The Future of Creative Work with Patrick Holly, Executive Creative Director at Upwork


By Assemble

November 2, 2022

Patrick Holly is the Executive Creative Director at Upwork, where he leads a global team comprised of 80% freelancers to deliver Upwork's vision for the future of work. In this interview we discuss his experiences launching a content platform with Steph Curry, understanding a brand's storytelling potential and, of course, what the future of work looks like for the creative industry.

Find this episode on Apple, Spotify or wherever you listen to podcasts. Also available at Creatives Offscript.

Nate Watkin: Welcome to our show, Patrick.

Patrick Holly: Thank you so much. Happy to be here.

Nate Watkin: Really excited to talk to you. I mean, all things future of work, you know, creative teams, how the world is evolving, this is stuff that I live and breathe every day. So really excited to have a lot of questions around that. But typically on this show, we like to learn a little bit about your story first, how you got to where you were. So I wanna start off with a question. What did you want to be when you grew up when you were a kid?

Patrick Holly: I wanted to be I wanted to be a doctor. I <laugh>. Long story short, I grew up in a, in an environment where it's like you become a lawyer or a doctor or nothing, <laugh>. And so my dad was in law, so I thought I'd rebel and become a doctor. But in college I realized that I hate chemistry. And so <laugh>, I, at the same time that I found out I hated chemistry, found out that you could be something that wasn't a lawyer or a doctor. And that thing could be creative. And so I ended up I think it was three years into my college career completely shifting gears and doing a four year coms degree, about a year and a half. So that brought me to at least the, the, the front door step to where I am today.

Nate Watkin: That's super interesting, and I think you're the first person I've interviewed that, you know, was going to school for something as opposite of the creative industry as becoming a doctor or a lawyer, and decided halfway through your, your educational experience that you wanted to become a creative role. How was that? And I think from there, you initially stepped into PR role was your first job, Is that right?

Patrick Holly: Yeah, that's right. I, I actually, I was down in, in Philadelphia at a party of all things go figure in college at a party. But I met somebody there who she said her major was music industry management. And I was like, it blew my mind that that was like a major someone would do. Because I always loved music. I, I, I love kind of the creative field, obviously. And so I just started badgering her. I was like the most annoying person you could ever have met at a party, cuz I wouldn't like, like leave her alone. I was like, Tell me more about how you do this. And she ended up introducing me to a a really wonderful woman named Susan Zimmerman. She goes by Susie and she she started a back, way back in the day.

She started a PR firm called Magnum PR. And she was, you know, instrumental in you know, acts such as Nine Inch Nails and Marilyn Manson and The Prodigy. And she was gracious enough to take me under her wing as a as a pr a writer. And so I worked alongside her and, and her team to help people know who the hell we're trying to promote. But since I was, I was at the bottom of the barrel and totem pole and everything else in that office, I was given the things no one else wanted to work on. So the first thing I ever worked on was the Jim Rose sideshow which is like one of those sideshow things you see at a circus where like, guys hammer nails into their faces and like lay on, you know beds of snakes and stuff.

And, and that's what I was pitching, that that was my, my first ever writing gig was pitching the Jim Rose sideshow. I, I, I imagine if I were to do it again, it would be a lot of fun. I think I was just like really happy to just kind of like be involved in something that was creative and and be doing it in a place like New New York City that I was like, you know, just in awe, totally stoked. But I feel like it would be a fun brief right now to go back and revisit, that's for sure.

Nate Watkin: And so you start in PR then you got into copywriting, eventually worked at R/GA, and then Apple. Just tell me about that stretch of your career and what you discovered about yourself during that time.

Patrick Holly: So yeah, I, I, the, the bridge that kind of brought me from working in PR to working in, in creativity was my mom actually found a flyer at my school for this thing called the, the Portland Advertising Federation Collaborative. And it's basically where you you apply and they, they pick two writers, two art directors, two designers, and two you know planners or aspiring, you know, planners, writers, art directors from graduating classes around the country. And so I ended up getting one of those two seats for a writer based on a completely fabricated book that I just pulled outta my ass. So <laugh> that was, I was like, Okay, cool, maybe this stuff is easy. Turns out it's not. And so I, I was lucky enough to start working at a bunch of different shops in Portland just as an intern for them.

