And it was also the company’s second-highest driver of website traffic for the year.
On SaaS Half Full, Lindsey Groepper sat down with Ariel Rubin, VP of Content at Air, the mastermind behind the satire, to find out what lessons other brands can learn from taking a leap into the pool of discomfort in their own marketing.
Break out of the boring
Most B2B SaaS marketing is safe, polite, and often forgettable. You know what else is great at creating safe content? AI.
Generic campaigns are a guaranteed way to blend in.
Ariel believes marketers need to take risks, but cautions against trying to replicate his video. You’ve got to understand the risk profile of your own company and toe that line.
He uses Jim Carrey in The Truman Show as a metaphor for finding your organization’s creative limits. (Spoilers ahead!) Carrey sails out in search of the edge of his world, and he hits that wall with his boat. Ariel says you locate that proverbial wall by experimenting.
“You gotta try. You gotta make stuff. You gotta see where people get upset or annoyed or frustrated or feel like you missed the mark. There’s no way to know if you don’t get on the boat..” — Ariel Rubin
Rather than settling for sanitized or AI-generated filler, aim high with every campaign. If you feel safe and comfortable when publishing content, you’re likely producing work that won’t break through.
Measuring success is hard
Hard numbers don’t entirely capture a campaign’s success. Ariel says he likes to look at a combination of the classic organic engagement metrics, like earned media, views, follower growth, engagement rates, and full-funnel multi-touch attribution.
But he also measures “ineffable, vibes-based KPIs.” He says conversation is the best possible outcome. You know a campaign has momentum when friends text you out of the blue, colleagues share unprompted Slack screenshots, or industry peers post about it.
One of our PANBlast VPs commented on LinkedIn that they didn’t “get” the six-hour CMO. Ariel’s response?
“To me, that’s the dream. I don’t want everyone to be like, “You’re the best marketer. I want people being like, “I don’t get it. Why do we do this? Is this good? I want them thinking critically about what I’m doing and asking those questions.” — Ariel Rubin
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Episode Transcript
This has been generated by AI and optimized by a human.
[00:00:00] Ariel Rubin: my advice to people who are like, “How do I get my CEO to– How do I convince my…”
You should quit.
[00:00:05] Lindsey Groepper: Yeah
[00:00:07] Ariel Rubin: I don’t think in 2026, if you’re trying to convince your CEO why you need to like have a voice that’s unique and break out on X or LinkedIn or Instagram or whatever, like you’re kind of done. Like
that person doesn’t wanna win. And so like if you wanna win, you gotta go to a place that wants to win too. Hi, and welcome back to SaaS Half Full, the only show serving B2B SaaS and AI marketers. I’m Lindsay Gropper, EVP at Pan Blast, and I will be both your host and bartender today. I had a killer conversation with Ari Rubin, who is the VP of content at Air.
[00:00:41] Lindsey Groepper: He is the mastermind behind several viral brand campaigns, including the recent six-hour CMO hire that I’m sure you saw come across your LinkedIn feeds. Now, Ari really pushes the envelope in terms of risk on his brand campaigns. They create entertainment value in [00:01:00] all of the campaigns that they publish, and we’re gonna talk about how you can understand the risk profile of your own org and kind of where to draw that line.
that if you care to, grab a drink and join me as I speak with Ari
Hey, Ari. Welcome to SaaS How Full.
[00:01:13] Ariel Rubin: Hey, thanks, Lindsay, for being here
[00:01:15] Lindsey Groepper: I’m excited to have you. Jake from our team approached you. He follows your work, follows the brand, and said to me like, “Hey, what do you think about having Ari on the show?” I’m like, “That would be killer.” So glad that you accepted. you did schedule an interview pretty quickly, which is awesome by and large, except that means that we were not able to send you a drink kit.
So what I do on this show, Ari, is I share a drink with my guests, but we couldn’t get you one in time. I am drinking though, alone, which is something I do often on this show, and it’s
[00:01:45] Ariel Rubin: I love that
[00:01:46] Lindsey Groepper: AM on a Wednesday, people. Here we go. And I’m drinking a screwdriver. are you sharing a beverage of any sort with me today?
[00:01:54] Ariel Rubin: I’m not, but I, I’m really impressed that you’re drinking a screwdriver at 10:45 on a Wednesday [00:02:00] morning. I love that
[00:02:01] Lindsey Groepper: I will tell you, I’ve been doing this podcast for six years and, uh, the shtick has always been the same. And there’s only been two times in six years that I haven’t drank. And one, was during, it was like the very beginning of COVID, and I had it and felt terrible, still did the interview.
