Future of Work Series: Q&A with Des Traynor

At Vowel, we often chat with folks in our network (who also happen to be some of the most influential leaders and thinkers in tech) about where the future of work and collaboration is going. One day, we thought “Why not record it, and open up the conversation to be shared, right on Vowel?”

That’s exactly what we did, and that has turned into what you see here — welcome to Vowel’s Future of Work Series.

This is a conversation between our Head of Product, Anna Marie Clifton, and Des Traynor. Des is a Co-founder and the Chief Strategy Officer of Intercom and sits on Intercom's board of directors. Des has led many teams within the company, including Product, Marketing, Customer Support, and Content, and has been directly responsible for building out even more functions within Intercom as well.

Check out the conversation in full on Vowel or watch the video below.

Anna Marie: Well, hello. I would say good morning, but good, I want to say, afternoon, evening to you today, Des.

Des: Yes. Good 10 minutes past 4:00 PM. Yeah, exactly.

Anna Marie: 10 Minutes past 4:00. That's right. Okay. It's always hard to keep track with the different time zone changing and things like that. Well, welcome to Vowel's Future of Work Series. I'm so excited to have you here. Do you want to share a little bit about yourself and your background with our viewer-listeners?

Des: Sure. My name is Des Traynor. I am on all the socials as Des Traynor. I'm probably most known, or my entire career has been basically, I started a company with three friends 11 years ago called Intercom. It's gone on to be a big company now. We have like a thousand people, 25,000 customers, blah, blah, blah. And over the years, I've worked in most corners of that, but I'm most at home in product, and that's really where I've built most of my career.

Anna Marie: Now, you started Intercom across time zones. You had a team in Dublin and team in San Francisco. So, way back when, before working across time zones and all that was the hotness for startups.

Des: Yes.

Anna Marie: So, tell me a little bit about things that you learned early on, things that were hard then, things that we've kind of figured out now, maybe.

Des: Yeah. I don't know if it's definitely the hotness now, but I think the thing we had to come to terms with really quickly was, Eoghan, who was our CEO and is our CEO, he was in San Francisco. He moved over to raise money and start the company effectively in San Francisco, while myself and the other two stayed back in Dublin, Ciaran and David, and we were kind of building and managing the product, and I was doing blogging and all that sort of stuff as well, trying to get attention for the product. And very quickly, we learned that there's three hours of the day that are the most precious things in the world, the golden hours of 4:00 PM, 5:00 PM and 6:00 PM, and nothing that isn't really important should get scheduled during that period, because it's the only time when Dublin and San Francisco are relatively awake and relatively high energy. And this second part matters just as much, because we've all done, and of course in the early days we started, you can imagine I was doing 10:00 or 11:00 or midnight calls with Eoghan. The challenge there is, when you get really fatigued, any sort of decision making just degrades. So, understanding that there's a three hour burst every day, and we're in it right now, where important stuff can get discussed, debated, and preparing yourself for that meeting. You can't be phoning it in. I lived in San Francisco for three years, as well. You can't be stumbling into that meeting tired and gulping your coffee for the first 30 minutes, because important stuff is going to happen, and you need to be alert and able to argue or debate or agitate or communicate in that period. So, that was the first thing. I think the other thing that a lot of the listeners will be now familiar with is just waking up in Dublin to an onslaught of what happened yesterday in San Francisco, and the whole temptation, if you're in Europe, to work all the way through the night's pretty high, because SF's still awake. And then, the SF version's slightly different in that at 5:00 PM in SF, most of the Internet's asleep. Dublin's... Australia's not really active yet, and Europe's gone. So, you kind of have this proper evening. However, the worst part of waking up in San Francisco is like, nine million mails from all of your colleagues in Europe telling you all about all the shit that's been going wrong, and the chance of you waking up to an outage or a crisis of any sort is higher, as well. So, I think we just have to prematurely develop a lot of muscles for these things. Making sure that you've got an adequate amount of decision makers in all of the different time zones that you want to cover. That trickles into things like customer support and escalations, outages and all that sort of stuff. And then, I think the tooling on how you have to make decisions in the absence of everybody. You really need to, it can't just be like, "Oh you missed a meeting, sorry about that. We're actually not building that product." Even if the three people whose most skin in the game are in the room together and they make the decision, you have to assume somebody somewhere else in the company needs to know, but also needs to know why, because otherwise it can feel pretty much decisions handed down from on high.

