Talking with Daniel Debow, VP at Shopify, on the modern workplace and leadership

May 13, 2020
To listen to the full episode, click here

Joe: (00:00)
Welcome to the DNA of an Experience Podcast from CloudApp where we discuss how and why creating an experience is so important and the psychology behind what makes an experience. So great. Thanks for joining us.

Joe: (00:18)
Good afternoon everyone. I'm really excited to have Daniel Debow with me today. Uh, Daniel has done some really great things in the tech space. He, is currently a VP at Shopify, but most recently before that had built some really cool products that are helpful. And we were talking a little bit before about a video and how things have really moved towards more of a visual space. Um, and we'll kind of go in on that and a little bit of modern workplace conversation today. Uh, Daniel, if you don't mind giving us a little bit of background on yourself, um, and how you kinda got to where you are now and then maybe talk a little bit about Shopify. You know, you had some really nice things to say before we went live. I'd love to dig in on that.

Daniel: (01:02)
Okay, sure. Uh, first of all, Joe, thanks for having me on. I appreciate it. Um, and hi everybody who's listening in. Um, I'm an entrepreneur from Toronto. Um, I was lucky enough to get recruited to join a startup right out of business school and law school and that was the first startup experience I had at company grew, went public in the 2004. I had marketing Corp dev there after that started another company called Ripple with one of my co founders at the first one. Uh, and we grew that and sold it to Salesforce and I worked at Salesforce for a few years after that. Uh, and then started another company called helpful with a far hand thrower and about a year and a bit ago, year and a half ago, we sold that company to Shopify. And both of us are now happy to be here at Shopify. Um, along the way have also done a lot of early stage angel investing. I, uh, I teach a class at the university of Toronto law school and I'm a pretty avid musician, so it's a, it's a side hustle for me. You asked, you asked about Shopify. Shopify is a eCommerce platform. It's like a retail operating system has over 1 million merchants worldwide, uh, from some of the biggest online direct to consumer, uh, merchants out there to probably someone in your neighborhood who has a small business that they want to get started. Uh, Shopify is all about empowering entrepreneurs and making commerce better for everybody. Uh, and the kinds of things I said. I mean, other than it's incredible, amazing business performance and great products. It's a really, really great place to work. Um, incredible leadership, really great culture. Um, and uh, you know, as an entrepreneur it is definitely the most entrepreneurial big, big company you'd find. It doesn't really feel like a big company now. Um, and it's truly mission oriented. I mean, the mission is to help merchants, help them and empower people to go become entrepreneurs, uh, which the world sorely needs. So that's a bit about me and that's a bit about the place I'm lucky enough to work at.

Joe: (03:00)
Yeah. I'm a big fan of Shopify. Love. Exactly what you said is really empowering entrepreneurs and providing a great platform that, uh, you know, out of the box can do everything you need it to, uh, versus having to, to build something and kind of worry about that side of the business. Just kind of worry about what you're good at. Building something and, you know, Shopify can kind of help the end to end stuff. Um, I'd love to kind of dig in on, on modern workplace. So Daniel and I connected on Twitter, his, uh, co founder of helpful, what was his name again? Farhand that's right. I couldn't remember, but he tagged a couple of different brands and one of those was CloudApp that Daniel had mentioned to him. And uh, so I reached out and wanted to have him on. But what is, you know, the modern workplace, what does that look like for you? Uh, both a tool set. Also just communication, uh, how people are kind of culturally, culturally integrated into a company. Uh, where do you kind of see, things moving?

