Cloudflare's Creative Corner
The Creative Corner explores the experiences of creative professionals working within the tech industry. From challenges faced to lessons learned, we will join them on their journey as they share their wisdom as creatives in tech.
Hey everyone, welcome to the Creative Corner. My name is Jess and this is Dylan and we are waiting on our guest, James, who is joining us here in a couple minutes.
We're just trying to get our passcode squared away here. We're on mute. There we go.
All right, we're in business. That's exciting. Sorry about that. I was going to say, your dog's just like passed out over there.
Yeah, I'm going to close. It was quite weird because I could see what was going on.
Oh, really? I could sort of see the panic on her face, being like, we're live!
Jess and Kurt, you two are like a little bit together, just sending me a million emails saying, try this, try this.
I don't know how you finally figured it out. Nobody would have seen, they would just have assumed that this is like graceful, high production TV.
But behind the scenes, there was a lot happening, wasn't there, on that keyboard?
There was a lot happening, yeah.
And we have an incredible team who was helping us figure it out as well.
Thank you to Jason and Kit who helped us troubleshoot that. Thanks for joining us.
It's so good to see you. Oh, and you, you've got yourself set up there.
Look at that room. It's coming along. A bit of Antony Borrell in the background.
Yep. There's some dogs, I promise they're alive. They're asleep on the ground.
We don't look very alive right now. But I'm really excited to introduce you to my colleague Dylan here.
Dylan and I have been doing this show on Cloudflare TV for the past month or so.
We've been having a ton of fun and we're super excited to have you.
Yeah, it's really great to meet you, James. Lovely to meet you too, Dylan.
Whereabouts in the universe are you? Floating just above, I think, Australia right about now.
Figured this might be a more pleasing background than the last few segments where it's just been my blank white kitchen cabinets.
I feel very Zoom background redundant.
Well, thanks again for joining us. We're super excited to hear about what you've been up to at Pinterest most recently.
It would be great if you could give us a little rundown of what your journey looked like prior to joining Pinterest.
And then obviously want to hear about your newer adventures there as well.
Perfect. Well, I'm James, Global Creative Director at Pinterest.
And yeah, what is my journey? I think like a lot of people, it's an unusual journey.
I've spent time setting up my own design agencies. I've always worked agency side.
This gig at Pinterest is my first time working in-house somewhere.
So I've worked at all sorts of different agencies. I have run a very small agency.
I run an illustration agency, set up a type foundry like mid 2004, I think, 2005.
I have worked in branding agencies, worked digital agency, sort of the height of the digital bubble, dotcom bubble.
And then sort of by my persistence, I ended up working for an agency called Design Studio, where I was for a really, really long chunk of time.
And that took me on a journey from London, where we grew the team considerably into San Francisco, where I got to meet the lovely Cloudflare crew.
And then setting up a studio in New York. And then about a year ago, I literally cannot believe it is a year.
The team at Pinterest thought they would take a gamble and see whether or not I have sort of any impact there.
And it's been a ride.
It feels like I've been at Pinterest for about 20 seconds, but also for about 100 years.
Compounded by COVID, working from home stuff, time has become incredibly fluid.
Someone described it to me as every day is just a time soup. Now, I feel like that's very accurate.
Yeah, there was a saying, there was a saying that we had actually a design studio where it felt like a day could last years, but a week would go by in a heartbeat.
And, you know, you just couldn't believe the number of different things you sort of do.
I sort of feel it's a little bit, I'm not sure that it's quite the same, I sort of feel it's a little bit Groundhog Day-ish.
You know, like sometimes there's a cafe, I've got three kids, and there's a cafe near us that I take them for a walk most mornings.
And it closes on a Tuesday. And that's always become like the marker for me.
You know, when I get to that cafe, I'm like, oh, must be Tuesday.
That's like the thing that sort of denotes how time is moving. Hopefully they don't close on any other random day, that would be super confusing for you.
Yeah, I know. I mean, if they mess up their schedule, that is it. That's my last anchor, the last reality.
So you work at agencies for a very long time, quote unquote agency world, now you're at Pinterest, obviously.
What has been the biggest shift for you in making the leap from agency world to in-house?
I think a lot of people were nervous when I told them I was going to move in-house.
They were really nervous whether or not I was making the right move.
Because I think I've got a very, very short attention span.
And I think that that sort of works really well in an agency where you're given these problems and you have to run at it really, really quickly.
You have to run at them really quickly. And the metaphor that I keep coming back to is how you get this bit of clay.
And very quickly, you've got to mold this bit of clay into something.
You tend to get a little bit of like, you know, it's quite good for the ego because a client has usually said there's something wrong with our business in some shape or form.
And then they've gone through a lot of pain and heartache to get to a point where they talk to an agency.
An agency comes in and you get to wrestle with the ugly bit. And usually you're the best meeting of the week.