And then ended up moving up to Seattle for a quick stint and, and met a woman named Mira Crisp, who was my my one of my creative directors there. And she kinda took me under her wing, and when she went to rga, she took me with her. And so that brought me to San Francisco, was working there and, and really kind of got a, a full fledged look at what agency life was like which, which is which was really fun, honestly. Agencies are a cool place to be, especially when you're a junior creative. I mean, you basically live there, so thankfully they are a cool place to be. But yeah, I ended up working on a bunch of different you know, fun tech-based brands. I mean, it was a RGA San Francisco, so, you know, a lot of the clients there were tech based.

But ended up parlaying that into, into a gig at, at Apple because I, the last client I worked on at RGA was was, was helping to name and brand Beats music, what ended up becoming Beats music. And well, as the story goes, Apple ended up buying Beats music and folding it into Apple Music. And then and, and to do that, you know, they needed to kind of do a whole lot of rebranding and, and kind of strategic thinking around, you know, what their voice was gonna be and all that kind of stuff. And, and so I was actually through a, through a good friend Ke Smith who worked at Apple, he brought me in to do an interview and, and ended up going well. And I helped write a lot of the copy that you know, was to you know, merge those two brands and help, you know, Apple become you know, they're very cool, especially not today, but at that time, especially iTunes didn't see themselves as such, and they were, especially up against a brand like Beets, they, they needed a kind of a lot of you know, legwork around that.

So I ended up being one of the people who put that legwork in to to try and you know, meld those two brands into one you know, one Apple music as it is today.

Nate Watkin: Yeah, cool project to work on, really. And I think it's come out well, right?

Patrick Holly: Yeah, no, it's, it's, it's done pretty well. Yeah,

Nate Watkin: <Laugh> and I, I also saw that you have a photography background, is that right?

Patrick Holly: I, I have a photography background, like the cook in route. TUI has a background in, in cooking <laugh> where essentially like, I kind of look like I know what I'm doing, but there's someone else behind the scenes really actually doing it. And I kind of fell into to photography and it was, I was actually working with, I was working with Steph Curry for, for a number of years, helping him build a content platform to address his, his fan base in China. And through that, you know, we needed a lot of assets taken. There was no one to shoot it, so I ended up basically self-teaching how to shoot. And then as luck has it the same representation that represents Steph also represents Gianni onto De Kupo who is very, very wonderful gracious individual. And we had a great time together.

We ended up spending about two weeks or so together in China. And then after that his agent Alex ended up asking me, Hey, we need to do this campaign for it was a, a deodorant company. He's like, Do you wanna shoot it? It? And I was like, I mean, I guess <laugh>. And so I ended up like basically learn, like calling all of my photography friends, being like, Can you please teach me how to do like, proper lighting and how to, you know, everything, literally everything. And so I ended up shooting that, that that campaign for Giannis. And funny story, the one of the photos I actually took of Giannis that day is how I met my wife. She ended up seeing it on the explorer page of, of Instagram. And and she, she slitted my dms <laugh>, and she asked me out for a drink to which I obviously said yes. And and here we are today. But I wouldn't say I have a background of photography, I'd say that I, I've dipped my toe in and they're obviously much more talented folks out there in the world than me, but I just kind of I grabbed a paddle and road, as they say.

Nate Watkin: Yeah, there, there's so much to unpack. There's so many stories there. But I wanna start with Steph Curry. How did that come about? How did you get connected with him and what were you creating together

Patrick Holly: After, after Apple? I kind of wanted to get back into the into the, the, the agency world. I felt like I was still kinda a young creative. I didn't necessarily have you know, the breadth of experience that I, I kind of wanted before I went brand side. And so I wanted to go back into the agency world, and I wanted to start kind of like grinding again and, and, and starting to, you know, make work for different brands. So one of the recruiters from RGA ended up going over to AKA qa and she ended up reaching out and she's like, Hey, do you wanna help work on the the Jordan brand, AKA Q qa? I was like, Absolutely, I do 100%. And so that's what I did. And I went over there and, and was working with some really great creatives Dave Ruiz and, and Jan Bartowski in particular.

And I was working with them to do a, a content platform well, to do a lot of things, but one of them was a content platform for, for the Jordan brand. And so at that time, I ended up taking a motorcycle ride with with a guy who he was like the, the boyfriend of, of this girl who, the girl I was dating at the time was shooting. Cause she's actually a photographer, <laugh>. And and we ended up going in this motorcycle ride, and I'd never met the guy but we were at a gas stop and, and he was like, Hey, I really need to find a place to go watch to like a te to watch basketball. I was like, Okay, cool, man. Like we're gonna be, you know, we're in the middle of nowhere right now.

