(25) E41: Jessica Chiew of Canva on Building AI-Native GTM Org - YouTube https://www.youtube.com/watch?v=wI3FzuZFC20

Transcript: (00:07) Hello and welcome to the revenue leadership podcast by Topline. I'm your host Kyle Norton, CRO at owner.com and every Wednesday we dive deep into the strategies and tactics being used to drive success by the best revenue leaders in the world. (00:29) So, join me as I sit down with revenue operators to discuss actionable frameworks that you can implement in your business today with no fluff, no sales pitches, and no platitudes. This episode is brought to you by Pavlov. I'm excited about this one because as a customer myself, I can tell you it's a game changer for revenue. (00:49) We all know acquisition is critical, but how much revenue opportunity are you missing post sale? Pavlov's AI agents plug directly into your entire GTM stack to find opportunities and take actions that grow revenue from your existing customers. Whether it's accelerating time to value, driving expansion, or proactively addressing turn risks. (01:07) For us, Pavlov cut our customer time to value in half and increased our revenue activation from 70% to 90% plus. This product is insane. Learn how Pavlov can accelerate your NRR growth at trypav.com/kyle. That's t r y p a v l ov.com/kyle. Today's guest is Jessica Chu who runs GTM Operations and Strategy at Canva. I'm sure everybody listening knows Canva. (01:36) They're 5,000 person organization today. Over three billion in revenue and uh shockingly 220 million monthly active users. Uh which I had to double check with Jessica because I couldn't believe it when I heard it. Uh, prior to Canva, Jessica was the global head of revenue strategy and analytics at Auna. She was a GM at Spruths Health. (01:59) She came from a consulting career uh at McKenzie prior to that. And I'm really excited for this one. I keep getting drawn into AI conversations whether or not I try to or not. And uh uh I've followed along with some of what Canva is doing and and a little bit of your uh content along the way. So I'm really excited for this one and thank you for joining. Thank you for having me. I can't wait to have a great chat today. Yeah. (02:26) So uh the topic is GTM AI transformation. It is the topic by far that I get asked about the most from other CRO from people that uh want me to speak at events or like founders reaching out. it is the the topic dour and I'm trying not to make the podcast only GTMAI although it's quickly becoming that u so there's clearly like such an intense anxiety urgency uh and interest in the market and so I'm hoping today we can give people some first principles from which to work from to think about okay I'm a traditional uh series A to D or E (03:07) SAS company And I know that this is a transformative technology, but like where the heck do I start? Um, and we'll get into how Canva's done it and and some of where you think the market's going. Yeah. Um, so that's the framing of the conversation. Uh, my warm-up question though, is this the most fun you've ever had as a as an ops leader? This period of time we're in right now? It's so much fun. (03:38) I uh sometimes I say this to my team um and it's a little it's a little cheeky. It's not really what I believe, but sometimes like ops and especially sales ops is kind of the same problems over and over again just in different contexts. But I think this is the first time that we've actually had a chance to be super creative and build like almost like product owners and think about how to change how we're building sales or for the first time in like at least the last 5 to 10 years I think. (04:04) So, um, having a good one, being really creative, it's like kind of a muscle we, um, I personally haven't felt I've stretched in the last few years, but have been in that mode, at least the last year. So, yeah. Yeah. Yeah. I felt a little bit like this when the sales engagement boom first happened in sort of like 2014, 2015, but nothing like this. (04:27) Nothing with this, you know, scale of transformation and this size of opportunity. And and the funny thing is this is definitely the most fun I've had in in my career. AI has a lot to do with it. But then I also have this like constant existential dread that I'm not doing enough. I'm not moving fast enough. I see something that Clay is doing. (04:46) I I chatted with their CRO a couple weeks ago. I was like, "Oh my god, we need to go faster." So the combination of thread, I think it's tough. I think um you know, I've been really curious and creative on this stuff and the team's been doing a lot. (05:05) when you speak to other peers and other leaders in the space, I think you realize that um not everyone is is like navigating this in a way that feels constructive. People are nervous. It's really hard to figure out. So, I'm excited to to dig in. Um but yeah, I agree. I think 2014 15 like great new tools came out like when call recording and like outreach automation and instant booking stuff like oh that was that felt like a bit of a burst. But even for me like I would say over the last three four years my vendors will hate me. (05:30) I've not leaned into vendor conversations because you know I haven't found like it's it's like a lot of tools have been commoditized been so much consolidation like people haven't been bringing really exciting stuff but that's all changed like in the last six