Anna Marie: Totally. Yeah.

Des: So, if you wake up in Dublin to a decision made in San Francisco, it can feel disempowering at times, unless it comes with, "Here's what we talked about and here's how we got there." And then, most of the time, then you're looking for like, yeah, okay, they had the weighing scales right. They had all the right stuff from both sides and they made a call. No problem. And vice versa. In San Francisco you often wake up to things, "They built what, now?" And again, it has to be okay, as long as you understand it. But there is an obligation, that honestly has kind of helped us transition into being hybrid, or the period where we're full remote in the depths of Corona, which is the muscle of just documented decision making. It's important, basically.

Anna Marie: Totally. Absolutely. That's one thing that I've really been loving about Vowel, that we're scattered across nine different time zones, and so one thing that I really love about making decisions at Vowel is when you need people who are across time zones to be in the loop, maybe they can't necessarily be in the meeting, we have a habit of inviting them to the meeting as optional so that they have access to the recording and transcript and notes. And so, there's always an easy way to catch up on 2X speed, or just letting us look at the notes for what the decision was, click right to that timestamp and see, when they wrote down this is the decision, what were they saying?

Des: Yes, exactly.

Anna Marie: So, you can get that context. Because the nuance, the human nuance, you can feel so out of the loop. You can feel like, well, why did it... what are those nimrods doing? And then, you're in the call or you're watching the call, and it's like, oh they had a lot of nuance in how they approached that decision, and it can definitely do a lot to assuage any ruffled feathers.

Des: I'm curious. This is a Vowel question, on the Vowel product and the company. Do you have a specific syntax that you follow when you make a decision in a meeting? Let's say you and me decide, hey, we must totally grab coffee next time in San Francisco. Do you write the word decision in all caps, or is there a feature where you record the decision? How does that work?

Anna Marie: Decision as a feature is one of the things I'm most excited about getting into. But with product people, you're always excited about the next innovative fun, fun, fun feature, when it's like, actually we need to eat our vegetables and put in all the little things here and there. So, in terms of our future innovation, that's where I'm so excited. But for syntax here, we just will do a quick heading and just put decisions.

Des: And that's enough to search. As long as everyone has the discipline for doing it, then it's fine.

Anna Marie: Totally. Absolutely. And then you just search. The other thing is with Vowel, search across transcripts and all that, you just search a keyword and you go to where someone was talking about, okay, we're talking about multi-region support, so what was the decision? I'll just look up multi-region and click the transcripts and see the five times we mentioned that. And so, it's pretty interesting. It's also, yeah, I mean, there's a lot of things there about how you search information that I found really fascinating at Vowel, because as you think about search getting good at Google, there's so much powering the nuance of, okay, where was the person when they typed that search, and how likely were they to be looking for this versus that? And all these other things, that you really don't have to do when you're all working in the same environment, and when you're storing the information, the way humans index information. Because when I'm thinking about what someone said, or if I said something, or things like that, I'm usually thinking about who I said it to, or who else heard it.

Des: Yeah, who was in the room.

Anna Marie: It's always indexed by person. And so, Vowel search is all indexed by person. So, you search a term, and then any other person that was in the room, and it really quickly isolates down to that conversation.

Des: Right, it's so essential.

Anna Marie: But I definitely, this is something that, I mean, I've been thinking about decision documentation for years, since we had our first conversation about that, I think, talking about how easy it's to get lost in Slack, and there's just no decision product out there that really documents and keeps that. So, yeah.