So it can feel sort of very, very rewarding.
But the dopamine hits are like short and sharp. And then, you know, you see the work and the great chat and the sweat and tears that you put into something.
And then a few months or a few years down the road, you're like, what happened to it?
What's going on there? And you sort of, you see it sort of gently declining.
And I think going in-house, we've just got this massive bit of clay. There's like hundreds and hundreds of people sort of hitting this bit of clay from all sorts of different sides.
I actually feel like it's more, those dopamine hits are sort of more, you have to sort of look at it slightly differently because you sort of, you're having to work out, are too many people pushing this big lump of clay on the wrong side?
Or are we sort of, are we all pointing in the right direction?
We all understand what this bit of clay should be. And you're sort of, you're always in that sort of grind of trying to mould this much bigger thing, in terms of a bigger thing into something.
So yeah, I definitely do miss the short wins. Something we're trying to work out is how do we make sure that we celebrate and put in real mile markers as a team?
And I don't know what it's like at Cloudflare, but I suspect it might be similar where it's so gargantuan.
That's a funny word to pull out, isn't it?
I think it's your background, and I'm going to start using three syllable words.
It can feel really, really overwhelming trying to work out how you're going to move this thing forward.
And it can feel really, really incremental. You know, you take a step back and you're like, hang on, how have we only moved this far?
When I've been in meetings, I've had to push all of these different pieces in so many different directions.
But then you realise that there are so many different bits of this puzzle that have to move.
And there's so much, you know, the thing that I'm most proud of this year with the team of Pinterest is I feel like we are a real team.
And there's a team of people that believe in the mission. You know, we're here to help people live lives that they love.
And to do that, we want to feed them, fill them up with inspiration.
And that's a really sort of worthy thing to get up and sweat about.
The thing that I also have learned to love is that every single person that you talk to thinks that they're right.
And there's sort of this, you know, I'll walk in and I'll have my sort of point of view and you're talking to 10 other people and every single person on the table thinks that they're right.
And it's the ongoing negotiation of how you take the best bits of all of those, all of those conversations and all of that learning, all of that understanding and get something that's greater than the sum of its parts.
And I don't think you really get that.
You sort of get that in a smaller way in an agency where you get, I think, because the problems are distilled a little bit more clearly.
And there's usually an end goal with most of our sort of projects.
There's usually like an end goal, like we need to launch something.
We need to resolve this thing or whatever. Whereas with inside, inside the machine, like the end goal is actually much loftier.
And so you've got all of these incremental steps to try and get there. I feel like I'm learning sort of loads, loads, absolutely loads.
There's nothing more humbling, I think, than going into, you know, Pinterest is a very reflective organisation.
And you spend a lot of time sort of reflecting on how you as an individual are doing, how your team is doing, how the broader company is doing, how society at large is doing.
I think that process of reflection is, you know, it should be a really humbling one.
And it's a time to sort of take stock and look at stuff and make sure, like, what do we need to do and put in place to either be a better company?
And I think the way that we're sort of reacting to things like COVID and the tools that we've been putting out there.
I don't know whether you've been following, but we've had a fantastic set of creators helping make these sort of absolutely bonkers masks.
I feel sort of very humdrum now, with my little black fabric.
I realise that's not stepping up to the plate. Through to the election cycle.
How are we going to, how do we be a responsible corporate citizen through this process of having this thing that, you know, as an English person living abroad, I can't believe the swerves that this election is already taking.
But I'm sort of, I feel so rewarded to work for a company that's come out really clearly and said, you know, on this platform, we're going to make sure we push people to trusted resources.
We're not going to, I don't think Pinterest has taken political advertising for a really long time.
And they're showing real leadership in that.
So there's all of that sort of stuff that makes you think, all right, at a meta level, this is good.
And then it forces everyone at a micro level to be good in that world, which I think is, again, that's a really big change.
What's it like at Cloudflare?
How do you two feel? Jess, do you want to take that one or do you want me to?
Yeah, I mean, I spent the first half of my career working in agency world, and I can totally relate to what you said around the dopamine hits.
And there were many spikes of that working for different types of brands and clients and campaigns.
And it was kind of just all encompassing.
And I think it was probably having to be exposed to a lot of different brands as well versus one brand and getting to kind of like dip your toe into a lot of different pools.
And so the dopamine hits kind of came in that way, I think.
But then coming in-house, it's like versus working in agency world. In agency world, you don't really get to live the brand through its lifespan as you do when you're in-house.
And there's something really special there. So at Cloudflare, it's like I've been at the company for almost four years, which feels like more than a decade because the company has grown so much.
We've experienced so much and went from startup to now public company.
And it's been really wild and rewarding to get to experience a company throughout its life in that way versus an agency world being part of the ride in very short spans and stems for different brands.