We were just going through like Yosemite, but let's, let's go find a place. And so we had to find this tiny little bar, it's like the only bar in this tiny little town. And we go in and he like sprints to the door. He was so excited. And I'm like, Okay, like maybe he has to go to the bathroom, or like, maybe he's just really into basketball, Turns out super into basketball, and particularly super into Steph Curry. And I was like, you know, looking at him, it's kind of in awe at how stoked he was about like this game and how invested he was. I was like, He must have like, his life savings on this game or something. Like, there's no reason why someone would be this excited. But then, you know, obviously whenever you meet somebody and you're kind of spending those first few hours with him, the conversation of, Oh, what do you do comes up.

And he asked me, and I was like, Well, you know, I work for this ad agency. We're doing a content platform for the Jordan brand right now. Like, what do you do? He's like, Oh, I work with Steph Curry and I'm building a content platform with him. We should probably talk. And so that led to me getting introduced to staff and his team and, and spending two years working alongside them building this platform, capturing content for it, and, and creating what ended up being one of the first celebrity led content platforms in, in in China.

Nate Watkin: Wow. Yeah. I I believe that was built on WeChat, right?

Patrick Holly: It was, it was built on WeChat. Yeah. We wanted to use something that was like didn't require somebody to download a whole new app, you know? Mm-Hmm. <affirmative> and WeChat being the most ubiquitous app in in China, It felt like a, a pretty a pretty easy decision.

Nate Watkin: And so, just looking at your resume, I mean, you've worked with so many amazing companies from RGA to Apple, Uber, Harley Davidson how do you, how do you describe the, the way that you work? I mean, it seems like you are touching so many different creative outlets throughout your career, and you're, you're not that old, right? Like, you've, you've been at a lot of different places. So how does that work?

Patrick Holly: I wouldn't necessarily suggest that it runs you pretty ragged <laugh>, but but my kind of thesis on, on, or like, kind of like my North Star when it, when it comes to determining, you know, next moves and and all that kind of stuff is really is there a story to tell? Like how, how deep is the, is the well for, for creative storytelling? And for that I look at the core of each of these brands. And so, like, if you look at all the brands that I've worked for they, they tend to have a pretty deep, well, if you will. So for Apple for example, it's all about, you know, the narrative is about creativity and in terms of Apple music was like creativity and discovery, which are like really rich territories to play in. If you think about Uber it's all about connection, connecting people connecting people to each other, to their cities, to goods and services, whatever.

It, Harley Davidson is all about freedom, which is, you know, as American as apple pie and also a pretty deep well but the one that was most exciting to me was, was my current job at Upwork, which is it's about, about about work. You know, all of those things that I just spoke about are compelling and and rich territories to dig into. But when you think about work it, it kind of, it trumps all of them. And, and that, you know, comes for many reasons, but you think about work everybody does it. Everybody has, you know, a, a, a deep tie to it for the most part. Some people, including myself, even define a part of their personality based on what they do for a living. And so that's a really, really fucking deep well <laugh> to pull from, and it allows us to make everything from you know we made our own coffee last year.

We ended up winning at ADC for that, which is awesome. To making, you know, our most recent campaign that features a, a dead CEO who's singing a musical about how the old ways of working are dead, you know? So I think, like for me, everywhere I look, I look for like, how deep is that? Well, and, and also at the same time, how willing is, you know, that organization to dig into that? Well our, our cmo, Melissa Waters, when she came on, her and I had a a one-on-one like the first week she got here, and she was talking about how great work is made on a stool with three legs. The first one is, is a brand worth talking about. So that's really like that. Well, right. The second is a team that can make great work and which is my responsibility, <laugh>.

And then the third is is a permission structure throughout the organization to make that great work. I think she just said something to the effect of like, Welcome to the third leg of the stool. Which I was like, Sick. You're, you're the best <laugh>. But, but but I really look for, I I, it took her kind of like saying that to realize that, Oh, that's what I've been looking like. That's how I kind of make my, my my, my judgments on, on kind of what the next move is and, and my trajectory professionally, if you will.

Nate Watkin: Yeah. And let's, let's come to the president here and, and talk about you getting a job at Upwork. Super interesting story. I believe you were working as a freelancer on Upwork as a creative director to help them with their rebrand. We'd love to hear how that came about.