Des: I mean, since we talked, I remember Atlassian, I think, released some sort of, if you're all in on the full of suite, you can search through a decision made in any product, whether it's Jira or Confluence, whatever. And I'm sure that works for some folks. But in general, I just think decisions are, if you think about when people talk about, say, the office suite, they talk about the primitives being a doc or a slide or a spreadsheet or a canvas now, with Miro or Figma or whatever. I actually, that's a very back to front way to think about it. The actual things the companies trade off are decisions, input, output, metrics, things like that. I think it's the single hardest thing, when you join a company, or if you take a week off, or even honestly if you wake up in the wrong time zone, is to work out, what did you guys decide to do and why?

Anna Marie: Yeah, totally.

Des: And oftentimes, people are disciplined enough to share an email after a meeting or whatever, but if you think of all the extra work-work, all the junk that has to happen, which is like, I'm really glad that Des and Anna Marie have come to a conclusion on X. Now, the fact that we have a decision means that we have now seven other problems, which is internal comms, and sharing this build. And there's no ambient way to say, this is now decided. I do think some sort of central decision plus context registry would actually speed a company up quite a bit.

Anna Marie: Totally. One of the things that we get as a velocity accelerant is, you can make a clip out of any part of a meeting, but you can do that in real time. So, right now I could be like, you know what, that's a really good point. I'm going to put that in our product ideas. And you go right in the transcript and make a clip and send it while we're talking to a relevant person. And so, the number of times I've been like, oh man, our customer success manager really should know this information, and instead of scheduling a meeting or remembering, I just, in that moment, I take 30 seconds to send them that content. It saves so much time, and also, so much lost context of how often are you going to forget that you meant to send that, or you meant to talk to that person? It's so incredible. And then also, how often do you forget yourself what you decided?

Des: Oh, yeah.

Anna Marie: It's like, you pick a project back up three weeks later and you're like, oh, I know we had some tricky edge case, and I don't remember what we thought we were going to do about it, but I remember we decided. So, just being able to navigate back to those has just been pure gold. I feel like when I'm not working at Vowel now, like on my side projects, I feel like my brain is actually slower, and my ability to collaborate across groups of people feels a little bit like... Because I'm like, we talked about that, but I have no access to that information.

Des: It's one of the reasons I was excited to invest in Vowel was just, I realized that genuinely, when any meeting happens, it's usually to make a decision, but occasionally with a status update. But it's usually a decision, even if the decision is just, should we keep going? And then, the problem of the decision is, it does need documentation and context, and then there's implications of the decision, which is the sharing part. And with the right tooling, all of that stuff is taken care of in seconds, and with the wrong tooling, every single one of those things is a task for some program or project or product manager to go and do. And that piece is just, it creates so much work-work on a decision that they become quite expensive. The other side is, even if something is just a context only, like FYI, here's the latest on blah. For sure, I know the folks at Loom would argue, hey, we should just send the Loom Clipper in, or whatever. And that half works, but oftentimes people actually want be live in the context to ask the questions, as well. And again, those status updates, while useful, you'd never have a 100-person meeting, but you may well have 100 people interested in how a certain project is going. And there's no real need, there's no real reason why you shouldn't be able to share, hey, here's the four second snip where we actually discussed that, and here's what we got to. When I think about all the hijinks we'd have to go to do this with Google Meet or whatever, it'd be shocking.

Anna Marie: Yeah, yeah, yeah. Well, I'm curious a little bit about how you think about Intercom enabling and empowering the hybrid workplaces. Not just being one, but the product side of that.

Des: I think, at the start of this year, we released a major rebuild of our inbox, and one of the core ingredients, at Intercom we have this thesis of next generation software, the idea being like that back in the day, when me and you had started our careers, next gen meant if you could something in a B2B SaaS app, that was mind blowing, right? And that was actually breakthrough shit in 2012, right?

Anna Marie: Yeah.