So it's very different and rewarding in different ways, but I think slightly more rewarding being in-house, especially if you get to stick it out for the long term.
Cloudflare is my second in -house position. And prior to that, it was all design agencies leading up.
And for me, I liked your metaphor about the clay and whatnot, because at an agency for me, it always felt like working with that small bit of clay.
And while you do get those quick hits of satisfaction of being able to work on a ton of varied material.
For me, I always wanted to see the like, and what next?
And it always felt like working on a small piece of a much larger pie.
And it gave you a lot of breath in terms of the stuff you got to work on. But I always wanted to see like, OK, what's the next step?
Here's the MVP product. Here's the first iteration of design.
What's the next step? How do we scale that larger?
And moving internally, for me, gave me that ability to kind of like, see that design at inception and then work that scale all the way throughout the company across multiple channels, etc.
And that was kind of my biggest draw. That was one of my biggest pieces of enjoyment reason for shifting internally.
It's like now I look back at those agency days, and I'm almost embarrassed actually about sort of the hope that I had for some of the work and the way that you deliver the stuff into a company.
I almost wonder whether there should be a part of working in an agency where you have to work in-house for a while to understand the different ways that those projects have to sort of move through and how you make an idea.
The simpler the idea, I still believe the simpler the idea, any idea, the stronger and the longer it will endure.
And I think that there is like a thing when you're in an agency where you're like, I'm going to bamboozle people a little bit.
So you get a bit more mastic with where the ideas get, and you can sort of see how they get pulled apart as you move through.
Maybe we should set up a boot camp for people who work in agencies who want to do work for big companies.
I think there's a lot. Interesting model too, because I think obviously we worked with your team at Design Studio on the refresh, and the project took a lot longer than anticipated.
I think because Cloudflare was such a beautifully complex brand to grok, and along with a lot of other initiatives we had going on, the project took over a year.
But at the same time, it's a brand that has so many different angles and many meanings and many audiences.
And reflecting on the project, I'm like, would it have been more successful if we had an agency team embedded internally with our internal team?
Like some sort of hybrid where the folks at the agency can really live the brand, they can experience it day to day, they really understand the essence of the soul of the company.
I think that's what's so special about Cloudflare, like the employees can feel the culture every day.
And there's something very special and electric about the culture at Cloudflare that's very hard to articulate to an external agency.
You probably experienced that with all the brands that you worked on in the past too.
I mean, yeah, we, I think we prided ourselves in becoming, or tried to become embedded as much as we could with different brands.
But that's what I can say now, a year into Pinterest, and I think this is, it's really difficult to get right.
But what I'd love, you know, we're a small but mighty team within Pinterest, we're about 30 odd people.
And what we're trying to do is we're trying to much more clearly delineate ourselves as an agency within the organization.
And that's not to say actually there's a separation, you know, we're within a marketing organization.
And there's a lot of cross-functional teams that work very closely together.
So it's not to sort of separate that out.
But it's more to make sure that we can incubate good responses. And there's a bit of critical distance within the organization.
And I'd say that's almost like another really big difference between agency life and being in houses.
In an agency, you meet, you know, there are these moments where you come together with whoever you're working with.
And so you've got like this drumbeat of when you're going to have to formalize, like your thinking goes from soft to hard.
And when it's soft, it's fungible.
And you sort of let in different ideas. And, you know, an idea can grow, an idea grows.
There's like usually a small squad. And you can be very vulnerable with each other.
Because I think when you're in house, there isn't, you don't, or certainly my experience with Pinterest, there isn't necessarily that same sort of soft to hard fungible process.
Because you're in meetings all the time.
You're in, like, it's quite delivery mode all the time.
And so people don't want to sort of, or don't necessarily feel comfortable to be totally vulnerable in that situation.
It takes time to build up that sort of trust.
And maybe I'm holding, maybe the rest of the team are fine with this. And this is just my own insecurity coming out.
But, you know, so what I'm doing is get to a place where I feel really comfortable and can model that sort of behavior, where we say, right, this is like a safe space to be really vulnerable.
And let's say the really stupid stuff, because out of that stupid stuff and asking those really dumb questions, I think we'll get some real insights that will let us push whatever the thing is we're trying to resolve into an unexpected place.
Whereas I think when you're in hard delivery mode, you end up thinking about, all right, this is what's expected.
This is what's expected. It's a very hard sort of push to push outside of it.
It's fascinating. I'd say that that's been like the big transition.
You know, I've talked a lot, I think, about being a coach and not a player.
You know, as you become a, as I started to spend less time actually designing things and spent more time working in teams of people designing things.
At first, I, so it was sort of very annoying. And I think my wife and kids will testify that I spent so much time just making other stuff.
I think because I was sort of, I felt drained.
I was like, I'm not making anything at work. But then you sort of, you realize actually that's the thing that you're making.