Patrick Holly: I have been a serial monogamous with all of my like, career choices up until that fateful day, I decided like, freelancing is what's up, <laugh>. And I wanted to you know, I was kind of, I was staring down the barrel of having to move to a city. I didn't want to for a job, which is, you know, something, I had done a dozen, literally a dozen times before that, and I was kind of like, Fuck that <laugh>. I want to do what I want to do. I feel like, like I want to finally put down roots somewhere that I want to be. And my wife and I always wanted to move to Austin, which is where we live now. And so that's what we did. And my first client was Upwork, and, you know, what a, what a fitting kind of first client to freelance for, I suppose.

But I came on and that was for, as you said, to help with their rebrand. But I think it was like two weeks into me starting the ECD at that time. He left for a job at Google. And so Amanda Leech Ruby, who was my, my boss at that time, now she's, she's my partner. She's absolutely fantastic. The VP of of brand at Upwork, she was like, Hey, are you interested in interviewing for this job? It took me a second. Cause I, I was, I was kinda like, I don't because I, I really wanted to embrace this, this world of freelancing, but at the same time I was like, Well, if there's any place that going full-time would probably be close to freelancing, it would probably be Upwork. So so what I ended up doing is taking a week to do an audit of the, the team and the brand and basically telling her like, Hey, this is, this is what I really think the, the cre like the role creativity should play in this organization.

And it was basically shifting the organization from being what was, you know, basically like a, a short order cook situation. Just, just like, Hey, you need this banner. We'll make you this banner and this amount of time to being more of a strategic and conceptual partner to the larger organization, both the, the marketing organization, but then like the, the, the company in general. And I put together this, this deck, and it basically was like more head count, complete change of, of what the team does. All all the things that are very scary typically to leadership of organizations like these paradigm shifts fully intended them to say no. Like literally, I, I almost kind of like tried to go a little bit far in certain places, so they'd be like, like, force my own hand so I wouldn't have to take a full time job.

But to their credit you know, it's human man's credit. She was like, No, this is exactly what we should be doing. And I was like, Fuck yes, let's do it then. And so that's what I've, I've been spending the past 18 months doing alongside my team. Now we, we run just like an agency, we're actually branding ourselves like an agency, which seems like every in-house shop is doing right now. But I think it is important because, you know, you are dealing with clients, you are dealing with stakeholders, you are dealing with, you know, deliverables, all these kind of things that agencies do. And most people, if not every single one of them on my team came from agencies. So that's what we've created. We've you know spent a lot of time in blood, sweat and tears and all that kind of stuff doing that. And now we have a, a team of about 40 people and 80% of them are freelancers. Many from the Upwork platform. We reside all throughout the country and the world, and they are, without a doubt, the best people I've ever worked with.

Nate Watkin: Yeah, I think that's, that's fascinating and makes total sense that 80% of the team is freelance. And this goes to, you know, something that you talk a lot about is that you're really fighting this battle of in-house versus outsourced, right? And, and this comes through in the new brand campaign and everything which is something, you know, our company, we focus on collaboration software, remote teams, specifically in the creative fields and a lot in production. So this is our belief as well, Like the world is moving towards a more remote model where workers have, are, are more empowered to pick and choose what they wanna work on and live the way that they wanna live and, and just work the way that they wanna work. But I'm curious to hear your take on that and tell me more about where you think that balance is headed, is outsourced, the future, What does that look like, in your opinion?

Patrick Holly: By outsourced, do you mean like using outside agencies or outsourced? Do you mean like using freelancers?

Nate Watkin: Just the difference between full-time in-house versus any sort of outsource, whether that's freelancers, agencies just that, that mix.

Patrick Holly: Great, great question. So I think we're at an inflection point in many ways right now. The first one is one that I've kind of been observing for a long time in kind of as someone who's, who's ping pong between brand and brand and agency for his whole career, is that some really, really great creative minds over the past 10 years or so have been moving from the upper echelons of the agency world into leadership roles at brands that has created a world in which your in-house team can be, you know, just as powerful as an agency. And you don't have to bring in agencies to like, make the fun stuff. You bring an agency to augment your team because you don't have, you know, enough head count this very moment, or you don't have knowledge in a specific sector or whatever. But it shouldn't be like a you know, you can't find great creatives to work internally at your team because great creatives don't wanna work internally.

I think that's completely changed now. So like we've got you know, amazing amazing people on our team who have come from places like you know, leadership positions like, like group creative directors at Media Arts Lab, or widening Kennedy, like creative directors. All these people who you know, any, any brand would be lucky to get when they're hiring, you know, that agency now, you know, if you are willing to create an environment that is conducive to them making great work, are willing to work for you. And I have recently become friends with, with David Lee from the CCO of Squarespace. And he had an illustrious career in the, the world's biggest agencies before he went over Brandside. And over the past 10 years at Squarespace, he has built a team of, I think it's about 75, that are, they make everything in house when a hundred percent of everything they make from banners to super Super Bowl commercials is in house.