And the other time, I– it was on a Monday morning, and I’d had the stomach flu over the weekend, and I just like, I just couldn’t f**king do it. I was like, I woke up and I was like, I can barely eat a cracker. I can’t drink right now.” but other than that, I do the thing. So,
[00:02:32] Ariel Rubin: Oh my God. I didn’t realize it was
[00:02:33] Lindsey Groepper: it is
[00:02:34] Ariel Rubin: cheers. I, I’m drinking in spirit with you. I couldn’t, I couldn’t risk or drink a screwdriver. I don’t know when the last time I’ve had a screwdriver is, but I respect it. I really
[00:02:43] Lindsey Groepper: you. You know, the mimosa gets a lot– most of the love as the morning drink of choice, and I prefer a screwdriver on ice if given the, the choice and opportunity. So, uh,
[00:02:55] Ariel Rubin: you. Good for you
[00:02:56] Lindsey Groepper: thank you. Welcome to SaaS Half Full. we are [00:03:00] gonna cover a bit, quite a bit today. most people are gonna be familiar with the incredible, recent marketing campaign you did in August with the six-hour CMO.
We’ll dive into it a little bit. For those of you that after this wanna learn more, literally just type in Air and six-hour CMO. There’s a lot of press that was garnered from it. there’s no shortage of information you can get from it. But, you take risks. Your team clearly trusts you. You take B2B, which is often B2 boring, make it interesting, blend entertainment, make the brand entertaining.
So we’re gonna talk about that, um, and dive into all that. But before we do, Ari, I wanna give our listeners a bit of an understanding of who you are and your background. You have an interesting background. when I was diving in, I did not… I, I expected to see before Air, more B2B SaaS, more technology, and I did not find that.
So talk us through your journey, because you also went to school for something [00:04:00] completely different than where you are. so just talk us through a little bit where you, your journey, and then also please do quick elevator on Air, um, and your role there.
[00:04:09] Ariel Rubin: Yeah, sure. Well, thank you so much again for having me. It’s an, it’s an honor to be here, and I’m, I’m drinking a screwdriver with you, uh, spiritually. my name is Ari Rubin or Ariel Rubin. I go by both. I actually never even used to go by Ari, but when I joined Air, I thought the email address would be ari@air.
And I thought that was very funny.
[00:04:28] Lindsey Groepper: Very clean
[00:04:29] Ariel Rubin: I just go by Ari here. It’s like stuck. But,So yeah, I joined Air five years ago, actually, and it’s been about three years in which we’ve been kind of– I was the director of communications, and I did that for about a year and a half, and then transitioned and pivoted over to the kind of the content side.
And we have built out this sort of internal agency at Air that I’m, I have the privilege of, of leading, uh, as the VP of content now. for those who don’t know, Air is an agent for creative tasks, essentially a central source of truth for our team’s visual assets, photo and video. basically, uh, sort of [00:05:00] Dropbox meets Frame.io with a sort of the super intelligence of a Claude or ChatGPT.
it’s a super powerful tool that, 3,000 brands use and 35,000 people use every day. and when I joined the sort of pre-AI halcyon days, it was like the same– the sort of question that was asked of me, which I thought was really interesting, was like, “How do we create a real brand here?”
Like, we’re not– They didn’t hire me to do marketing. I’m not a particularly effective marketer.performance, life cycles aren’t really my background. the idea was we have these customers who are creatives, and we really want to understand and know them. And so we wanted to hire someone, they wanted to hire someone who kind of like spoke their language, I think.
and we realized quite early on that, yeah, we could like target people and kind of meta ad them to death. But there is a more interesting and maybe a more powerful play to, to get them and win them over, their hearts, uh, and minds. And that’s what we’ve attempted to do, uh, to varying degrees of success.
My background, uh, as you mentioned, is not in tech or B2B at all. This is the first B2B job I’ve had. I didn’t–
I find the challenge [00:06:00] of B2B the most unique ’cause it can be quite dull. I find it an endlessly interesting opportunity to try to make it compelling. I find that really fun.
[00:06:09] Lindsey Groepper: Yeah. And your, your first, jobs were on the humanitarian side, the nonprofit side. That, that matches like what you went to school for, philosophy, religious studies, and then master’s in human rights. but you took that and went more of the comms and creative and storytelling route. Where did that, like, creativity unlock?
You didn’t study comms, you didn’t, you weren’t graphic design, you, you weren’t in media studies. It was that more of that humanitarian side. So where, like, when did that creativity part unlock for you and where you thought, “I can do both”?
[00:06:43] Ariel Rubin: Yeah. I mean, I was always really ana– I mean, my original– originally I wanted to be a journalist. That was like my dream job. And I, I went to– When I went to school and studied, especially my MA, I did human rights in London, and development. And I, I moved to Uganda after that, actually, and I worked at a [00:07:00] Ugandan newspaper.
and I wrote for places. I wrote for Vice Magazine, I wrote for Huffington Post. Like, I wrote for real publications, international publications. But I, realized, and this was like 14 years ago, that there was no money for me to be made, and I was not a good enough journalist to get one of the few jobs that existed.
But I loved storytelling. Like, I loved being in Uganda and, and running around and writing stories and shooting video, like with my little camera at the time. And that was really addictive to me. And so I realized that there was a role for that, and that role was like… And this is early, like early social media of like pivot to video Facebook 2009, 2010, 2011 was like cool.