Daniel: (04:08)
Okay, cool. Big question. I mean, first caveat is what do I know? I mean, who knows? Everybody has their own opinion. Second caveat is even if you know something, you don't know something about everywhere. And I think that's always been one of my cautions describing either the one right way to build a business. Well clearly there's lots of ways and the run one right way to build a culture, you know, clearly lots of ways and the one, you know, right future of work. So I think there's going to be lots of different futures of work and it'll change very dramatically. So I just think with that caveat, it's important to say that like, um, you know, this is going to be my view is sort of like a subset of some types of companies. Daniel danger. Yeah. Yeah. And I mean, I, you know, it's funny if, I think if you want to understand the future of work, one of the best things you can do is just look at what the kids are doing. And, uh, uh, I, you know, mentioned we had, we had started this company called ripple. Um, and the insight for ripple was that we saw this generation of millennials, this is around 2007 coming to work. Uh, and they use different tools and different modes and methods of communicating, uh, when they were, as they were growing up. And so specifically that was things like Twitter and Facebook, which kids liked at the time. Um, and so that was our impetus to thinking about ripple, which was like how could we design these new UX patterns, these new communication patterns and then build them into a work tool. And so, you know, for example, like literally the insight ripples started off as a feedback tool. We saw that people on Facebook were putting this app on their page is when you had a profile page and it was called honesty box and, and it was like, you can ask and give, get people to give you anonymous feedback at work. And I looked at that and I was insane. I was like, that's not, or sorry, just give you that anonymous feedback, not at work. And it seemed like that doesn't seem like people would want that. And yet it was one of the most popular apps out there so that, you know, always get to look at these counter-intuitive things happening from that was the insight to understand that like the way people were doing kind of HR at work was, was kind of old school and it didn't really match what the next generation wanted. So we went out with this idea and promise about understanding that and started building features and iterating on that. And you know, it resonated and not surprisingly with workplaces that had progressive, young, new, uh, workforces. And so our like flagship customers for ripple where Facebook, when they had, you know, four or 500 employees and, and LinkedIn and living social and Gilt group and HubSpot, uh, and on and on Eventbrite and when they were small companies because they did not like the traditional paradigm, the employees that they were dealing with because they had grown up with something different. Okay. So why am I mentioning that? Because I think if you want to understand how we'll communicate at work and how we'll collaborate, I think you just have to look at what the kids who are going to be in the workplace are doing today. That led us to helpful. One of the theses around helpful was that we would, um, build, uh, video asynchronous video messaging into a work tool. And you know why? Because I was constantly watching my 14 year old and 15 year old niece and nephew at the time send images to each other and pictures to each other, uh, in place of text or as an adjunct to text. And when you started to really unpack it, um, the question was like, why? Why are you doing that? And it was because if you ask them, I mean, they would say it's faster and in what they really meant is, uh, well this is something we all know. A picture tells a thousand words, right? That's like sending a simple image of yourself, you could convey a lot of emotion. And so that was the sweet spot was like, Hey, people want to convey humanity and emotion. Not just dry text and that video is a really powerful way to do that. So that was what we did. Now I'll sort of stop there because I don't have necessarily that much more perfect insight. I have some thoughts, but I definitely think that the future of work is going to involve both live video and asynchronous video. Um, and in a way that we've never sort of thought about it before. I think that's going to be part of how people work.

Joe: (08:31)
Yeah. I think there's a definitely a vision where async can quickly become synchronous as well. Like, uh, you know, you're on, I was on a chat with Apple today cause uh, something they sent was, was missing. And so I was just asking, you know, what's the status on this? And it was all text, text base. Um, but certainly it'd be easy to, like, if you can't fix someone's problem, there's a little link that says, would you like to, you know, go live with an agent and it goes to video. Um, and you, you, if you can't close it with a scene video or an ACO screenshot or something, you can, you know, go, go real time. Uh, I think, you know, that's definitely a piece of it. And also like within the workplace, we've, we've seen, you know, trends with people working remote. Obviously, uh, remote playbooks are being developed right now. Uh, we did a survey at CloudApp, uh, last fall that showed that over 50% of both millennial and gen Z generations were working remotely anyway. Uh, as far as office workers go or wanting to work remote, um, you know, the Bay area is crazy expensive. People have to live further away from their headquarters. Uh, now people may get a flavor for what remote work is like, either good or bad. So it'll be interesting to see what comes from all of this. But how do you think, you know, coronavirus all this kind of work from home stuff has really accelerated or, uh, led to, you know, a future of remote work?