And so it absolutely can be done. It just takes time to earn the trust of creatives and to be putting out that work that that attracts them. Like, for example, our new campaign, when we did it, I had like hundreds of, of messages in my LinkedIn being like, Hey, are y'all hiring? And it was people from like, Droga five, and why didn't people like you'd, you'd really want to have on. So I think like, first off, you can build an amazing internal team but second, doing it without thinking that freelance should be a main pillar in which you, you know you run that team is setting yourself up for failure. Because a benefit of agency running the agency model is that you can fire them if one, they're not good, or if cost hap cost cutting happens.

Cause agencies are very expensive. And so if you can bring on, you know, amazing freelance talent based on needs, you're able to scale up, scale down, do whatever you need to do and be a nimble internal shop. And so that's why 80% of my team are free freelancers. And it doesn't mean that they're necessarily on the team for just, you know, a couple of days or, or, or even weeks or months. We have people on the team who have been freelancing for us for four years, but it does allow for them to have the freedom to work the way that works for them. You know, some people on our team, like, there's one person who's, who's on a strategy team, Alana, who she works a bit of a hybrid schedule because she runs a farm with her husband. And so like they're able to have these kind of these kind of ways they, they could basically work the way that works for them to put it simply. And it also allows for brands and people like myself who are running them to properly staff up, scale up when necessary, but also be able to have a, a dynamic model that allows for us to adapt to you know, the shifting <laugh> tides of, of business. So, I mean, I'm never going to build another team that is not in this way ever again,

Nate Watkin: You know, you, you allude to this a lot is the Hollywood model, and it's something, you know, my background is in the film industry and as you know, in the film industry, it's this this industry of highly, highly skilled professional creatives that come together one project at a time, you know such as a Hollywood film, Create that project, create something amazing, and then really disperse and potentially never work together again. What's interesting, I think, is that Hollywood Studios, in my opinion, were like the first big creative companies, right? Like they, and when they launched, they initially had all those creatives on staff, the directors were on staff, the dps, everyone was on staff, and they just turned out movies. And eventually that model dispersed and everybody became more freelancers. And then you had the agencies come along like the next big creative companies. And I think we've seen that similar trend happen with the agencies becoming more every, not everyone, but a lot of people becoming more this freelance model. And I, I feel like as we are moving towards more and more knowledge workers and companies just being creative companies in general, this trend maybe continues to happen for all companies. I mean, do you, do you see everybody following that Hollywood model in in the long term?

Patrick Holly: You know, it's funny you bring up the Hollywood model that that was the first time I spoke at Adobe Max last year. That was like the, the theme of it. But the, the most recent time this past literally actually a week ago today I was doing a talk there and it was all about kind of like how you can build culture and trust with your workers. And one of the slides was outputs over inputs. And it was basically like, you know, the old way of working was making sure that someone came into an office, sat their butt in a chair for eight hours, had you know, their coffee break and sat their butt back down and then left at five o'clock. And it's like that whole model had nothing to do with what that person was actually doing and the value that they were providing for themselves and for the company.

And so, kind of like this new way of working is trending more towards an outputs over inputs kind of model. One that is like, Hey, I'm hiring you Nathan to make this thing for me, or to provide this service for me and my team. The amount of time you do it in is, is almost kind of, doesn't make a difference to me, but the, the, the quality of that output is, is the most consequential thing. And I, I had a line in there where I said unless you're hiring security guards, the number of hours someone puts in is completely un inconsequential. So if you are hiring these knowledge workers, you are going to be able to find a much more economical way of building teams and making great work if you embrace this kind of freelance first model. And when I say economical, I don't just mean like, Oh, cost savings and stuff.

Sure, yeah, absolutely, you can save costs, but I mean, like economies of of time, economies of scale it allows you to, you know, have somebody who's, who's motivated by, by providing value as opposed to providing hours on a time sheet. And it also allows you to, you know, provide those economies of scale where your company can scale up like that. If you're used to bringing on freelancers and molding them into your team and, and you are working with people like, you know, the folks on Upwork, shameless plug that have experience working freelance before and, and come kind of batteries included like that then you're gonna be able to scale up quickly. So it, it kind of like more economical way of working sounds really devoid of all emotion and pretty dead, but hopefully it, it kind of has that, that depth and nuance that I just tried to explain.