Like there’s this, you know, young millennials at the time were able to like, you know, create content with their phones or their cameras and post on the internet, and that was like very revolutionary. This was like Arab Springs, Twitter, AOC becoming up, like that’s the era where I became kind of the idea of a journalist becoming a creator started.
And so I just started making stuff for these, these companies, these organizations like the [00:08:00] UN, and they were really, they were really into it. And that’s sort of how I got my career started.
[00:08:04] Lindsey Groepper: Okay. how do you personally like pull meaning into your work when you came from more of this like humanitarian do good side that to me, seems like it would be easier to pull out my, you know, the value that I’m getting from that meaning.
How do you find meaning across these different industries, leaving something that’s so directly tied to, humanitarian efforts?
[00:08:26] Ariel Rubin: Well, I think I, one, I became pretty jaded of the humanitarian space after about– You see a lot of things there that are not,
[00:08:32] Lindsey Groepper: Interesting
[00:08:34] Ariel Rubin: you see like how resources are allocated or what good you’re actually able to do. So there is like a s– And not to say that organizations like the Red Cross and UN aren’t, I think, really powerful and effective, but you do become a bit jaded, or I did at least.
And then similarly, I think once I went to– Part of it is that I don’t– I try not to derive too much meaning out of… My work is just one thing I do. and I try to use that to find meaning in other spaces and whatever. I mean, [00:09:00] I– not to get political, but I’ve been involved in certain causes, which I, think are great.
But, um, so that’s, uh, uh, part of being outside of the– When that’s not your full-time job, you’re able to, I think, give more. I mean, also like the other thing is like I, I didn’t have kids when I worked in the UN. Like I just ran around Sudan, and that was really interesting and kind of scary and really fun.
And then I had children and realized I no longer wanted to like do that. The other part I will say is like, and this is applies to the work I do today, which is like I derive meaning out of creating stuff that people love.
I’m really competitive with myself and with what I see out there that’s good. And I, I wanna produce a world-class, you know, world-class content, and I wanna be best– Like, I wanna be the best at it.
And so when I see other brands do that, whether they’re B2B or not, like I’m– feel like we’re competiting, we’re competing with everybody. I don’t just wanna be like the best B2B brand. Like I, I wanna be the best brand. So like that means I’m competing with Nike and Apple and Netflix and Amazon and, and yes, Ramp and Clay and other, you know, [00:10:00] B2B brands that are doing a really powerful job.
Like there’s such a cool, such a fun environment to play in that I get more personal meaning now, I guess, out of like competing with, really with myself, but like trying to win. I like that.
[00:10:14] Lindsey Groepper: Yeah. So we’ll dive into that. So you have created this, this place at Air where entertainment is the brand. It’s not let’s be a brand and then maybe make some interesting content. It’s entertainment is the brand. and there’s definitely things that we have all seen that are products of that, um, that indicate that that is working for you.
but for a lot of our listeners, the appetite for risk may or may not be there. there’s certainly a risk reward. I mean, the, the last, campaign with the six-hour CMO that you did, that was risky in that there was politically incorrect, a little bit culturally insensitive, but it worked in a way for the brand and for you, um, because it was clearly satire.
And I [00:11:00] always like to say, you know, you’ve made it when, um, you have the dissenters and vocal minority come out of the woodwork and be piss- you know, pissy about whatever it is that you did.
[00:11:08] Ariel Rubin: Tør du det?
[00:11:09] Lindsey Groepper: that is something that works for Air. But what– How do you know, like going into an organization, and I’m sure you had varying degrees of risk profiles with the other orgs that you worked with, but how do you uncover like what the line is when you go into a place?
Or even if you’re there now and you’re like, “Man, we, we need to do more and better,” how do you establish that line?
[00:11:31] Ariel Rubin: The best metaphor for me on is the film– Have you ever seen the movie, “The Truman Show”? Remember “The Truman Show” with Jim Carrey? Like, and he’s– Jim Carrey’s like an actor, for anyone who hasn’t seen it, he’s, he’s in a film set, but he doesn’t know it. And it’s like a really crazy f- I, I love this movie.
But at the end of the film, Jim Carrey is sailing out trying to find the wall of his like world and he finally hits it with his boat, for the spoiler alert. And like he hits the wall and that’s it. Like his world is over. And For me, that’s [00:12:00] what this job is, is I’m always trying to find where that wall is.
And I think that’s the job, by the way, like I think that’s the job wherever you work in creative. and that doesn’t mean that like, that I think everyone needs to be a risk taker or, like a brand with like a voice. It’s like, you know, like I don’t think that that’s the case. I don’t– It depends who you’re– Like this works for us because we’re selling to people that are very much me and actually a lot of people I think in your audience, right?