You're making a space to make work.
I think that's why that took me a long time to get right.
I think I'm a long way from being in any way the finished article, I hope.
But I think like working, how do you make space for people to make great work? And that might mean being a really, really good advocate.
If you don't believe in something necessarily, but you know, you've got to build trust with whoever you're working with.
But then you've got to turn around and you've also got to be a really good leader.
You've got to say, listen, I know I just said that was amazing, but what if we just tried this other thing?
The best creatives I know have got very, very high EQ.
And that's a gift and a curse. The gift is, you know, you feel a lot.
The curse is you feel a lot. By helping people sort of understand them and go on the journey.
It's something that I mess up every day. Yeah, that might arguably be one of the more important aspects of leadership is the EQ angle.
You know, it's very hard to teach if you don't inherently have it.
Yeah. Yeah. Yeah. Sorry.
I was gonna say, you know, the model you were talking about is really interesting.
And I love that idea of trying to craft that space for the team. And, you know, I'm wondering, moving to this global position, you know, what are some of the challenges or successes you've had, you know, crafting that space, instituting that model, you know, across multiple geos, cultural standards.
Design with everything that Pinterest, you know, Pinterest brand touches.
I can talk about some failures.
Let's see if we get some. I feel like you learn much more from those than you do from the like everything went great.
There wasn't any problem. Yeah. Well, through the interview, when I was interviewing at Pinterest, one of the people I met is a guy called Naveen, who I think was very early at Pinterest.
And he gave me the best bit of advice, actually, through that process where he said, you know, you're coming into a company, not because we've got it all resolved.
You're coming into the company because there are big things to resolve.
And I think that was like a real like, oh, OK, that's interesting.
So the things the big failures in terms of moving into like trying to work out now a team that is operating like Pinterest.
I think I brought my agency hat into the room. And by that, I mean an agency.
You know, I started agencies. I think when I when I first started a design studio, I had to do my first pitch for design studio before I even worked at the studio.
You know, it's like I took two weeks off before I started.
I was in my wife's family house in Cyprus.
And I got an email saying, look, we've got a pitch. It's like the day after you start, you might just.
I think that's kind of expected. And, you know, you land and you deliver and you don't deliver your app.
And it's like hard and fast and stuff.
And I sort of I bribed in that world. And now I came to Pinterest. I think I sort of brought that with me.
And I sort of went on a very confident roadshow around the business, telling people what we were going to do.
And and lots of people, I think, sort of took it with a pinch of salt.
And so one of the founders said, you know, just give yourself a year.
Like it'll take about a year for you to really get there.
And I actually think that's the best advice I've got.
So I'm still getting the letter. And I think that that is sort of an interesting and interesting thing.
So I'd say not trying to rush to solutions or that that can sometimes be damaging.
And I think the other thing is I have always focused on the output of the work.
And it's like. If you know, what do we do? What do we get out of the way to make sure that the work is great?
And then an agency, that's really easy because, you know, it can be the reason why I think agencies can have quite high attrition rates because it's quite brutal or it can be quite brutal place to work.
And I know that I've certainly been very unforgiving in certain situations around my day.
The work's not good enough. This isn't the right place for you.
I'm not going to be able to help you. I'm not sure this is the right place for you to work.
And the thing that you realise working in houses is a totally different dynamic.
Actually, it's much more about getting a culture of trust and safety.
And I think it's taken me a long time to really sort of get my head around how that whole model works.
But it's a much more positive model. And I'm sort of again, that's something we do set up a boot camp.
I think there are a lot of learnings from that that would be really, really beneficial for agency.
We we the global the global component is interesting.
Most of our team are based in California.
We've got some members that are based in and I'm talking about my team specifically.
So whilst we're mostly based in California or some people based in New York, we support people who are working all over the world.
And I think that's actually where the power of a brand like Pinterest is really, really powerful, because the sort of the design of the system is pretty impressive.
You know, the number of people that are involved in making sure that each country is represented and is understood with people on the ground who are from that country and some of the nuances of cultural needs of that country.
And that might be the brands that we might work with or how we might partner with a brand or we'll often come up with ideas for how we might tell a story or come up with a campaign.
Now, how do we take the right bits of that and tune it and make sure that we're being socially relevant, culturally relevant in whatever country that we're sort of landing?
And I think, you know, the other key thing is being an inspiration company.
You've got to be plugged into what is going on culturally.
And I think the ability for, you know, there are amazing feedback channels internally within the organisation that actually gives lots of different people quite a lot of opportunity to craft an idea for something and then run with it and sort of bring that thing to life.
We've seen, you know, in the short time that I've been there, we've seen an entire editorial aspect to the platform to introduce.
It's called the Today tab, where every day there's sort of these doses of inspiration.
There's a team of people for small business and small businessmen.
