Hiring & Managing a Distributed Workforce

Chris WinnCTO

CreativeMarket CTO Chris Winn explains how their company has grown to be comprised of 2/3rds remote workers, as well as how to hire them and train hiring managers to best lead them.

Episode Transcript

00:00 Rob Stevenson: Hello podcast land or at least hello to the small stretch of podcast land concerned with talent acquisition. The recruiter is Miss Tucked away in a corner of podcast land and sprawling out over a glistening podcast land Bay. Welcome back to your favorite recruiting show, and thank you for choosing us over my favorite murderer, or Invisibilia or Shaq’s podcast. Did you know Shaq has a podcast? . I don’t recommend it, but it’s out there man.

00:28 RS: Anyway I’m Rob Stevenson here surging more sweet recruiting content into space and time, from the cozy confines of Hired HQ. If this is your first time joining us, here’s the skinny, every week I’m going to be bringing in my favorite people in the recruitment space, Directors of recruitment, Heads of talent, VPs of HR, you name it, I’ll get them in here and there we’re going to do primarily one thing, “Talk Talent To Me”.

00:52 RS: And today I have a banger of an episode lined up for you. Did you know that the future of work is a distributed remote workforce? . This is not a theory, this is a fact I just thought of. No it’s true, people aren’t so sure anymore about going into the three-dimensional world in order to earn living, and as it turns out this works out great for hiring teams because it provides you a bunch of advantages over hiring solely around your office. What are they Rob? I’m not going to tell you, but my guest today, the CTO of Creative Market Chris Winn will. Because Creative Market boasts a two-thirds distributed workforce and Chris has seen first hand the advantages of having remote teams.

01:32 RS: He told me all about why you should have a remote workforce, how you should train hiring managers to lead them, what to look for when hiring people who will primarily be remote. This is a really interesting episode about a company with a unique hiring strategy which has allowed them to accomplish some really great things. I’m really excited for all of you to hear it. So without further dithery dottery I give you Creative Market CTO Chris Winn.


02:38 RS: Chris, welcome in, how are you this morning? .

02:39 Chris Winn: Yeah, thanks for having me.

02:40 RS: Yeah really glad you’re here, you’re on the heels of your second baby, congratulations.

02:45 CW: Thank you, thank you.

02:45 RS: So that was relatively recently, now you’re kind of just back in action, right? .

02:49 CW: Yeah, so I took a few weeks and did the new baby stuff, but this is our second so we’re… We think we have a handle on this.

02:56 RS: Right, right. It’s a little easier around two.

02:58 CW: Yeah.

02:58 RS: Well, there’s a incy wincy hired onecy, [laughter] [03:03] ____ in the office so we, [03:04] ____ we had made for you, so I’ll make sure that we get that in your hands.

03:06 CW: Thank you.

03:06 RS: But yeah, you’re back in the office, was your inbox an unmitigated disaster? .

03:12 CW: I will be honest, I did not completely leave during paternity leaves. I was keeping up with things, but had a good still felt like I had a good balance, so I got back and got caught up pretty quickly.

03:25 RS: Got it. I really wanted to ask you all about the remote hiring that you’ve done over at Creative Market, because it seems like it’s a pretty big part of the recruiting and hiring plan right? .

03:37 CW: Yeah, we are a distributed company with an office in San Francisco, that’s how we think of ourselves.

03:42 RS: Okay, so the home base is here, but you are primarily out of whatever you can get people.

03:49 CW: Yeah, so we’re primarily out of six states and that’s to keep, keep things a little bit simpler. So we hire in California, Texas, Washington State, Colorado, North Carolina, New York and we’ve got about a third of the company here in California, out of our San Francisco office or nearby, but we also, we’ve got a bunch of people in Texas, Seattle, all over the country.

04:13 RS: Was that always a part of the life blood of the company, or was there a certain point where you decided that it would make more sense to hire this way? .

04:20 CW: So we started remote, I’ve been at Creative Market for about five years and even when the company was founded, the founders were on different coast, different places. We had our first…, one of our first offices was in Potrero Hill, was a little closet of a space just a few of us, after YC, but now for the most part we were always remote. I joined remote, I was actually on the East Coast when I joined Creative Market, so it was always a part of our DNA mostly because we were small and scrappy and trying to get, you know just get set up, but over time when you’ve got people that are remote, and that becomes part of your culture, you stop and take a breath and think about it and try to be a little bit more intentional about supporting it the right way. So now we…, I think we do look at it as a real part of our culture and important part of our culture.