Des: These days, what's breakthrough, I think, is products being multiplayer, AI, ML, keyboard first, dark mode. Just, when you pick up a product, say Linear or something like that, you're like yep, everything here makes sense, right?

Anna Marie: Yeah.

Des: And I think multiplayer is a huge piece of that, which is the idea that if somebody else is using a product at the same time as you, it's a lot better if you know it. I think the kings of this for a while were Figma, when they had you see all the... Or Miro, for that matter. And then, obviously, you could talk while you're in the same tab or whatever. We took inspiration from that idea of multiplayer, and what would multiplayer support look like. And I don't just mean in the sense of assigning conversations back and forth. That's a very old school multiplayer, like, hey there's more than more person here. But I mean, modern day multiplayer is actually, John is also looking at this ticket right now, and you can have a conversation behind the scenes with John. I think all of that kind of makes a lot more sense in a hybrid world, because it used to be the case that support orgs, especially because support orgs would typically have been co-located for quite a while. So, it used the case that someone could just lean over your screen and be like, "Oh, here's what you should say to that person."

Anna Marie: Right.

Des: There's no leaning, there's no screen. All that stuff's gone. So, when we talked about how would Intercom better enable hybrid, well, the first thing you have to do is be a tool that is better for remote work, and not a tool it isn't, right? And so, we built a lot of features into our rebuild and relaunch, which we launched in March, and it's been widely appreciated. In general, I think we've just seen the request for features along those lines. So, another part of the Intercom, say, is marketing. So, we have a series tool for planning outbound messages to get people to use the new feature, or whatever. We see a lot of requests for, hey, I'd really to be able to leave a post-it note on this screen that explains what I'm trying to do, and if I can mention somebody, they'll get notifications. So, we started building all that, too. You can literally put sticky notes over your series to annotate it and stuff, because we realized, it gets close to being a virtual whiteboard of sorts, except for it's one that's attached to marketing campaigns. In general, I just think most software in a hybrid world, you have to assume... The good of this is, you have to assume most things that happen in your product matter to somebody other than the person who did it. So, I've logged in expense. The accountant needs to know, or whatever. And you have to assume now that the products that will win are the ones that don't mean you then have to go and copy the URL, flick to Slack, find the person's name, send them the message, say, "Hey, I just logged it." You have to effectively take all of that work-work away and make it so that everything that happens happens in the right context, including automatically notifying the people who need to know. Now in general, the mantra of B2B SaaS for me is always, whenever something is done, the PM has to ask themselves, now that that file is uploaded, appointment is created, mail is sent, whatever it is, who needs to know, and what would they want to do about it next? So, sometimes Anna Marie has launched a new project. Do you want to give it feedback? Or Des has kicked off a new expense. Do you want to review it? But understanding that level of collaboration, and understanding it not just in the async, sort ping everyone in an email or Slack. That's useful, and a lot of people don't even get that far. But then, understanding it in the actual raw multiplayer, like what if two people are doing something at the same time? We get requests for our email editor to be multiplayer, and that would be a phenomenal amount of work, but we may have to do it. We'd rather not, but you can imagine, people want a Google Docs style interface to everything now, and that might be the case. Even, you can see it here in our right hand column here, we've shared notes where we can both type at the same time.

Anna Marie: Totally. Yeah, we think a lot about that. It's interesting, because the language of multiplayer is not one that I've really applied very much in my recent work, but it kind of hits on the thing that we've been talking about a lot, which is just the transition from work to being something that happens here to being something that happens mediated through a digital interface. And I mean, my personal thesis on humanity is that we're well past the point of time at which great things were done by individuals, and now we're into great things being done by great groups of people. And so, that intermediary between people being all digital now, because you can assume that almost always people are going to be working across time zones or across locations now. There's always going to be some other office, some remote employee. Even if you're entirely in office, you've got work from home days now. And so, that just gives more impetus, but also more opportunity in the software side, because there's so much that's possible when you have a digital interface. Like we think with meetings, it used to be that after a meeting you relied exclusively on the best note taker for what happened in that meeting, right? And then, now there's this huge, huge opportunity where humans are really bad at remembering things. It's one of our worst skills, right? And computers are just amazing at remembering things. It's what they're best at. And so, it's a great opportunity to trade off and be like, okay, computer, you do the remembering for me, and I'll do the work. And that's something that's just a really, really beautiful way to think about that in conjunction with multiplayer. It's just, what does it mean that we have this digital intermediary all the time?