We were starting to craft a whole bunch of places that we could start to talk about some of the tools that we're developing for brands that you can shop on the platform.
And for Black History Month, we just made the entire focus on black small businesses.
And it's amazing.
I was just going through and doing some shopping, actually, just before I jumped on the call with you.
You know, it's an amazing way of seeing how a brand can.
And actually, I'd say that's one of the things I believe in. A brand isn't something that sits in isolation.
It's something that responds to the world that it lives in.
And I'd say that global aspect is a two way venue. It's not just the brand talking to other people.
It's also us listening. I think those are examples of the brands and appearing like this is what we need to be, what we need to be talking about to be relevant.
And then finding ways of sort of believably and meaningfully and core to our own mission, engaging with whatever that whatever that story is.
And if you've not seen it, I do think that the sort of I think if you just type in Pinterest Shop, there's a set of boards that are fantastic as a sort of a window into what that could look like or should look like.
Very cool. Are you able to share what some of the ways what some of your listening tools and channels are?
That's very interesting to me, especially at a global scale, because obviously different cultures are interacting with the platform and brands.
And how do you get those cues in them to help you and your team make decisions?
Well, we're really lucky because we've got an amazing insights team.
And so those insights come and it's absolutely astounding.
Some of the ways that they can sort of talk to us about what the world is looking for on Pinterest.
So some of it is obviously what people are looking for on the platform.
And that's been a sort of a humbling experience because Pinterest, you know, we will often use language like Pinterest for planners.
People tend to come to Pinterest and you've just moved, Jess.
I don't know whether when you moved, you started to plan. I've got many interior decoration boards.
Exactly. And I think that that's kind of a really common way that people use the platform are dreaming about what they might want to do.
And it's sort of a really useful way of sort of going on a little like, hmm, is this going to be where I'm going to work?
Or is this where I'm going to, you know, it's like it lets you sort of make these mental leaps very quickly before you commit.
So people tend to plan early and they plan a lot on Pinterest. And we saw over the whole of COVID, it became much more immediate.
Sorry, I think we'll be here.
I'm one of my kids. Not very happy right now. Sound proof a room. So we saw over COVID, all of that planning became much more immediate.
The needs became much more immediate.
I'm like, what can I put today? How can I entertain my kids today? What's really, really gratifying and some of it, you know, made you feel quite sad.
The things that people have to sort of look for right now.
And now we've seen that totally shift back into planning.
But the plans are getting more and more and more exciting with this holiday season in particular.
You know, there is so many sort of amazing dream holiday scenarios coming together, which is kind of fascinating.
So that's a really, really key component. How people are using, what are people looking for on the platform?
The other thing is we've got lots of outreach with Pinners.
We call the community people on Pinterest. The Pinner community, they arrange and set up their own events where we tend to show up where we can.
We've got an amazing squad of people that are always interacting and engaging with Pinners.
And the thing that most, I mean, I don't know why I was so humbled.
I didn't realize this before I started, but Ben, the founder and CEO, he still meets with a Pinner.
He has lunch with a Pinner every, I think every month.
And then we'll write this sort of real thoughtful what he learned in this conversation.
And I think that that leadership from the top, like let's never forget that we're here to serve this audience.
And it's not something that people say, but it's actually something that people live, sort of percolates throughout the entire organisation.
So I'd say, how do we keep on top of it?
Some of it is like there's an insights team, that's their job. They learn about what people are saying and help us feedback.
And some of it's sort of soft stuff, like people sort of being engaging.
So that's how we learn about the Pinner stuff.
But then there's all the stuff that happens outside of Pinterest. And I think we, I mean, again, we have a bunch of people all pulled together on what is happening within the competitive space.
But actually the most important thing is everybody within Pinterest being curious and interested about the world that we live in.
And if we can use that sort of hive mind to stay on top of this is what's going on in a certain place.
And we've got channels like platforms that people can share that thinking and have visibility about what other teams are working on and have the opportunity to share their own points of view on it.
I think that's a really powerful way for us to always sort of push and pull.
We've got, I think, over 3,000 people spread around the world.
And a fairly substantial sort of crew of people that we can have pushing us and prodding us as a brand to help push the entire brand forward.
I'm sure there are other more sort of tangible things as well.
Yeah, that's awesome you have an insights team. Are any of those folks on the marketing team?
Yes, the insights team is actually within the marketing organization.
Wow, amazing. That is really convenient. Yeah. How big is the marketing org?
It's over 100 people.
And, yeah, I mean, it's a considerable number of people. Thinking about how we make sure that Pinterest is building a platform that's good for pinners, how we're building something that's good for brands that we hope will work with Pinterest.
And our newest sort of audience creators are the people that we hope to create on Pinterest.