Daniel: (10:13)
Yeah. Um, look, I mean there's a few things that are happening simultaneously. One is like, uh, you know, one common at Shopify. We've, we've used as that sort of our 20, 30 plans are now happening in 2020 and I think that's probably a fair understanding. We've had a giant forced transition to a new model and uh, yeah, you're going to find some friction. But I think what you're finding is you kind of basically the, you know, if you're familiar with this technology lifecycle adoption curve, um, you got people living in the future right now and you got people living in the past and usually it takes a long time for that lagger group, which is like half the population, late majority to come over. That entire population has been forced to move very quickly. Um, they might not like it, but, um, what I think will be revealed is we can do a lot more remote work and that the tools that exist today are actually pretty good. And so what you're getting then find is follow on decisions. So I, I I heard this morning a major Canadian bank was planning to basically get rid of a 40% of their, uh, real estate footprint because they realized through this experience that they could save those costs and have people work either on different shifts on more remote work. Um, and that, you know, people liked it. I mean, I won't lie, even though I can walk to work, it's about 45 minute walk. I like that I can substitute that 45 minutes on either side of the day with hanging out with my kids or you know, getting some exercise that's, that's a major change in the amount of addressable time in the day to do things I want to do. Well, that's going to happen a lot of places. So I think real estate definitely a place that's going to shift and people are going to be aware that they can do more distributed work than they used to do. Uh, and then they can use, you know, in person time selectively. I think another effect that we're going to see is going to happen over the next, say six to 18 months, is there's going to be a ton of capital put into really making these tools really good. So I, I think as much as we've been living with Skype for 20 years and things like that, cloud app, helpful, whatever you want to call it, they're still very early on figuring out how to build an environment where people work. Um, uh, let me give you an example. Like the, the laptop that you're using or I'm using, the main goal of it is not video conferencing. So the camera's okay, but not great. The microphone's okay, but not great. Um, even zoom, right? Which everyone loves because it's easier and faster, you know, it's still a lot of steps to get going relative to, um, you know, I pick up the phone and say hello or I dial a number and I'm talking to you. And, and, and we, we still haven't gotten to that place. Now. I think we're seeing glimpses of it. Uh, I put a portal downstairs in my, in my house and you know, instantly I'm tweeting that like, boy, I would pay to have another portal sitting on my desk because a purposeful design device that's really like a screen optimized for video. The cameras use in, it's got like tracking. So I can walk around, it's got a audio tracking, you're going to see money poured into these systems that make it way, way better over the next little while. So we're going to see like that this investment area, it makes a lot of sense. Um, and, and I, I, I can't help but imagine that people will adopt them. Um, you know, you can just go through the chain of areas where we can make things so much better and I think money will pour in and then you're going to see great solutions on the other side of those things, uh, for allowing us to work in a more distributed way. I think the third one I probably should say is also AR VR. Uh, I'm an investor in a company called spatial. Uh, there are many others. I'm also an investor in company called North. And you know, spatial is really working, um, to take a vision where, you know, you put an Oculus on and you're, you're teleported into the room and you can work with documents, you can work with kind of, I call it like office in the office in AR or VR. And it's amazing what was a concept. But what's interesting, and I, you know, I haven't talked to them directly, but I got to imagine all the phone calls of like, let's do a pilot or maybe we're interested, have now turned into like, we want to buy this and we want to roll out for a thousand people. Um, and so I think that's probably happening all over the landscape and that means that in about a year, I think we're just going to have much better tooling for this model of work.
Uh, last thing I'd say, by the way we talk about future of work, it's also like future of geography. Urban geographies are gonna change as people, you know, just don't need to spend as much time moving their, you know, basically their brain has to move from one spot to another. We can keep the brains in one spot and save a lot of energy by moving the brains around. That's, that's really good point. I wrote a few months ago, uh, before even all of this happened about how, you know, is the giant Google Flex a thing of the past. You know, the big HQ, that was like a big selling point for, uh, recruiting and getting people on board. And you know, a thing of the late nineties, early two thousands where you had your, a cafe and your dry cleaners and everything all in the office.