Who are creative people who work on marketing teams who really wanna be making stuff that allows them to be really creative and fully self-actualized. And the metaphor of error being the tool, the home that lets them make their best work is what we wanna convey with every campaign we do. You may not like the campaign, you may love it, you may hate it, but you will, I hope, be like, “Damn, they took a shot.”
Like I’m a marketer. I, I s- I wish I could take a shot. Like maybe I will take a shot. That’s my hope. And I think that for every company, brand profile, person, team makeup, leadership, et cetera, you really wanna figure out where that line i- that the wall is. But the only way to find that is by shipping out [00:13:00] there.
Like you gotta, you gotta try. You gotta like, you gotta make stuff. You gotta see where, where do, where do people get upset or annoyed or frustrated or feel like you missed the mark or et cetera. Like there’s no way to know if you don’t get on the boat.
[00:13:10] Lindsey Groepper: Yeah, I agree. someone that you involved in your, um, six-hour CMO campaign, which is, that’s what I’m calling it. Is there another… Do you call it something else? Okay.
[00:13:19] Ariel Rubin: 6 Hours Evo, I love, I love it. Yeah. We also called it A- we called it the A- A- the Asian for Creative Tasks, but that was a more, uh, it was punchier.
[00:13:28] Lindsey Groepper: Yeah. Yeah. Okay. Well, I’m, I’m gonna go with six-hour CMO. I’m gonna… I’m looking down, I’m reading this because you involved, um, Tim Chiusano, I don’t know if
[00:13:35] Ariel Rubin: Yeah. Yep
[00:13:37] Lindsey Groepper: but when, when he shared it on LinkedIn, he was involved in the, the campaign, like actually seen in the video.
I really liked what he said about it because he said, “This is different. If nothing else, I hope it gives anyone in marketing out there a little more inspiration to be a bit more bold. Not like this, for the love of God, don’t try to replicate this. But also don’t be afraid. Even if you are the only one at [00:14:00] the table that’s like, ‘I kind of get it, I kind of don’t, this makes me uncomfortable,’ then maybe it’s exactly why you should stick around and give it a shot.”
[00:14:07] Ariel Rubin: Yeah
[00:14:08] Lindsey Groepper: There’s two things here that I really like about it is one, it’s don’t try and replicate something that already went viral.
[00:14:15] Ariel Rubin: Yes
[00:14:17] Lindsey Groepper: just never works. But two, this idea of being comfortable with, with being uncomfortable. Talk to us about, like, how, like when you launch these campaigns and this one specifically, I would imagine there was a level of like, “Well, sh*t, let’s see how this goes.”
Like, there, you are uncomfortable.
[00:14:37] Ariel Rubin: Definitely. if I’m comfortable, then I need to work somewhere. Like I am, I’m done. I’m out. Like I can’t… But I’m also disengaged and I’m doing bad work, and no one likes it. I’ve been comfortable before.
It’s, I have to leave a place when I’m comfortable. I have to either get fired or quit. I love living in the f**ked up zone of discomfort because then you know you’re maybe onto something. And you might not be onto [00:15:00] something. You might be onto like dog sh*t, but I like that… Tim’s amazing.
Like what a, he’s what a legend. Like he, I think he nailed it,as he does. Like that’s exactly the space we try to be in at Air, which is why I really, I mean, I’ve been here for re- This is the longest I’ve worked anywhere. And the reason I’m, I’m here is because I love that we put our money where our mouth is on this ethos.
It’s not just like some bullshit we’re like, “Oh yeah, creatives should create whatever.” Like no, we’re like, “Yeah, now we’re gonna f**king do it.” And you might hate it or it might suck or like it might not w- Like we have many campaigns that don’t do well. We have many campaigns that don’t rip, but we, what we do is we do them all the f**king time.
And we, we sh- Like every shot’s a moonshot. Like I don’t, I don’t put out shitty content and I, I don’t want to and I like, like I wanna be uncomfortable and I wanna feel really n- Like I love that feeling when it goes on the internet and you’re like, “Okay, f**k.
[00:15:51] Lindsey Groepper: Yeah. Let’s go.
[00:15:53] Ariel Rubin: let’s go.”
Like that to me is like the greatest, uh,
[00:15:56] Lindsey Groepper: And, and I would imagine for those of you listening, like [00:16:00] try and think of a time literally in the last year where you’ve put out a piece of content and did like the hold your breath thing. You know where you’re just like, you hit live and you’re just like, “Okay.” Like I, I bet most of us can’t think of one thing that we’ve done.
And I think part of the issue that’s compounding this is AI is, is really good at creating very nice, safe content.
[00:16:26] Ariel Rubin: Yeah
[00:16:27] Lindsey Groepper: It does even when you ask it to go bold, even when you say, “Make this spicier,”
[00:16:33] Ariel Rubin: Sure
[00:16:33] Lindsey Groepper: it does not. And I mean, even this is like on the personal side, but like my eight-year-old, he’s in the yo mama is so fat, so ugly joke phase with his buddies.