And I think that that's going to be the big push that we will see much more of as we start to roll out some of those tools to help people create content that's going to be native for the platform, which is, I think, the most exciting sort of aspect of where we're at.
Yeah, that's super exciting.
Are you able to tell us anything about how the marketing org is structured?
So org design has been top of mind for me. There's lots of shifts happening at Cloudflare.
We're growing really fast, always. I'm always looking to learn how other marketing orgs and creative teams are structured.
So any insight there would be awesome.
Yeah, well, there are. I'm going to butcher this, I'm sure.
I've been on paternity leave for about two months, so do also forgive the fudgy brain.
So there are marketing leads who own specific audiences.
So there's marketing lead for business, marketing lead for creators, marketing lead for pinners.
Those marketing leads are supported by people who work across all of the different functions.
So there's an insights team that supports any of the marketing leads.
There's my team, creative team that supports any of the marketing leads.
I think that that is it. Oh, sorry, there's a content team that supports all of the marketing leads.
And so once the marketing leads will go sort of as a vertical, they'll think about the different things that might need to happen.
We'll support up and down that entire vertical set of messages or tools that they might need to produce.
And then we all report into probably the most inspiring person I've ever had the pleasure of working with.
Andrea Mallard, who's the CMO. And if ever you ever come across her, she is, I don't know how she finds the time or the energy, but she seems to be sort of plugged into absolutely everything that Pinterest is doing and involved in, whether it's sort of the smallest detail through to the biggest challenges that we're facing.
She's sort of been a very, it's humbling to work with someone who's got that sort of energy.
When I first started, I would joke with her and say, if ever there's sort of a power failure, like the power stations all go out in America.
I think she's plugged them into me because somehow she's got this like internal atomic clock that sort of keeps things trucking.
And then she's sort of our representative at an executive level, making sure that the stuff that we're doing is on point for sales, engineering and leadership thing.
Do you have specific design teams within your org that are dedicated or embedded with a particular marketing channel, like a core pinners group of designers, a core creatives group of designers?
Yeah, when I first started, that was actually how it was set up. And I was worried about that.
This is actually not a mistake. So, yeah, we had a team of people that were focused on pinners and a team of people that were focused on businesses.
I was worried because I felt like people were building two slightly different brands.
You only need to move sort of 10 degrees in different directions.
Suddenly you get quite different things happening. So I wanted to bring the entire team back to a place where anybody on the team could work on anything, whether it be for a creator or a business that we could possibly do.
We plan sort of six months out usually.
So we've got like pretty good line of sight on what we need to work on.
So we can say, right, this team has been working on pinner stuff for a while.
Let's bring them into something that might be happening for the business community so that we make sure there's sort of not a brain drain.
We don't get a siloed way of working.
Now, the mistake I made is I used the word pod to try to describe the intention was to create a way for us.
To your point, actually, about how do we stay in touch with stuff going on outside of the world?
To try and create a way, a forcing function for people to not just think about the challenge that we've got internally, but a forcing function to think about the challenge externally.
So we had an innovation pod, for instance. And the idea is or was that we would have a group of people that would think about innovative partnerships or innovative ways of working, things that other brands are doing and bring them back to the team in parallel with whatever it was that they're working.
And that slightly went sideways. And suddenly we had six pods and people like, oh, I'll just do stuff.
I'll only do innovation stuff in that instance. I don't need to pick on them.
And that was a bit of that. That was a bit of a learning, actually, because that was my mistake in being pretty woolly with the role and intent of what this, what the power of that nomenclature meant that people sort of took the pod as sort of a job description.
And we ended up having to have all sorts of conversation around what that meant and how we how we sort of move forward.
Now, we still have those pods, but that's sort of on the big hit list of things that I need to resolve.
Is that organizational design within the team to make sure that we get the best bits of people feeling like we have ownership and agency over the different aspects of, you know, the Pinterest brand at large.
But also make sure that culturally there are ways of ensuring that as a team, we all stand by to stuff that's going on outside of whatever, you know, bubble that we might be working in.
And yeah, I don't know. How are you thinking about it? What's it shaped like at Cloudflare?
We're, I would say, kind of similar in a sense.
When I joined Cloudflare, it was a little bit of people working on just, you know, anything and everything.
But people had started to kind of self-orient towards, you know, defined workflows that I think best suited their talents, their interests.
And, you know, from our perspective, I think that was difficult for us to execute on just because it inevitably led to anybody in the company just kind of asking, you know, their friend, the person they get coffee with the most, or whatnot, to do their design work.
And it became very difficult to plan projects out and get, you know, identified capacity for the group.
And so we started to shift and lean into that kind of specialization almost where we created distinct channels that could work and partner really closely with the group's most, you know, representative of that channel.
And really be able to deliver, like, understanding and meaningful work for that channel versus, you know, kind of the surface level material.