Joe: (15:17)
Now people are working from home. Uh, you know, is that, is it more the, like what you were talking about more people, this general NEC next generation of work is focused more on like balance and having that extra time at home if you have kids and really not having a traditional nine to five but more of a kind of broken up day. Well, that's a separate question I think. I think we're already living through that. Like I, I, I, um, yeah, I've always found that, you know, that line is, is a very blurry line to draw it. I, but I just caution anybody thinking about this as like, Oh, this is what it's going to be. I am pretty sure there's going to be very, very long time to come work. That's traditional work. You go nine to five, you show up at an office, you do your job.

Daniel: (16:05)
Um, we're talking about a subset of the population, but it will happen. I mean, I, um, I can see, uh, the, the changes in telemedicine in, in Toronto where I am Ontario where I, you just, you know, people are using, um, services where you can, you know, talk to a doctor right away, uh, that they would never have otherwise done. So I do think, no doubt this is going to have implications for us. Uh, but I also probably one last thing I'd say is be careful of people like me who prognosticate and be aware of like, unsafe, you know, an unanticipated things. Yep. Right. Let me, you know, when, when Steve jobs held up the first iPhone, it was about 14 years ago, I guess, and said to the world, this is, you know, Hey, check it out. It's a internet communicator. It's a mobile phone and it's an iPod altogether, you know, precisely zero people in the world at that time said, that's it for the taxi industry. Right. No one saw that. No one saw that. Putting a GPS in this thing and then having people hack apps onto it would allow this. And I think what's going to happen over the next coming years, we're going to see AR glasses coming vastly improved screens or purposeful devices for this. You know, we talked about screen, another thing that that's coming right is transparent screen. So the camera's not at the top, but the camera's right in the screen so you can look through it and you can like look right at people so that you get all that visual nuance, which we kind of lose through this thing. In fact makes it even more confusing. I think it's an, it's unclear what's going to change. Uh, what combination of technology and platforms that enable people to change is going to, um, unleash a different workforce. But I, but I think it's, it's pretty, it's pretty fair to say it's going to be very different I think.

Joe: (17:51)
Yeah, I think so too. It's just kind of, it opens things up a little bit. Uh, you may not have as much of like, uh, I'm sure you'll have more remote leadership. I mean, I know like an Adobe always wanted to have all the executive layer like right there in San Jose. Um, and a lot of tech companies were kind of that way, but you may have now a EVP or a C level who isn't necessarily in headquarters. Uh, maybe they're, they're probably, they're 90% of the time, but maybe they're based somewhere else. Um, you're able to hire outside of your footprint, a 20, 30 mile radius of HQ cause you have a playbook now of how to like actually onboard and work with remote work. I think it's just building a skill set and going to open things up. Like you said. Well you mentioned leadership, that's a really good area where I do think leaders today are going to adopt tools much faster.