And so we… I was on with ChatGPT, and I was like, “Give us some like classic, you know, like yo mama jokes.” And it wouldn’t. I was like, I realize that we’re not supposed to talk about… I’ve had the talk with my son. We’re not supposed to comment on people’s looks. Like he knows not to actually say this to [00:17:00] anyone.
So like just let us have it. And she, w- she’s a she for me, wouldn’t do it. Like wouldn’t, would not pass that line. It was like, “Yo mama is so energetic.” And we’re like, “Wha, wha?” But like wouldn’t go there, you know? And it’s just you, so you can’t… You have to, use your judgment when it comes to what is a little bit off-putting, what has, is over line enough that you know it’s probably gonna piss off some people, but not so much so that it’s gonna piss off your entire ICP or half of your ICP.
So Ari, what is that? Like what is that, when you think about putting something out into the world that you know there’s gonna be some dissenters, that is gonna makes you uncomfortable, how do you weigh that with how is this gonna play with our ICP? for example, there was, uh, the six… Our CMO is Asian American.
I forget what the [00:18:00] holiday was that you tied it to. It was like Asian American Employee Appreciation Day or something like that.
If it was up to me, every month would be AAPI, Asian American, Asian, AAPI Month. Okay. So there was a lot, there were some, what some would consider culture insensitivities, and I’m sure that you have as part, in, in your ICP, you have Asian Americans. So like, how do you weigh that risk reward when it comes to your actual buying audience?
[00:18:26] Ariel Rubin: the joke of the, of the campaign with Eric was Eric is– Eric’s one of the, one of the most, I guess one of, like, the best and most famous kind of like living, like mar– in terms of marketing, like I’ve known Eric for years. He’s like my, he’s like on my Mount Rushmore of marketers. I just think he’s gen– he’s worked at every Gap, Snap, Nike.
He’s so funny and intel- and I’ve always liked him and he’s just, I’ve just, really looked up to him and I think he’s, you know, he’s lovely. He was like: “Look like I wanna do something, you know, fl- but I don’t wanna do some bullsh- like some same thing with you. Like, let’s do something fun.” Like, and I think like, again, Air being able to garner the [00:19:00] reputation as a place where marketers come to, like, to me, like forget the adoption of the tool itself.
if I’m successful as a brand marketer that people are coming to me because they wanna like, he’s like: “What can we do together? What can we brainstorm? What can we come up with?” And so to me that’s already– And it’s like, sure. Like, yes. is there a, an issue of cultural, uh, insensi- maybe, but like, I don’t know.
This was a campaign that was written with, produced by, and starring an, a, an entire cast and crew of Asian colleagues and, and, and talent. And like the joke is on me in this f- like the film is, it’s pu- it’s punching up my– I’m the moron and the rube and Eric and Charles Xu, the comedian we worked with, and, and J- Jakey Cho, like these three guys are just like hilarious and come off, I think, like really rad.
And Eric is like one of the also like a huge advocate and like a really famous advocate for AAPI, you know, causes. And so like him playing against character and playing this role is so funny and unexpected. And I think again, like to me, I had no wor- I [00:20:00] didn’t really, I had no concern about it. I mean, I had some sure, I had like some anxiety about it, but I didn’t think it was gonna be, um, problematic because I think it was the spirit of it and the kind of concept of it and like the production with it was, was tied into like some really funny truths and like, I think a, the, a crew that was really able to like convey that.
[00:20:17] Lindsey Groepper: Yeah. No, it, it was awesome. am I right to say that that has been your most viral campaign?
[00:20:24] Ariel Rubin: No. It ha- not even close.
[00:20:26] Lindsey Groepper: Okay. What
[00:20:27] Ariel Rubin: It’s been our most vi- it’s– I mean, we did, we’ve done stuff, we, we did a video with Kareem Rahma from Subway Takes and The Rizzler, which went probably like 15 million views or something on Instagram at this point. I mean, huge. I mean, like we’ve had things that have gone bigger, wider.
I think the thing about the Totav one that I love is that it’s, it hit the ICP like with, like, with a bullet. Like it was crazy. Like I’ve had stuff that’s hit 10 mi- this has hit every creative and marketer in that space in the way… And m- I mean, most have heard of it or seen it, but we’ve done a ton of– I mean, I’ve done stuff, we did [00:21:00] things with Maury Povich, with the, you know, we’ve done stuff with Boy Thrones.
I did stuff with Bonnie Blue, the, the adults film star. That has all gone extremely viral, and gotten a l- gotten a ton of media. But this was like the most, I think, uh, maybe the sharpest, if I can say that.
Yeah
[00:21:17] Lindsey Groepper: has there been a that went too far?