So right now, we have a kind of pseudopod structure, more specific design channel structure, where we'll have a group of designers that work very closely with the product marketing and DG groups, a group of designers that work with our EMEA and APAC offices.
And, you know, they're able to, like, sit in their standup meetings, have one-on-ones with those teams, and really get intimate with those individuals and their audience and their needs.
So they can create material for them in a much more, you know, effective manner.
And then we can also plan against that much more seamlessly.
But I do like that notion about, you know, a downside to that model is definitely that idea of brain drain, you know.
And from a creative standpoint, we really want to avoid, you know, anybody feeling burned out in the sense of, if I see one more product marketing-oriented piece of design, I'm going to go crazy.
So, I mean, that is definitely a challenge that I think we try to solve through, you know, fun culture activities, and the fact that I think we're very open to allowing designers to, you know, work cross-channel on projects.
If there's something they feel particularly passionate about, or if there's a particular channel that is saying, hey, I'm really swamped and I need some help, we can kind of, like, spot designers that are going to cross channels pretty easily.
So there is that varied level of work, I think, for everyone. Yeah, that's actually an interesting difference, again, between agency life and in-house life would be, you know, in an agency, or I don't know if it's true for any agency, but certainly any agency that I've been involved with, we've always tried to make sure there's a real sort of ideas, the best ideas come from unexpected places.
And sometimes we would have to do, like, you know, sometimes you have to design culture or design things to create the culture you want.
So at Design Studio, we did a thing where interns would teach us something.
They would, like, force the sort of inversion of that, like, oh my God, the creative director's got all the answers, I think.
Many of us are petrified they don't have any answers. But also because the people that are graduating today are the smartest people in the room.
They're the people that I'm not sort of, they don't have the depth of all of those sort of, like, things that in our brain we think are either wins or losses.
The main people think, oh, that's the answer for something.
Like that, like, quick, oh, that's the answer for something.
It's really just like repetition. You're just like, step and repeating, like, you're thinking a little bit, like you might evolve a little bit.
So I love it whenever I'm in a room with someone who's, like, the closer you can get to when someone's graduated, the more enriching, I think the entire business world can sort of be turned upside down, the more enriching those conversations are.
Because the ideas aren't tethered to all of those things that are perceived to be issues or barriers, necessarily.
And I think that, so in an agency, we, you know, we might be really struggling with a particular brief, you throw out the entire company, whoever comes up with something, anybody, there's something in the team.
You know, like the team sort of moves and you sort of, you swarm around whatever the particular problem is.
But I think in-house, maybe it's because the planning is, you know, there's a lot of line of sight of all of the jobs to be done.
So it means that you sort of, people get into a bit of a groove.
And I think that groove, the deeper that groove gets, the more dangerous it can be, because it's harder for people to say, oh, how can I contribute or how can I add value to whatever other project is happening.
The things that really, really worked at our end have been having a couple of sort of formalized meetings where we get everybody in the team to just put up work, talk about it.
Sometimes it's fast paced, sometimes we really marinate on a particular project.
Sometimes it's something that's not going very well that needs lots of help.
Sometimes it's celebrating something that's already gone out.
Just like making sure that everybody in the team sees something that a bit of the team have done.
Everybody has a point of view and says something, feels like they have ownership of it or that there are bits of it they disagree with and they can air those grievances.
Or there are bits of it that they say, I can steal that thing and I can use it over here.
And trying to make sure we keep that alive is critical.
Actually, we sort of, you know, now lots of people are working from home. So there are so many time zones to consider when you sort of set something like that up.
Having something I hope said far too many times, which sort of shows I'm not right for working from home.
So I really believe in the alchemy of the room. Like, you know, I think there's something magical that happens if you get people, the right sort of people in the right sort of room, in the right sort of mindset, I think you can move mountains.
And it's interesting in this sort of working from home thing, because you don't have that sort of the ritual of going from like getting to a space, that like initial moment where people are sort of opening up and you sort of you go from being like professional human to human human.
And then you have that moment where sort of you can be really clear minded about solving a problem or working together on a creative challenge, whatever it might be.
And I think that working from home thing is kind of different because it's like it's regimented.
It's sort of like it's on this groove. A friend of mine was saying they were meeting in a, I think it was in a Twitch game or it was in a computer game.
But I actually think that's even worse. At least it's like a different context, a different app than like Zoom or Google.
The amount of times I've been in a Zoom meeting and just thought to myself, like, if you and I were just in a room with a whiteboard and could just start doodling and drawing, I feel like we'd have a much more productive conversation.
Yeah, the science of brainstorming is much different behind the screen.
Yeah, yeah. I think there's also that weird moment where you sort of you ask someone a question, and there's that like, you can tell they're cycling through Chrome windows or browser windows.
And it's like one of these new normals of like social behavior and everyone's like, should we call them out on that?