05:14 RS: Yeah, of course. How do you make sure that these people feel part of the team if they don’t have the colleagues if they’re not going into a place where they can make avocado toast on the English Muffin.

05:26 CW: Yeah, no it’s a great question, and it’s something that I also think can get lost really easily. If, for example, if your leadership team or your managers are centralized in a particular area say San Francisco, but the rest of your team is out there in the country, it’s hard even to have empathy for what that’s like, what does it mean if you can’t serendipitously have a moment in person one day or it’s hard to have their world view from their perspective and so one of the advantages that Creative Market has is our hiring managers, our leadership team, we are distributed too. We’ve got a few people from the exec team, and our CEO in San Francisco, but me, for example, I’m in Boise, right now, and we have another member of the exec team that’s in Austin. And so, and even in my group, my engineering managers, they’re in Texas, and they have direct report to our remote. And so, having that empathy and that world view, it helps you support those people. So one really simple example, one thing that’s really important is when you’ve got a new hire, still bringing them into the office, bringing the team together physically because a lot of times those really early moments that are in-person enable a lot of the online conversations later.

06:56 CW: I remember talking to someone on our team, getting feedback about what it’s like to be remote, just kinda checking in with her, and one of the things that she said was really interesting to me was that, we had just had a team trip, and she met an engineer on our web ops team and she’s an SEO Manager. So those paths don’t always cross, as often, but because they had had an in-person conversation in our office, they ended up having some really interesting conversations over Slack a few weeks later. Even though they’re in, she’s in the Seattle are, he’s in Portland area. And so, as much as we’re talking about being remote, some of that in-person collaboration is really important for forming relationships. That’s important, making sure that you have a hiring process, a promotions process, all of that, making sure that it’s sort of equitable in terms of location, and that people are getting the right kinds of opportunities, and are getting elevated, and rewarded, so that they’re not feeling like, “Hey, I’m on an island and I don’t have the same opportunities.” That’s an important thing too.

08:05 RS: Right. Are there processes you put in place to measure and make sure that people are being treated in an equitable manner?

08:11 CW: Yeah so, one really simple thing is setting up hiring managers to understand what it means to manage remote people. So, I was kinda forced into it because when I joined the company, I was remote and my direct reports, they were remote. And I don’t think I ever thought about the things I was doing, because it was just coming naturally, but reflecting back on it now, making sure you’re reaching out to people a lot, and connecting with people, making sure that you, as a manager, that you’re setting people up to be able to give feedback the right way, and to have those one-on-ones, and all the tooling and things that go in place too, like the video and Zoom rooms or whatever you’re using, right, hang outs, whatever. Making sure that those processes are even, so I don’t give someone that’s in person, if I’m in the San Francisco office, and I’m here every few weeks, I don’t give that person feedback any differently than I would someone else, or we have a 360 program at Creative Market, everyone gets the same 360. And honestly, at the end of the day, the other thing that’s interesting is that, even if you’re in the office and in San Francisco, at the end of the day, everyone is remote to everyone else. Everyone’s distributed, the people that are in the San Francisco office, they’re distributed. If you’re looking at them from Texas, right? And so it does have to work kinda evenly everywhere.

09:39 RS: Yeah, definitely. Would you say that this hiring approach has been a competitive advantage for you in terms of capturing talent?

09:46 CW: Yes, a hundred percent. There’s so many smart people in San Francisco, there’s smart people all over the place.

09:53 RS: Turns out, yeah. [laughter]

09:54 CW: Yeah, there’s lots of smart people in the world and hiring goes faster and we get to focus on just finding the very best talent, wherever you are, within reason. We do care a lot about time zone overlap, and meeting overlap, and things like that. ‘Cause we are really a collaborative team, at the end of the day. But yeah, we’ve been able to hire so much faster because we’ve got that flexibility.