months I've had to I'm leaning in. (05:47) I'm speaking to early stage I'm I'm speaking to all my existing vendors and like being really open to hear what folks are building because it's changing so fast. Yeah. How many demos a week do you take right now? Oh. I'd say like two demos but then also just like meeting with earlier stage companies to see what they're looking at because some of the folks that are emerging out there that might be two three people like they're not reaching me but um other companies that are much smaller than Canva are looking at them and so I learn a lot by speaking to earlier stage peers to be honest as well. So kind of demos by proxy. (06:17) Okay. Yeah, that's that's similar to me. Like two anywhere between two and four because we're I feel like we have a plan and I know the next few building blocks, but it changes so fast and and um I feel like I just need to stay with finger on the pulse. Yeah. So, absolutely. (06:39) Um okay, so we're going to break this conversation up into roughly four parts. I I I really want people to walk away with a strategic framework to start like how to think about where you should start with this transformation. I have particular opinions on it and so uh I'm going to bounce a couple of those off you and then uh once we can give people a strategic framework we'd love to I'd love to talk about uh use case prioritization specifically where in the stack can people start then we'll talk change management and maybe if we have time talk personal productivity uh but but (07:09) we'll see. So you joined uh almost two years ago correct? Yeah, correct. Yeah. And so post chat GPT moment but but at the very early innings of these starting to that AI transformation coming into GTM tooling. How much momentum was there around AI in go to market when you started? Yeah, I think um it was starting. (07:38) So I think we were just coming off as you said like everyone adopting chat GBT. I remember like two and a half three years ago when I was at Asana we had this huge I remember had this huge AI push um and we had like some BDRs pioneering these very detailed like creation of research agents speaking to prospecting copywriting agents and like demoing their workflow. It was like you could see the code being written. (08:02) It was like a 15-inute process and boom you have like maybe one email, right? um than anything anyone had written. But I think we were still kind of at that moment where that felt like really exciting but still pretty heavy. And maybe I would say fast forward to a year ago, so 18 months after that initial point, okay, now we have vendors where like that entire workflow is like you click a tab, you push a button and you've got not only that but contact source, the first three emails drafted. (08:32) So, but reflecting on when I joined Canva, I it was still an excitement phase for me, but I and I don't think but I don't think that we had the clarity that has been building over the last six to nine months. So I think walking into Canva at least I had the benefit of Canva being very much like an AI native AI first company both on the product development side like we I think we've been really early to the AI game even prior to all all the momentum the last few years in terms of building AI features and being that philosophy but more (09:02) importantly I think as a company like AI first has been part of our culture to the point that like I use the example like we um in our you know half yearly performance reviews. Our founders added a question over a year ago at this stage which was like how are you using air in your workflow? So I've had the luxury of being in a company where you know that is part of the founders philosophy lead philosophy like forefront and everyone has access to all the tools that they want right so um I think I think the appetite was there in terms of (09:33) like how is it transforming my job our go to market org like it was really early days two years ago in a really different spot now over the last six months and and there's a range of uh I think like adoption interest. There's companies like ours that are just like allin from CEO down. It's clearly the future, but then some companies that are a little slower on the move for for whatever reason. (10:01) Uh when you talk to folks like that, so revops leaders or revenue leaders and companies that don't have that same uh don't have that same support, what advice are you giving them? It's a great question. I mean, one, I think it's really hard if you don't have companywide backing that this is important. (10:22) Um, and so for me, it's like you've got a role model that like, you know, with your teams, like that's how you run your team. That's how we approach market ops. But I think it's like practically really diff like difficult because we've been on this journey as well, right? There's one thing to say, hey, in everything that we're do, we're looking for ways that AI can augment or improve existing workflows, but at the same time like everyone has a day job. uh and everyone has lights on. (10:46) So you're trying to ask folks to carve out 10% of everyone's day to do this and um we should trade notes. But like my big learning is even the most basic workflows take iteration when it comes to uh we can talk sound simple demo really well. When you get into the nitty-gritty it's like oh there's actually like 20 different design