Or it's like you can sometimes see reflections of like people's browser content in their glasses.
Yeah, oh my god. Not yours, you're totally.
James immediately takes his glasses off. When I wear my glasses, I'm paranoid.
I try to be super focused with the meeting, but, you know, something pops up and I'm like, oh, look at that, people will see it.
On that topic of remote work, I mean, that's something that, you know, here at Cloudflare, we're really trying to keep the design culture alive in this new situation.
And some of the stuff we did to build design culture when we were all in the office, you know, feels weird or just, you know, doesn't work through Zoom.
And so it's a, you know, constant exploration of what we can do to really stay connected and push that collaborative design thinking amongst the group further.
On your all's end with the remote work going on, you know, what are some interesting ways you found to ensure that you stay connected as a team and get those, you know, that collaborative thinking going?
I've learned a few things. One of the things is, I think there is like a generational thing, actually.
I actually think that some of the younger team members have taken to this much easier, easily, because I think they're more used to being like chatting online and sort of talking online and it being like just a social thing, not like a formalized thing.
So it's one of the key things is, I think the worst idea is if I were to sort of try and chair every meeting, so it'll be boring.
And I would sort of stare awkwardly and work my way through like the list of attendees and ask whatever the questions are that need to be asked.
You know, there's like working on how you loosen up and read cues and sort of deal with that sort of stuff.
So maybe it's generational, maybe it's just personality.
By working out who are the right people. There are a couple of people on the team who are just fantastic.
I've been bowled over at their ability to sort of like keep some sort of energy in the room.
There's been, I think, a bit of surprise and delight, like that moment where you click on the Zoom call and someone sort of head to toe and top hat and tails or something like that.
It's sort of like the serendipity of those moments are quite interesting.
And it sort of makes you, it takes you into a slightly different place.
In fact, I had a friend last night come over for a socially distant outside barbecue dinner.
Nice. It just happened to be right next to me. That just happened to be right next to you?
I swear to God. That's awesome. That's what I had planned for this moment.
I'm really sorry, but we did have some back channel chat about how we were going to spark off.
Yeah, at exactly 1.25. Yeah, so this guy came round last night for this socially distant barbecue thing.
And he was wearing like a blush pink suit.
It just creates like a moment of like, all right, it's good.
My life is good. Human beings are still good. So that's good. We tried a few things.
I don't know whether they, it was a bit cheesy and a bit forced.
We tried that GoToMeeting where you can book a goat to join your meeting. Oh, I've heard about that.
They take you on a... Was it lame or was it cool? Was it weird?
It was, I think it could have been cool. But I think it's obviously a bit of, I felt like it was like the farm that we worked with were obviously like doing this back to back.
And it was almost like, here's the goat. Here's the farm. Here's the horse.
Here's the thing. Thanks a lot for joining. We've got to go now. You're like, wait, wait, hang out with the goat for like five minutes.
The goat didn't even bleat.
But I think things like that, you know, might be, you know, it's quite nice, isn't it?
To sort of surprise people. I don't know actually what this is, but I do know that there is a crew of people at work that have been planning a special thing, which is involving sending stuff to people's houses and people have their addresses and stuff.
So I'm assuming that's some sort of something. So I think that's maybe the other thing is making sure that, you know, we, I'm really proud of the, like we've got a very, very engaged team.
And so people are working really, really hard to make this good, like make this as good as it possibly can be.
And people feel a lot of ownership over being an employee at Pinterest. And, and I think that's the other key thing is making sure that everyone feels invited and agency and has, not that we have to give people permission, but they feel like they have the permission to just sort of do something and take something off and, and we'll all celebrate it and, and be easy on each other in these sort of crazy, crazy times.
Yeah. Awesome. Well, I think we're almost at time here. James, thank you again so much for joining us.
It's such a great conversation. It's always a pleasure to chat with you.
Oh, thanks for inviting me. I wish I'd done more to my background.
No, your background is very minimalist, very Apple. I was eyeballing that shelf in the background earlier.
I like that shelf. Yeah, it's a nice shelf. Wayfair bargain.
Very nice. Yeah. I've been getting big on the Wayfair front. Yeah.
No, thank you very much. This has been fun. Yeah. I don't know. Do you know whether other people are watching this?
Do you have some sort of like dashboard there that shows you my mom's I don't have a dashboard.
I think last time I asked, we didn't have exact numbers readily available, but maybe that's strange.
We'll have to ask the team and I'll let you know.
But I can send you a recording of this next week, early next week.
Oh, well, thank you so much. This has been fun. What a great way to start the day.
Good luck, Jess, in your new digs. Thank you. Talk soon, hopefully.
Yeah, it was fantastic chatting with you, James. Thanks again for joining.
Oh, so lovely to meet you, Dylan. Bye, James.
All right. Bye-bye. Take care. Bye -bye.
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