Nate Watkin: Yeah, no, that, that's super interesting. And it, it mirrors a conversation I had with another guest Joel Pilger, who's a, a consultant to creative, creative firms. And he's trying to, you know, one of his goals is to kill the line item bid. If you're a creative company and you're bidding on work and just, you know, rather than clocking the hours a as you say, and putting together a bid, this is how much each hour costs of our work they're, they're not buying that, they're buying the output, right? Like they're buying the, the final delivery, your creative talent what, what's in your portfolio. And it sounds like that's kind of a shift that you all believe in Upwork as well. And it's really just like shifting to a more economy of trust, right? Like the old model is, yeah, if you're not here sitting in this seat and I can't see you working every hour of the day, then I'm not getting my money's worth. Versus this new model, which has been driven a lot by remote work

Patrick Holly: That is super well put. And I'm definitely stealing economy of trust. That's amazing. <Laugh>. Yes. Like 100%. And, and that's like you know, I also had another slide in my presentation that just said, work is not adult daycare. Like work is, is when people come together to make something that is greater than some of its parts, it's not somebody looking over your shoulder and saying, Nathan, did you put in your eight hours today? You know, that's not, no one actually wants to work like that. That seems almost dystopian just the way that I said that. And so, you know, we want to, you know, encourage this world that is where work rises to our potential, not the other way around, you know, And, and where, where people can find, you know, growth and fulfillment and, and value both in what they can give to people, but also what they're giving to themselves in the way that they work, work. Cuz if you have that trust, that unlocks all the rest of that

Nate Watkin: A hundred percent. And yeah, economy of trust, it's all yours. As long as I see it on a billboard next time I'm in New York, <laugh> <laugh>. And so, circling back to your team specifically, and, and how you're running this, I mean, 80% freelance really in incredible, a lot of people talk about how do you build a culture with remote work. But I think when people say that they're mostly thinking about a former full-time team that's now working remotely, I think it takes it to another level when you're not only working remotely, but it's a large percentage of your team as freelancers that may be coming in and out. How do you think about maintaining culture in that scenario?

Patrick Holly: That is the most important thing to me and to my leaders, is like, how are we going to make sure that we create and maintain and grow a culture in a world that is the remote world, that is, you know, so counter to that, at least on its face. You know, when we first went remote building culture in that world was the equivalent of like, zoom happy hours, and these kind of like weird things that we're like, Oh, the stuff that we used to do, but just now it's on camera and we're apart and just, it rings hollow. I dunno if you've ever done zoom happy hour, but yeah, yeah, they fucking suck <laugh>. And, and the reason why, it's because we're trying to take something that was in person and thinking that it has the same effect when you're not in person.

And the reality of that is that it's just, it's not the same going to see a a football game, for example, in person versus on TV or two completely different experiences. But they look similar. But when you actually come down to, like, you have completely different feeling towards one or the other. And so what my team and myself try to do is to look at all the things that we used to do to build culture, distill them down to why they were actually good or in some cases bad, and then adapt new ways of, of building said culture by mapping them back to those values. And so what we ended up doing at the beginning of this year was to create a set of team values that was based on, on, on just that, on kinda like the things that really we believe in that, that made our cultures in the past.

Great. And it's, it's five things. It's kindness craft communication, drive and humility. And, you know, some of those speak directly to like, you know, you can clearly understand that they're like, let's make great work kind of things like craft and drive but all the rest of those are have nothing to do, at least on their face with like, making creative work. But when you kind of dig a little deeper, they, they have everything to do with maintaining an environment in which creative work can be made. And so you know, we spent a lot of time figuring out what those, those those values are, but then it also allowed us to kind of like start doing things that allowed for us to build that culture. I'll give you a couple examples and then then I'll shut up.

But the kindness is the first on our list for a very important reason. And it followed closely by communication because in this new world where we see people as boxes on a screen, it's really hard in some cases to remember them as people, you know. And so we always try to create space and time for treating people like people and having human conversations because you know, right next to you, your face right now on my computer screen is my calendar for the week, and it's just meetings and, you know, what do you do in meetings? You talk about work. And when you only talk about work with somebody, it's just, you see them as that just an interface with which you work with as opposed to a person that you work alongside. And so with my team, whenever we meet, for example, during our, our our Monday kind of team syncs we don't we don't spend a lot of time talking about work.