10:19 RS: Are you able to find people who are already more amenable for remote work, or how do you… I’m thinking about the sourcing stage, ’cause even if they really love Creative Market, and they thought it was a great opportunity, you would have to say, “We want you to quit your job and stop going to an office and we’ll help you set up your home office, and then now you work at home.”

10:40 CW: It can play both ways. So one way is that, there are a lot of people that are looking for that flexibility. We have people on our team that, it’s not ultimately why they chose Creative Market, they chose Creative Market because they’re really excited about what we’re doing and our mission and our product, but they got interested because we allow remote work. That was the hook, at the very beginning. “Oh, I don’t have this flexibility and I’m kind of looking for that flexibility.” “I’ve got a tough commute.” Or, frankly, they’re just not with a team that they love, maybe, and they’re not feeling that same connection that you do get when you’re in the office. And so that sometimes the hook. The flip side of that, though, is there’s also a lot of people who have had a really bad experience working remote ’cause it’s not great everywhere. And so, one of the things that’s important in our hiring process is, we hiring managers, we really have to know how to pitch the value of it, and that really to prove and to earn their trust that we know how to do this. We’ve been doing it for a long time, it’s not our first time hiring remote and having a distributed team. And if they saw some things in the past that maybe were a little funky or didn’t feel great, we’re way past that, we’re just so ahead of this because we’ve been doing it since the company was started.

12:00 CW: Right, right. And that’s not so different, at least in the early stages, from any kind of phone screen a recruiter would conduct, right? They’re assessing for candidate motivations, they’re trying to learn why they might not be a hundred percent satisfied in their current role, what they’d be looking for in a new one. I guess you could, even in the event that someone had remote PTSD, you could connect them with one of your other remote workers. And like, “Here, straight from the horse’s mouth.” We are really intentional about the hiring panels in a lot of different ways. Obviously, diversity and inclusion, but also, diversity can mean a lot of things. And one of the things that we put into our hiring panels is, where are you from, what does work look like for you? So for example, if we’re hiring… Say we find someone that will be in our San Francisco office, on that hiring panel, we really want someone, both that you’re gonna be sitting next to and working with every day, we also want someone remote ’cause we wanna make sure that the relationship is gonna work both ways, and so we even… We even bake it into our hiring process from that perspective. We also screen for certain things.

13:02 CW: A lot of it’s about setting expectations. Do you have a quiet place to work? Do you have fast internet? Are you set up for success in your home environment? Because, ideally, you’ve done this before, that’s the best. If you’ve got experience working remotely. And I did, before I joined Creative Market, it was my whole career, was working remotely. But if you don’t, we know how to set it up the right way, but if you don’t have a quiet work environment, it’s tough to get work done. That’s true whether you’re in an office or not. And so we wanna make sure that we’re screening all of those things before the offer letter even gets out [13:39] ____.

13:40 RS: So probably should have done this at the top of the hour, but I’m bad at this. The benefits of remote hiring, I guess we skated it across a little bit of it, competitive advantage because you can hire anywhere, you’re not just operating in your own talent market where you might have an office. Presumably, if you’re hiring outside of major metropolitan areas, it’s a little more affordable, cost of living is lower in more rural areas, even though the talent might be just as good, what if someones riffing, what are some other advantages?

14:10 CW: Another advantage to is that, if you do it intentionally your whole team is distributed versus what I see sometimes with companies is they, really do wanna hire for that office or that one location, but every so often they get some stragglers they have some remote people and what breaks about that over time I feel is, if you’re not going to just make the investment and think about making it work every day, those people do feel isolated.

14:38 RS: Right.

14:38 CW: ‘Cause there’s little things along the way that happen in their experience at the company, and they don’t feel as connected. And so one, it sounds silly, but one advantage that we have too is that, we do it, and we think about it, and we care about it every day.

14:57 RS: So this has arisen throughout, grown through the culture of Creative Market. If you don’t maybe have a sincere investment in remote at your company, what does the project look like to make that apart of the hiring process, I realize that’s a little unfair to ask because you didn’t have to throw it into a large developed company, but I just imagine it would probably have to come from talent. Meeting with people like yourself, with hiring managers, coaching them for empathy, retraining and sourcing a little bit. How do source for people who are going to be good, remote workers?