Des: Yeah, totally. The other thing I often think about is how GPT will kind of augment and build bridges for us. When it relates to things like searching, there's a lot of people who have built really cool products that all they simply do is say, I know you're searching for that word, but that's not the word you mean at all. Were you asking about this? And if you think about us replaying this conversation, if I went home tonight and had to relay to somebody else, what did you talk to Anna Marie about? I'll probably end up trying to recap everything you said, but I won't use the words that come naturally to you. I'll use the words come naturally to me. Whereas, and that totally destroys the traditional search engine, and we see this happen all the time. So as a result, you ever have that problem where you're searching Google Docs, you're like, where the hell is it? Oh, you called it a setting, not a preference.

Anna Marie: Right, exactly.

Des: That sort of thing. So I think, as we get to augmenting our brain in loads of different ways, and being able to interpret and reinterpret things so that they can be easier to find, or easier to construct, I think the entire collaboration world will change.

Anna Marie: Oh, I love that. Well, I want to be mindful of time, here. I know we've got to hop, but you just had a big launch recently, so I'm curious if there's anything you're kind of excited about, or just any keynotes from that that you want to share?

Des: Yeah, thank you for asking. I think the single biggest thing, so the Intercom messenger is the thing that we're known and loved for, you see everywhere, widely copied and never surpassed. Yeah. We released a brand new messenger internally. It's our, I think, fifth generation of messenger, but we added a phenomenal amount of customization. The whole underlying thesis was, this is not our messenger, this is your messenger. So, Vowel can have it in its perfect purple with the perfect V logo and all that sort of stuff. It's got new features in it. You can do checklists, so when people are onboarding, you can set certain goals. It has a news feature, so you can update people about anything like product releases or company updates or anything like that. There's a lot in Messenger, honestly, but customization is the thing. You're going to stop recognizing the intercom messenger, because it's just going to look like every company has its own beautiful messenger, and that's exactly what we wanted to get to. The other huge release was ticketing. For the longest time, Intercom was a support product. Without doubt, our biggest request was, we want classical, old school ticketing. And we'd always been kind of somewhat reserved to do it, because we didn't like the idea of treating customers like tickets. But we found a middle ground we were happy, which is conversational ticketing. So, it works all the ways you expect tickets would, but it also lives in the messenger too, and it has all of the sort standard features you'd want in a ticketing solution. And we think that just really opens up the platform for people to switch to wholesale Intercom as a support platform, which they're doing. There was three other smaller releases that we don't have time to get into. They're most mostly on the engaged side of the house and our bot builder, as well. But yeah, it was a phenomenal day. It was like, it's cool to do those hybrid online/offline events and see how many people were blown away about what we built.

Anna Marie: Totally. Well, I'm really excited to integrate some of those things, especially on the tech list side. So, really excited to see some of that. I'm glad you're at the point of your kind of company maturity where your brand doesn't... it stands on its own, and you don't need it to be in the little dot there at the bottom.

Des: Yeah. It will still say that we run on Intercom, but the dot's a different thing.

Anna Marie: Awesome. Well, thanks so much for your time today, Des. It was so much fun, as always, catching up. Chat soon.

Des: Chat soon. Take care, Anna Marie. 

Where to find Des:

• Intercom: https://www.intercom.com/

• LinkedIn: https://www.linkedin.com/in/destraynor

• Twitter: @destraynor

• Website: https://destraynor.com/