[00:21:22] Ariel Rubin: Yeah, sure. I think the, the Bonnie Blue one was probably a little too… I don’t know if you saw that one. It was– We had to re- we removed a lot of it off the internet, but it was, it’s still on the internet. You can find on, like, there’s articles about it. It was in the Daily Mail. Um, but
[00:21:34] Lindsey Groepper:
[00:21:34] Ariel Rubin: I learned that we don’t work with porn stars or politicians. That’s the lesson. I just avoid porn and politics now
[00:21:41] Lindsey Groepper: Which like is making me laugh because it’s like that seems like pretty like, yeah. you shouldn’t even before you go there
[00:21:51] Ariel Rubin: I got to learn the hard way. So, you know, I’m a, I’m a visual learner, Lindsay, so I have to learn things
[00:21:55] Lindsey Groepper: Oh,
[00:21:56] Ariel Rubin: I’m not good at, I’m not good at lessons. Yeah, that was a [00:22:00] tough one, but it’s fine. I don’t know. People still reach out to me about it. I don’t know
[00:22:04] Lindsey Groepper: I know, I remember, I think it was Sheet@Digital, Tim, who then went on to work at Wunderkind, Tim Glomb. He worked, like Sheet@Digital way back in the day, uh, did something with Tommy Lee and his wife, who’s a porn star,like something around their event as well. So it’s like it has been done before.
Um, but
[00:22:22] Ariel Rubin: Death did one as well. Uh, Liquid Death did a really funny one with a porn star, about like, like f**king, unf**king the planet with plastic, like how
[00:22:29] Lindsey Groepper: Yeah.
[00:22:29] Ariel Rubin: f**ks the planet. Like, I mean, nothing is new under the sun. I don’t think I’m like that– I don’t think I’m particularly innovative here.
but you know, we
try.
[00:22:36] Lindsey Groepper: but yeah, but pushing the envelope. and it seems like you have, uh, an exec team that gives you a lot of autonomy, that trusts you. that’s not the case with everyone. how would you suggest that other marketers, if they’re like, “Okay, I’m inspired. Yes, I need to be doing more, being bolder,” to start to build that trust and that comfort level with their C-suite and with their [00:23:00] board?
do you start small? Do you start big? What do you suggest?
[00:23:05] Ariel Rubin: I’m sort of of two minds. I mean, I think on the one hand, the thing that I, I really love, like I said, I– what I love about working at Air and what I really… Is that Shane, our CEO, Tyler, our co-founder, CTO, they– it’s not like I gotta convince the team or there’s like we’re all, we’re on the same team.
Like they, they understand that why– that in order to break out in a really crowded market, you need to make some noise. Like this is not like that if your B2B company is gonna be successful and your venture-funded company’s gonna get more venture funding, like people need to hear about you. And they’re not gonna hear about you if you’re not saying anything or if you’re not doing it in a way that is grabbing their noise.
And that doesn’t mean that I think everyone needs to like work with a porn star or do something stupid. But I do think you need to think about for the audience that you’re trying to reach, what are the ways you’re gonna break through the noise? And I think there’s no daylight between me and our leaders at this business on like what needs– that, that needs to happen.
[00:24:00] Now, there’s a robust debate on what we do, of course. Like, do we have like, you know, we beat, we beat… They’re not just like, “Yeah, go for it.” Like, you know, “Go nuts. Here’s…” But you have to have that buy-in from the start. And I, I am honestly, like my advice, I say this a lot too, which is like my advice to people who are like, “How do I get my CEO to– How do I convince my…”
If I’m– You should quit.
[00:24:19] Lindsey Groepper: Yeah
[00:24:21] Ariel Rubin: I don’t think in 2026, if you’re trying to convince your CEO why you need to like have a voice that’s unique and, and break out on X or LinkedIn or Instagram or whatever, like you’re kind of done. Like you wouldn’t need to spend six months trying to convince some, some guy.
Like that person doesn’t wanna win. And so like if you wanna win, you gotta go to a place that wants to win too.
[00:24:42] Lindsey Groepper: No, totally. I
[00:24:43] Ariel Rubin: I don’t know.
[00:24:43] Lindsey Groepper: agree with that. Yeah. We, um, so at Pan Blast, we do PR for B2B SaaS and AI companies,
[00:24:49] Ariel Rubin: Yeah
[00:24:50] Lindsey Groepper: the marketing leads that I talk to in the sales process will say, “Well, okay, now I need to go, like, convince my CEO or make a case to my CEO to unlock budget [00:25:00] for PR.” And it’s like, we don’t want to work…
It’s like I don’t, I actually don’t even want to work with you now if I’m gonna, if we’re gonna be in a situation where the CEO inherently you had to convince him and it’s, he’s, hedging that like, “Okay, yeah, but like we, this better work.” It’s like it’s f*cking brand, and you’re saying he doesn’t believe in having a strong brand and telling a story?
Like, good luck. Let alone with us, you know, as a PR agency, but like, just good luck in general. That sounds like a terrible place to be.
[00:25:29] Ariel Rubin: I agree. Yeah, I think that’s– I wish to– Like, things move too quickly now. AI has changed how we have to go to market in such a profound and dramatic way that there’s just like… I used to say I would– If you’d asked me this question like three or four years ago, I’d be like, “Start with a small project, get the quick win, do the pilot, whatever.”