15:39 CW: It’s tough and yeah, I haven’t done this with an existing company of having to bolt it on later, but as I think about it, it’s a big project. It’s tough to install it later. I would imagine at some companies the temptation is to do it with a new team. So say, it’s the company that adds the sales team later, and there sometimes is a different culture or there can be, within a company. It’s tough to bolt it on later. It’s tough, especially again, because those managers and the leadership team, they’re probably already there in that one location.

16:26 RS: Right.

16:27 CW: So, they miss out on the empathy. And I would say you really have to at every step of the way, think about, how do we wanna solve this, if we’re going to invest and distribute it, what needs to change with this specific thing? So, I need to talk to my recruiters, I need to recalibrate, I need to open up this market, I need to understand what happens to our hiring process, I need to talk to my managers, I need my hiring managers to be able to pitch…

16:56 RS: Right.

16:56 CW: And say why this is great, and why we’re gonna make it work. And also I would say if you’re running a company, also let yourself off the hook a little bit, because it’s a really big change and you’re probably not going to read… I just wrote a medium post about this.

17:12 RS: Yeah.

17:12 CW: You’re not gonna read my medium post and get it…

17:15 RS: Maybe you should, but.

17:16 CW: Well read it.

17:17 RS: Your point is that, yeah, you might not nail it on the first go.

17:19 CW: You’re not gonna nail it, and that’s okay. The important thing is that you care about it, and you’re investing in it intentionally and thinking a lot about it, and then you’ll get good at it over time, it’s a muscle to flex.

17:29 RS: Totally.

17:29 CW: It really is.

17:30 RS: Definitely. What then is your ideal relationship with the recruiting team, in light of so many these higher being remote?

17:36 CW: The thing that I want the recruiters to do is to pitch the value the same way I would. I want… Again, it’s good if our distributed culture and team is the hook that gets you in the door, that’s okay, but I still want you to be really excited about Creative Market and the product, and why we do what we do, and that you’re gonna come to work everyday and make this company better. And so, that’s the thing I think a lot about is that really careful balance between, “Why are you really excited about this?” If it’s only the remote stuff. That’s not enough. That’s not enough for us.

18:15 RS: Right, right. Yeah.

18:17 CW: So we have that conversation with our recruiters and make sure that they’re pitching the value. We also, if they do have that distributed or remote PTSD. We want to at least get on the phone with them. And really… Because I can get on the phone with someone and I can, and genuinely, not pitching in a dishonest way, I can genuinely convince just about anyone that we really are good at this.

18:43 RS: Right.

18:43 CW: We’ve done it. I experience it. I sit on our exec team. I’m the CTO. I’m remote.

18:52 RS: Yeah.

18:52 CW: And I love it.

18:53 RS: Yeah.

18:53 CW: It’s great, and I’m a people person, too. I love meeting in person with our team. I’ve come into San Francisco every few weeks, so I get both sides of the coin, but we really are good at it and getting the opportunity to make that pitch if they do have that experience in their background, of… “Oh, yeah I don’t know about this. I’ve been here before, I don’t like it.” No, it’s okay, you can do it the right way.

19:16 RS: Right, right, so then you would want the recruiters to suss that out?

19:21 CW: Yeah, I think it’s important to have a little bit of that context going in, and to know…

19:27 RS: Where you wanna approach from because again, some people, they do have that bad experience, and some people are really, really excited about it. And then you wanna swim the other way and make sure that you’re vetting for… Are you really excited about this company and this product?

19:43 RS: Right.

19:43 CW: Not that…

19:43 RS: To work in pajamas.

19:45 CW: Exactly.

19:46 RS: Merely to work in pajamas, yeah.

19:47 CW: Which I also don’t recommend if you’re a remote worker…

19:50 RS: Yeah.

19:50 CW: It’s all about habit.

19:51 RS: I agree, I’ve been working remote and the first month was a little sloppy, and then I was like, “You know what, I’m gonna get up, I’m going to get dressed, I’m gonna act like I’m going to be… Participate in the world today.”

20:01 CW: Yes, when I started my career, I was remote from day one of my professional career. And I have had my alarm set at the same time for 15 years, because it’s… You really do, you need that habit. Every day, you gotta have… People say, some people say that working remote is easier…

20:29 RS: It’s different.