We start off by having a competition about who had the best weekend, which is always fun. And then as we give each of the updates throughout the team, like each of the director starts talking about, okay, these are the top three things that we're thinking about right now. Before we even get into that, someone shares something. And like, for example, Todd Lamb, who's a creative director of copy on our team every week he does a, a Trader Joe's snack review. And he's now branched outside of Trader Joe's. This, this week it was Oreo Cakesters. And he had a very rare one star review of Oreo Cakesters, usually his, he's got, he's got some pretty, pretty favorable reviews of his snacks. But, you know sl line B who is the head of our, of our ops side of the house, she does like a a horoscope reading for people.

Like, it's, it's us talking about things very deliberately talk about things that are not work, because that's all we usually do. And, and that's all we will do if we let that happen. And so these kind of moments to, to talk with each other is important. And, and so when it comes to, to communication and kind of stuff like that, like we really try to, to kind of hammer those down. And that, that actually comes to the most important thing, I think, which is the last thing that we do on our, our our our Monday meetings, which is a moment to give thanks for each other. So we spend 15 minutes at the end of, of our, of our sync shouting people out, being like, you know, Hey Nathan, thank you so much for, you know your work on you know, the brand campaign this past week.

I know it's been really tough. You've made my life way easier and you know, I can't thank you enough for, for everything you do. You're a rockstar, Appreciate you, you, And then that just kind of goes on for 15 minutes. People just give thanks for each other. And it's, it's it's nice because it's nice to get a compliment, but it's also nice because in this world where we are just kind of like it can get very transactional if we let it when you have to have a tough conversation with somebody, cuz a great culture is made on, on, on well trodden paths of communication and, and the ability to have tough conversations if need be. You know, we wanna make sure that when those tough conversations need to happen, it's not the first time you're talking with that person as a person. You know? If you only had seen that person in large group settings and they were just a box on a screen, maybe even video off, you know, you don't have that person to person connection. You don't feel that empathy, you don't feel, you don't see that person as, as as a reflection of yourself. And that is, we try to take as many opportunities to create those humanizing moments as possible. And they seem silly and they seem trivial, but I promise you they're not.

Nate Watkin: No, that's incredible advice and, and that really resonates with me. I mean, I think that is the difference between looking forward to that meeting, right? Like people, I, I assume on your team probably have good emotions around that meeting because it's about personal connection. It's not just another zoom call on the books. And I think that's probably what we're missing a lot of not going into the office is those just seeing your friends, right? And hanging out with your friends at work. So that, you know, that, that makes so much sense to me. Definitely, definitely resonates. I wanted to talk real quick about your new brand campaign. I don't mean real quick because it, it's amazing and I want to, I wanna dive in here, but so you worked with Alto agency to create the, this is How We Work Now campaign, and this really got pretty fun. I mean, a year ago looking at the ads, they were, they were super well done, very cinematic you know, very, very nice ads. And then this year really flipped it on its head. You've got this CEO zombie breaking into like Broadway musical song and dance. <Laugh>, we'd love to just hear the process of how that went, especially like getting that approved internally and how a company like Upwork was open to such a out of the box idea.

Patrick Holly: So first off, huge shout out to Alto Honas and Ed and, and Shannon and Jason and Jeff and, and Brock there, like, honestly and Ashley, they're fucking amazing creatives. Like they're some of the best people I've ever, I've ever had the, the pleasure of working with. And and they actually did, they did that campaign for us before that, that last one you were referring to too, like the one before the zombie one. You look at those two campaigns and they, you know, as the British say, they're chalk and cheese, like they couldn't be more different, right? And the reason why that paradigm shift happens is complicated and simple at the same time. It was complicated to get there, but it was simple in terms of what we did to get there. And so it started with, with Melissa Waters coming in our, our CMO and she is a a wonk for strategy, which I love because so am I.

And she was basically like, Hey, we need to kind of like take a, take a step back. We need to think about who the hell we are as a brand. We need to think about what we're making and why that is going to be successful in terms of differentiating us from the rest of the opportunities that people have to connect with, you know, the fibers and LinkedIns and literally anything else in the world to find people. I mean we need to do so in a way that is, that is ownable by us not only just for this campaign, but for the long term. And so what we ended up doing is embarking on a multi-month kind of like vision quest where we were thinking about like, who the hell are we, what are we trying to provide to the world? How are we gonna stand out?

And we got a lot of strategic kind of rigor out of that and a lot of great work. But in terms of like how it actually impacted this campaign and got us to a talking zombie is that we took a look at, at the rest of the the, the competitive space within staffing and it is really dry, it's overly earnest. And so what we wanted to do was be the opposite of that, you know, And, and not to take anything away from our, our previous campaign cuz like you said, it was cinematic, it was beautiful, all that kind of stuff, but it was very earnest, it was serious, it was, you know reflective of the moment we were in to be fair. But we're, we're now kind of coming out of that moment and we're, we're looking to to, to zig when everyone else is zagging.