Daniel: (18:47)
So one of the pharynx that we built for helpful was a product called Leadercast and it was essentially a tool that allowed, uh, senior executives to quickly record in a sort of easy way, kind of created a teleprompter on your phone, um, and manage the whole process for you with sending short video messages to their teams. And I'll be honest, like as we were talking to executives about this, it was just not in their mindset right for them. And this is sort of maybe a good, the friction around doing these things is going to go away. So today if you go to most fortune, let's call it 10,000, I don't even know if that's a thing. Fortune 10,000 companies and CEOs and you say like go record a video message. Say two years ago that was a multi-week process. It was like, let's get the script down and who are we going to bring in for video and let's get them makeup and camera right. And then they would sit in their office and it'd be very scripted. There were some that were starting to become progressive on it, but now, I mean we're going to shift to CEO walks out of the meeting and says, Hey team, I just want to share this conversation I just had with the customer and boom, broadcast it out. I think the, um, the idea that video is like this formal scripted sit down thing is going to go away too. It's like a much more authentic human thing. I mean it's really quite funny, right? Nobody prepares for two weeks to stand in front of another person and talk to them. That's all you're doing with the video. You're just talking to somebody else. But somehow that, that sort of, you know, distribution of it changes people's perception. And so I think that is going to be the harbinger where executives use video to communicate on mass much more frequently. I've already seen this insurer internally at Shopify, a lot more video executives, both synchronous and asynchronous and they're going to be using these as ways to stay connected. And it's about emotional connection, you know, like making sure that as a leader you're seeing literally seeing, um, and, and sending a short message is very different from um, sending a text. And so I think that's going to happen. I think once that starts to happen, it will signal to the rest of people and organizations. It's socially acceptable. It's professional and acceptable to give a short authentic video and you know, look like, um, my friend Mike Litt at video has been trying for a while too and, and succeeding at getting at P salespeople to use that and using video in a marketing context. And so I just think we're going to see, um, telepresence expand. Um, I think I've probably beaten that horse enough. Maybe the second part about it is with that and what I'm unpacking for you I think is an even further continuation of authentic human communication, less formality, less barriers to the leadership and more here's what's really happening in real time. Uh, and let's react. I think, you know, everyone talks about, Oh, what happened now was a shift to remote work. What probably isn't told enough is what happened now is a shift to, you have to make a decision fast. Like we didn't have time for weeks of committees on whether we're going home. I mean every major company was just forced and in governments that some did it better than others. But what's impressive to me is how many companies are going to come out of this. And say, you know what, we can actually make decisions faster and we can get shit done. Like we can do this. Look what we just did. We moved our entire 20,000 person, you know, back home. Why is it going to take us so long to make another decision like this? Um, and to me that's probably one of the most powerful things. It's not like new style of work. It's not new video conferencing. It's new decisioners agency that allows companies to make decisions faster because they realize that they can, and it also perhaps raises their expectations of dealing with big institutions and governments where, you know, it used to just be like, it's going to take forever. Um, and now the answer can be, well, like it didn't take you forever. You can do things fast if you want to. It's lack of will.

Joe: (22:39)
Yeah. Yeah. I agree. Um, and you know, you're speaking my language with the video, like at, at CloudApp. I mean, we definitely have lots of sales, uh, organizations using our product for that. And then also like my marketing team, uh, we do this like 60 second vlog about the blog, a video before every single blog post. And it just gives kind of a high level. And I tell my team or myself like one take ums and AHS, people walking in the background. Like my biggest, one of my biggest things that CloudApp is like demystifying video. Right? And how it's, it's fine. Like people, you know, I've had like, you know, my, my kids are joining me on zoom calls and it's like it's authentic.

Daniel: (23:28)
I appreciate that. So maybe another thing about the history of future of work that I think also will happen, we use the authentic but it's also like it's less duality. And what I mean by that is there was very strong, like that's your work life, this is your home life. You know, this is persona of who you are at home and your persona of who you are at work. And I think that's kind of like psychically difficult and has been for decades for people to be like who you really are and then who you are at work. And how you can say things and what you do and what this experience is doing for people is reminding us of our humanity. Now, you mentioned the kids coming on the zoom call. Not only do the kids come on the zoom call, I kind of like when my kids come on a zoom call and, well, the reason is it changes the tenor of the conversation.
Yeah. If you think about a business conversation, you don't necessarily know people and in certain cultures, North American culture, others maybe not, but what do we all do? We have like chit-chat at the beginning and what are we trying to do? We're trying to connect how the weather or what do you like this sports team? Do you like that concert? Did you see this show on Netflix? We're trying to find some commonality because it helps make it possible to have a conversation to build a little trust. That's good. Well, when you have a kid pop onto a call with a bunch of like bankers, I had a call the other day with like a big financial institution. Then my little kid comes on and what was amazing was the smiles, you know, one guy who was a CEO of a major financial institution was started smiling and he said, Oh, I got my grandkids here.
And it reminds us that we're all just people in the world as human beings and all of us are here doing this pantomime that we call work to try and help our families and get through what we have to do. Yup. And so I think that's maybe part of the future of work too, is um, it's an overworked, it's not, it's, it's removing the duality, right? You said work life balance. It's, it's more like finding, finding unity both in your humanity of who you really are and also in the way that you interact and find balance for the things that you have to do at work.