20:30 CW: It’s different, and it’s not always easier, sometimes it’s a lot harder ’cause you have to have your process for being really successful.

20:37 RS: Right, and the self-discipline that goes along with that.

20:40 CW: Yes, yes.

20:40 RS: Is your recruitment team distributed?

20:42 CW: Yeah, yeah. So we’ve got a team in different places focus on different markets and then hiring managers inside the company are all over the place, not just in San Francisco.

20:56 RS: Okay, how does that work?

20:58 CW: In terms of?

21:00 RS: So I guess that… Not a fair question, is it different department to department because there’s some… Like engineering they prefer to be in… Work in silos at times, right, in a distraction-free, turn off slack, for example. There’s an engineer here at Hired, who he has fashioned out of cardboard, these triangular horse-blinders that he leaves on to his glasses so that he’s getting no periphery distraction.

21:25 CW: To each their own.

21:26 RS: Right. Yeah, fair enough, if that’s what he needs to be productive. But so recruitment or sales, these are, this is a more people first sort of function, does it, does the remote work differ department to department?

21:38 CW: Yeah. That’s a great question. In short, no. So we’re distributed everywhere, and we really try to make sure that even at the department level, people are really engaged in making this successful, because silos are not necessarily a bad thing. If you’re in a growing company, silos can be really great, you get a lot of work done. But you cannot be siloed in your culture and you… And so what I mean by that is, even when we are working cross-functionally, and we have say a product squad, we try to be really intentional even about how that squad is distributed. Is this product team all in San Francisco, are they all not in San Francisco? Where is the product manager, where are the engineers, where are the designers? It’s not a perfect science, all the time, especially, because sometimes people move around or whatever, but we try to make sure that the company is distributed as best we can in every department, every function, everywhere. Design, that creative market is distributed. Ironically, we actually really wanna find someone in San Francisco because design is not in San Francisco so much.

22:50 RS: Right.

22:51 CW: Engineering is mostly not in San Francisco, but we’ve got a few engineers in San Francisco. And yeah, so it really, it varies a lot.

23:03 RS: I’m trying to put myself in the shoes of a recruiter, who is working in this kind of team. Maybe it’s not fair to ask you about the in the weeds sourcing, sourcing part of it, but I’m sure you’ve had role kick-offs and a standard sort of meetings, [23:20] ____ conversations you have when you open a new role that you would have, as a hiring manager with a recruiter. Is there some kind of re-skilling necessary on the part of the recruiter, to source in lots of different places? Are they still sourcing locationally, because it seems like people are still clustered and when you go out to find people, what kind of search would lead you to find people that are all over the place, as opposed to in one city?

23:44 CW: So it varies quite a bit. And we try to play to the strengths of the people we partner with to hire, so some people are going to primarily work their personal network, and that network is really strong in a geographic location. That’s okay, we just wanna understand that going in, so that we can know, “Hey, if you’re really strong at recruiting in San Francisco, but maybe not so much in Houston or Dallas or Denver, or whatever, that’s fine. We just wanna make sure that we’re balancing our recruiting efforts and that we’ve got resources in different areas.” So same for a hiring manager, I have a hiring manager, an engineering manager, she has a fantastic network, it’s primarily fantastic in Texas.

24:32 RS: Right.

24:33 CW: That’s awesome because we hire in Texas, but we wanna make sure that she’s got the right partners and support in case we do have a role that we wanna fill in San Francisco to keep the team balance. So it’s just all about setting up the support the right way.

24:47 RS: Yeah, it makes sense. You are quite invested in recruiting and hiring, which is music to the ears of your recruitment team.

24:54 CW: Yes.

24:55 RS: I’m curious, and you also mentioned that you’ve taken it upon yourself to go and persuade people in a [25:01] ____ concerns in the event that they are hesitant about remote work or creative market. Do you have a memory of a really great candidate? Maybe someone you wanted to get for a long time, or someone who you helped realize it was a really good fit despite their misgivings?

25:18 CW: You know, actually, yeah. One… Another one of my engineering managers, he… I remember our first one-on-one, and I said, “What do you… What are you scared of? What are you most worried about?” And he said, “Honestly, I’m most worried that I have not worked remotely in a long time, and I’m worried that I’m not gonna be good at it.”