And, and that took the turn, took the the form of, of Jack McDill, the singing CEO who comes back from the dead to tell you that the ways that you've been hiring have been wrong all along <laugh>. And so we were lucky enough to have a fantastic creative team internally and a fantastic creative team over at Alto that worked together to, to come up with this stuff. And and it was the core creative team over there working day to day on this was was Jason Bagley who did all the Old Spice stuff at Liden. He was an ECD over there. And then the, the, the team was was Brock Kirby writer and and, and Jeff Dreyer as an art director. And, and they've, you know, done countless iconic, very funny campaigns before. And so, like from a, from a creative standpoint, we were like, it's on us to fuck this up <laugh>. And luckily we, we didn't and we have a fantastic campaign that, that is now running on a television near you called, This is How We Work Now.

Nate Watkin: I love it. It's so well done, so hard to pull off comedy, but it seems like the, you, you had an amazing team there from top to bottom.

Patrick Holly: Yeah.

Nate Watkin: And who, who are you marketing towards? I'm curious, like are you, are you going for the enterprise? Is it the solopreneur? Like who who are you speaking to?

Patrick Holly: It's a great question and it's a very complicated one to answer. And the reason why it's complicated is because we're kind of going for everybody, but for different reasons. So when you think about, like, when you go back to what I was saying before about like the well and like how deep a, a brand story is and how Upwork is the deepest one I've ever seen it's because literally everybody in the world has a story around work and experience around work, and almost all of them do work. And so we as a company are trying to create this paradigm shift in the way that we all work into kind of this glorious, you know future. We're really glorious now in which you can have you know, all the talent in the world and that's it, <laugh>. And so we, we target directly kind of like our, our clients, if you will.

So like any of our marketplace, we've got two sides buyers and sellers, we call them talent and clients. And so we, we end up targeting the the clients because they're easier to target, you know, there's fewer of them. Their motivations are are pretty solidly understood, but also because they are you know, they are the drivers of, of commerce, they are, if we want to really change the way that that we work starting with them is a really good first step. So we do a lot of you know, direct targeting to them, but we never do it without making sure to do it in a way that heroes talent, the hero's the worker that shows, you know the, the, the client, Hey, you should work in this, this way. And the reason why is because great talent is freelancing right now and they want to work this way. So if you want to keep succeeding in the future, get on board, we'll show you how to do it.

Nate Watkin: Hmm. Yeah, and I could, I could talk with you about this stuff forever. I mean, this is really what I live and breathe, but unfortunately I know we're almost at time, so I, I wanna leave with this last question. What is your vision of the future of work look like 50 years from now? I mean, is it, is it a DAO, is it a, a fully decentralized you know, system that gets rid of the hierarchy and is just based on contributions and votes? Or is it some hybrid of where we, we are now? Would love to know what what you think that future looks like?

Patrick Holly: That is I, I barely know what a DAO is. I know enough to have a conversation drunkenly at a, like an Austin tech meetup, but that's about it. But I, I will, I will give you kind of like my honest opinion on, on, on what I think the future will be and, and or what I, what I want it to be. And it's, I, I want it to be free. I want people to have the freedom to make the choices that, that fulfill them, and that allow them to work the way that works for them and allow us as a, as individuals, but also as a culture to see work as as a means of growth most professionally, of course, but like personally and, and a place in which people can, can be connected to, to opportunity no matter where they are.

I want, like the same way that I grew up at a place where it's like, there's basically like two choices of what you were gonna be when you grew up. Like I want everybody throughout the world to have a million choices and to have examples of people who have succeeded in those and coaching and, and means of finding that work. Like Upwork, again, shameless plug, but for real, I think like that's the reason why I'm excited about working here is cause I think like this is, this is the future. Like having, having a, a place where people can go and, and sell their wears you know, meaning their kind of, their, their intellectual you know, gifts and, and being able to do it in a way that that feels equitable and, and serves not just the person who is paying for that work, but the person being paid for it too and, and serving them more than just in, in the monetary sense.

Nate Watkin: Yeah. Yeah, absolutely. It's, it's an exciting future and I think we're gonna see a lot of change in these coming decades. But thank you so much for joining us. Really enjoyed the conversation.

Patrick Holly: Thank you, Nate. Really appreciate it.

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