Like, I don’t believe that anymore, actually. Like, I would never, I will never go work anywhere ever again where they’re, like, not completely bought in
[00:25:53] Lindsey Groepper: and they’re like, “Let’s go, let’s cook, let’s try stuff, let’s move quickly, fail, whatever, but, like, go.” I love that energy at [00:26:00] a s- at in– That’s why I think I also really enjoy this space, is that there’s just such an incredible mo- forward-facing momentum that, uh, for some of the, the way my brain works, it, like, really fits.
Ari, I, I feel in the era that we are in now with LLM search that there’s a lot of CEOs that would look at this campaign, um, the six-hour CMO campaign and say, “Yeah, but did it change our position in AI search?
[00:26:24] Ariel Rubin: Did it index in the LLMs?” What do you say to that?
I would say to that, I have never had more CMOs reach out to me and reach out to this business than I have after that campaign, where people from extraordinary places– The ROI, if we need to look at it through the ROI of this campaign, has already paid off. It’s not an expensive ca- We didn’t shoot this with an agent.
my friend shot this. Like, we shot it– I wrote it. literally I starred it. Like, it’s stupid. Like, it’s not like we spent $200,000 and like… We shot this in a day, you know? on like a small camera. So like, I [00:27:00] think the, there are a lot of things you, you need to do to figure out your positioning on, on ChatGPT’s search results, and I don’t think your brand, your big brand plays are the ones that are gonna necessarily get you.
Although I bet if I search 6-hour CMO right now, I bet it comes up on chat.
[00:27:16] Lindsey Groepper: Oh, it would, but if you searched best,
[00:27:19] Ariel Rubin: Let’s see
[00:27:20] Lindsey Groepper: agentic creative platforms, does, does any of that show up? It does– My point is it does not. And point B is that, like, w- uh, we’ve lost the plot because we’re– we do deal with the same thing as, you know, we’ll have a client say or CEO say, “Well, why, why does that story matter?
It didn’t, it doesn’t show up in the LLMs.” And it’s like, you’ve lost
[00:27:42] Ariel Rubin: the wrong question. Yeah, for sure
[00:27:43] Lindsey Groepper: and so, but that’s like the world that we are in right now, which is like everyone is so over-indexed on does this impact my LLM visibility? And ultimately, it’s still like wherever your buyers are, be there.
[00:28:00] Whether that is, is indexing on LLM search or not, if it is a place that your buyers live, be there still. And i-i-it’s, but it’s, it’s infuriating, infuriating right now for anyone that touches brands like, like you and I, um, because that is the only thing that people are talking about right
[00:28:18] Ariel Rubin: Yeah. Yeah. No, that’s fair. That’s true
[00:28:21] Lindsey Groepper: and the, uh, so I, I want to stay on the measurement part a bit, um, is there are obvious metrics when things, and I’m using air quotes for people who can’t see, um, that go viral.
Uh, you’re, there’s views, there’s media coverage, there’s shares, all that stuff, but not every brand campaign that you put out is gonna have that virality. So how do you know when something works? Like, what are the yardsticks that you look at? And is it pipeline driving? Are you looking at that as a b- as a measuring stick?
Or how do you know something has worked?
[00:28:55] Ariel Rubin: Yeah, it’s a great question. I mean, I think, like, personally, like, I like to look at [00:29:00] a blended mix of the classic engagement metrics of every, of any campaign. Like, I can’t just say I, it feel like I can say I think it worked. I have to say, like, many people, you know, we don’t, I don’t put money behind these things, so I’m not, so I’m not boosting these videos.
So do people watch them? what’s the engagement rate of these videos? What’s the eng- you know, what is the conversation that’s generated out of this? What kind of engagement? Like, we look at LinkedIn as well, right? We obviously, like, there’s an any touch attribution model where people who have seen us do certain things, like, will they come through eventually down the funnel?
But, like, the tota thing, I’m not, like, the marker of success for that for me is not how much revenue driven from that campaign. although coincidentally there was a decent amount of that. I look at your basic engagement metric. I also do believe in, uh, and this is I think there is an in- sort of an ineffable vibes-based KPI, which is
Totally
when people…
You just know when it’s actually in culture versus when it isn’t. And you know that because your friends will text you when they don’t actually text or, like, [00:30:00] your partner might see it, or, you know, when my boss, like, I get screenshots all of a sudden coming in on Slack from friend- like, colleagues who are like, “Okay, my friend saw this.”
Like, she never, like, sees any of my… But, and when that starts to happen and you feel it, you’re like, “Okay,” like something is… And people are– Tim posted about that organically. I didn’t pay Tim, I didn’t even pay Tim to be in the video. Like, Tim just did it ’cause it was an idea that I pitched. And like, I think when you start building, like, the groundswell of that, there’s a feeling where it’s like, damn.