25:39 CW: Yeah.

25:39 RS: And… And he’s great at it, but he had to go through that process of self discipline, setting up the process, working through it and so, he was really excited about Creative Market because of the product and the team for all the right reasons. Going from working in an office to working remotely, it worked for his family and so there was something good there, but there was also just a lot of concern about it like, “Oh gosh, what if this doesn’t work?” And it did, because we set him up the right way, because he did the right things in his day-to-day and so it worked out. But we have not… We’ve been really lucky in terms of pitching. If someone’s excited about Creative Market, and we’re in touch with them and we’ve got that momentum in the hiring process, and the cadence feels really good, we rarely, finger, knock on wood, we rarely send out an offer letter that’s not accepted. Very, very rarely. So we’ve been really lucky over the years.

26:41 CW: This also speaks to the multi-disciplinary nature of recruiting, and so they might have to, or even for hiring manager, have to put their sales hat… And this is, objection handling. And in some cases if you don’t have this empathy, if you’re not having this conversation, you might never even realize that that was an issue for someone, and then they say no, and they’re saying no in a vacuum, there’s no insight there, you don’t have to opportunity to address that concern.

27:06 CW: And it’s a really tricky balance because at the end of the day, our job is to get talent in the door that we think is a good fit, and we do wanna tell the story of Creative Market, and I’ve got a personal story about why I’ve been here for as long as I have been. But, at the end of the day, if it’s not a good fit there is also an objective hopefully, objective analysis there too, where if it’s not a good fit for them, it’s actually in both of our interests that we not move forward. And so, there’s an art to the pitching part of it. I almost don’t like… I keep using it so it’s my fault, but I almost don’t like that word, because what we’re really doing is just conveying our values, and what our company is about, and if that feels right, great. And if it doesn’t, thank you so much, and we’ll move on…

27:53 RS: Yeah.

27:54 CW: Because…

27:55 RS: Not a fit.

27:56 CW: Not a fit, and that’s okay. Even from the remote perspective, we even are very careful to set expectations around travel up front, because yeah, we are a distributed company. We also like getting together and working in person from time to time. Are you near a major airport that has a direct flight to San Francisco? ’cause we don’t wanna put you through a 10 hour a day.

28:18 RS: Yeah.

28:20 CW: And sort of vetting out those things really early on in the process there. It’s like a 3 second question, it’s a quick conversation. It is so important because if someone’s gonna work at the company for years hopefully, they’re gonna have that experience, again, and again, and again, and the only time to catch it is before the offer letter goes out.

28:39 RS: Right. And in some cases, the only time to catch it is once you’ve made the mistake and hired someone for whom that was a big problem, and then maybe the hire didnt work out, or maybe that you placed an unfair stress on them, and now it’s too late for them, but that’s probably on the hiring manager to communicate that feedback to recruitment. And you need to find this out earlier in the process, just because it’s gonna be an issue for someone.

29:05 CW: Yep. That’s the other reason to do this early. It’s not always that simple, ’cause not everyone is always at the beginning starting the company, and it is harder to bolt it on, but that’s one of the reasons it is harder to bolt it on, because you’ve got all these great people, but they might have a bad connection and you work with that. There’s a transition period, you can set up policies and you can make it work a little bit, but ideally, you’re going into those conversations at the hiring step really intentionally, so that the whole company is set up for success, that way.

29:45 RS: Definitely. I love it. Chris could keep talking about remote all day, but you have a life to live, and a job to go to, and a new baby to raise so I’ll let you go on with your life, but thank you so much for coming in here and chatting with me.

29:58 CW: Yeah, it was great talking to you, thank you.

30:01 RS: And to all of you out there in podcast land, that just about does it for all of us here at Talk Talent To Me. I’ve been Rob Stevenson, Chris Winn has been Chris Winn, and you’ve all been amazing, talented, beautiful recruiters have a spectacular week and happy hunting.

30:24 RS: Talk Talent To Me is brought to you by Hired. A double opt-in global marketplace connecting the best fit active talent to the most exciting recruiting organizations. If you would like to learn more about how we can help you find your next great hire, head to, and we’ll get started.