Joe: (25:29)
I really liked that. I think that's great. Kind of segue to move into kind of the last question as we wrap things up. This has been a really fun conversation, Daniel. Uh, lots of good stuff, um, that I have learned and just fun talking with you. Uh, what do you kind of see? Um, well actually let's, let's ask what is, what have you learned as a leader about yourself, uh, during this time? Uh, you know, there were some things that I did and haven't done that I wish I would have done and, and need to do as a leader. What are some things that you've done well, maybe haven't done well and learned about yourself during this time?

Daniel (26:10)
Look, I always have places to improve my leadership and interpersonal skills. Everybody does. I think the one thing that stands out for me is taking the time, uh, in a meeting, in a conversation, in a team, to really check in with people and make sure that they know that you care about them as people is enormously powerful. Uh, I would say in my prior lives, I've been impatient, you know, startup, entrepreneur and you know, you get on and you want to just get into it. Um, and certainly if you work in a big company where you're interacting, you know, it was like this at Salesforce, you get on a call, you don't even know these folks. You just like, let's get into it in what the coven situation has done is it makes it not only, uh, you don't just do the perfunctory, how you doing? You actually ask the question, right? I was with one of my colleagues yesterday who is a single person living in a small apartment in Manhattan, hasn't gone out in six weeks. Like that's gotta be crazy making and, and you know, I only had half an hour. I had to get some stuff done. But candidly, I spent most of the time talking to her about what she needed. We could schedule another call. You know what, that could be fine. We'll do that another time. Being more patient to make people feel comfortable and learn about them allows you to go faster later on because you know, that allows, uh, like my own rough spots when I'm maybe inpatient later to be forgiven because people understand where you're really coming from. So I think as a leader, that part has been really great and to be honest with you, I've loved it. You know, we have this thing at Shopify where you get a ping every week and it connects you with another random employee. Oh, of course. It's like, Hey, go have a coffee with this person. And for my first year at Shopify, I did it a few times, but you know, probably bad on me. I'm like, what am I doing? Like what is this about? And now I love, I actually want to request more of them because I learn about the company and I learned about my college career and about the people I work with just by hopping on for half an hour with no, like, I don't have an agenda with you. You're, you're working in a different team in the department. But I'm like, how did you get here? What's your story? What have you done? Um, and every single time I've come away thinking, I learned something about another great person, I learned something about this company. Um, and usually I think, damn, why wasn't I doing more of this sooner? Because it's really powerful. Um, so yeah. Anyways, like I said, I think that that, that, that learning about like taking care of people and taking a little bit more time, uh, to know their story, really make sure they're doing okay before you get into the work stuff is, is invaluable and, uh, a good lesson for me.

Joe: (28:28)
Definitely. Awesome. Well thanks Daniel for your parting words of wisdom. Uh, great talking with you. Good luck with the kids. Good luck with managing during this craziness and, uh, I hope to talk again soon.

Daniel: (28:45)

Thanks. Take care, Joe. Same to you. Good luck.



Joe: (29:07)
Thanks for joining the DNA of an Experience Podcast. We hope you learn something that will help improve your collaboration and enhance the experience you create for your customer. Join the collaboration 2.0 movement today by getting CloudApp. The instant business communication tool used to create instantly shareable videos, screenshots, and GiFs. Perfect for both internal and external communication. Get started for free@wwwdotgetcloudapp.com. Thank you. We look forward to seeing you next time.