I mean, and also I, I don’t have PR. Like, that was all earned PR. Like, people reached out and like we did, then it was in me- and then it gets media. So, like, it becomes this thing where like, sure, I look at earned, I look at engagement, I look at views, I look at follower growth, I look at all those things, and we measure all those things per campaign.
We look at any touch attribute down the funnel. But beyond all that, I think there’s all those things and there’s this like sense of like how do we grade this thing? What’s the report card? Like how’d it feel? How did, did– Also, like did the company li- like I also, I really wanna make sure, especially with something that can be like a little hot button, like [00:31:00] did the company align with it?
Like and I, if I get a message from a colleague who doesn’t usually reach out to me saying like, “Hey, I loved this,” like, “This was really funny,” or like, “This made me really happy,” like then that makes me, that to me is like worth a lot. but yeah, I, I think it’s, I don’t know. I don’t have a great… I, I struggle with measurement.
there’s not like a s- I don’t have like
[00:31:15] Lindsey Groepper: All brand marketers do.
[00:31:17] Ariel Rubin: I know. I
know, But
[00:31:18] Lindsey Groepper: I, all of us do, and, it’s interesting because we all know that there is a good 30% of your marketing budget that’s dedicated to brand that you cannot attribute to direct ROI, give or take.
[00:31:30] Ariel Rubin: for sure
[00:31:32] Lindsey Groepper: We know that if you cut that, everything else suffers.
[00:31:36] Ariel Rubin: Yes, 100%.
[00:31:37] Lindsey Groepper: And even despite knowing that, we still are trying to prove the value of brand dollar in, dollar out to, whether it’s a CEO, it’s a board, or sometimes even, even a CMO.
[00:31:49] Ariel Rubin: Totally
[00:31:50] Lindsey Groepper: but in, it’s frustrating because this has been, I mean, you know, I’ve been in PR for 20-plus years, and it’s been, it was the same then, it’s the same now, despite all of the [00:32:00] advanced analytics that we all have. Um, but we all know this, but inherently still are asked, “But what ROI did it drive?” It’s just like, can we just stop trying to measure brand?
Ju- ju- Can we just, just stop
[00:32:11] Ariel Rubin: preach. I mean, you’re preaching to the choir here. I, I remember, it– I will say it did get, it was, I think, the second highest website driver of the year was this campaign. But
[00:32:21] Lindsey Groepper: That’s something.
[00:32:22] Ariel Rubin: that’s something, but I, I don’t know. That’s not why I do it, but yeah, I’ll take it.
[00:32:27] Lindsey Groepper: I know. well, is there anything else that, uh, you want to talk about that we didn’t cover?
[00:32:33] Ariel Rubin: I don’t think so. I mean, look, I, I’m really happy that this campaign resonated and made its way to, these places. Like I– In fact, like I think it was funny ’cause I think Jake, I don’t have to call him out, but I think he also– I don’t think he liked the campaign very much, and we were de– I think we fought.
We got into an argument about it
[00:32:47] Lindsey Groepper: That sounds like Jake.
[00:32:48] Ariel Rubin: And I– But that’s– And I think I wrote this to him, I- if I’m not wrong, it was like– I was like, “To me, that’s the dream.” Like, the dream is people– I don’t want everyone to be like, “You’re the [00:33:00] best marketer,” like, “Great work.” Like, I want people being like, “I don’t get it.
Why do we do this? Is this good?” Like, to me, like the– If I’m engendering– Again, for marketers, I want these– These are the people I wanna reach, and I want them thinking critically about what I’m doing and asking those questions. And so for me, like that conversation generated is the best possible. I don’t want everyone just hating it obviously, but like people genuinely defending or arguing or beating it up in their heads, to me, that’s the best and I really appreciate.
So I’m just grateful that he reached out and that, that you, you had me on and, uh, it’s a pleasure and an honor to talk about. I’m glad it’s starting to resonate
[00:33:33] Lindsey Groepper: Yeah, absolutely. well, I know you don’t have a drink, but I do end every episode the same way, which is I ask my guest if they have a favorite or signature toast to send us out
[00:33:44] Ariel Rubin: Wow. I’ll just say, uh, I always like to say, Never above me, never below me, always with me.
[00:33:52] Lindsey Groepper: Love that one. Perfect. Cheers.
[00:33:55] Ariel Rubin: Nice to see you. Thank you for having me
[00:33:57] Lindsey Groepper: Yes, absolutely. It was great to speak with you. [00:34:00] Thanks so much, Ari
[00:34:01] Ariel Rubin: Pleasure, Lindsay
[00:34:02] Lindsey Groepper: thanks again to Ari for joining me on SaaS Half Full. I loved that conversation, liked to pull back the curtain on the six-hour CMO campaign. Super interesting. Hopefully it make you think a little bit differently about your own brand campaigns and when was the last time you truly felt uncomfortable before hitting the live button.
We always appreciate the listen. Until next time, bottoms up.