decisions and implementation steps to get this right and get this at a point that you're really excited about. And so it's really hard I think when you're asking for like 10% of everyone's day. So the advice I give is (11:18) like our learning has been that the first step is to you have to tell people this is now part of their job and they have to take there and they have to be experimenting and exploring. It's everyone's it's part of everyone's JD. But we were on this journey and it was interesting. (11:34) We had a call with a vendor where they showed like the potential and I had this aha moment maybe like six months ago where I was like shoot we need like someone dedicated on this. Um, and so I called someone on my team who was working on another program and I was like, I think we need to change your job like tomorrow and I'll give you the on it, but do you want to move into a dedicated AI role? And luckily for me, that person is awesome and was also excited. (11:59) And I can see the difference in like how much faster we've been able to move with folks that are dedicated. And I see I see it on at least on LinkedIn as well around people starting to move people into these dedicated roles. Um, yeah. So, what's that role called for you? We call it our He is our go to market AI lead. Okay, that's funny. (12:16) That's the same title we we've used. Yeah, there you go. There you go. Um I know like you know folks like Clay, you've got go to market engineers and and all that type of stuff. It's it's getting its own branding, but for me it's interesting. I'd love to trade notes on how you've hired and what you've hired for, but it has to be this person who is a combination of um kind of like a product manager, deep understanding of sales workflows and then able to drive and project manage like a cross functional technical um process really every time you stamp out (12:46) one of these workflows. Yeah. our our so our setup is interesting and and we'll talk about this when we get into more when we get into like where to start but I think um there's a data layer that is the most important part of any of these transformations and so there's actually a lot of this job there's a lot of these jobs to be done that actually for us live in data ops we have a really strong uh VP of bisops and data um he has teams of data scientists and data engineers that are working on the underlying foundation for a bunch of this and so and there's a lot of people (13:29) in the GTM engineer category that have that job that really do that. They're like I'm a clayt expert. I'm doing all the enrichments and the waterflow stuff or waterfall stuff. Uh but that for us actually just lives in the data team and we're solving it there. And so for me, the GTMAI lead is is finding ways to go uh improve the workflows and tooling and like solving problems. (14:02) So an example is just like when there is a when there's no tool that exists, are you going to vibe code an internal app? Are you going to just build like an extravagant clay table that answers this thing? Is it, you know, are we just like teaching people to MCP and to the like the different things we already have and we need to give them a a prompt template library? Yeah, that's sort of the GTMA I lead for. (14:21) We're in the same place. Yeah. To me, the work we're doing with Clay, we're also customers and enrichment. That's to me the new way that sales offers their most basic world, right? Which is making sure our CRM is up to date and accurate and enriched. (14:38) Um, our go to market AI work is all about those workflows that sit on top of the the data layer. Yeah. Yeah. I was asked by a company yesterday a similar question. They're like, well, you know, like we've got some data people in RevOps that do this stuff and then we've got data people that are associated with product and so how do you reconcile this? And I my advice to them was it's got to be centralized. Like I don't know. (15:00) I think in this AI world where data being clean and centralized and um having consistent access points it like just needs to live in one function and and we have dedicated people in data. There's there's data people that are dedicated to GTM and to product but it's but it's centrally managed. (15:24) Is is that similar for you guys? Yeah, we have a central data team. That's our setup as well. But yeah, you rais a really good point which is um it's interesting. It's interesting with Clay, right? Like we used to have a central data team who had ma built and managed their own waterfall and now you've got a vendor who is like it's a waterfall out of a box. (15:42) And so we've had to also rethink like when you don't need data engineers maintaining this infrastructure or how do you have folks who are not just maintaining the waterfall logic and plugging in all the old vendors like we can uple the data resources we have as well to getting to the next level on data I'll give you some really great examples but it's part of this transition of like engineer to analyst profile right so previously it was like okay we have all these people maintaining a basic waterfall and at the end of the day like (16:11) I'll give an example verticalized sales teams and slicing and dicing by industry. we could only rep like rely on the structured fields and tags that are clear a bit zoom info kind of yeah yeah yeah well it only gets you so far right there are weird edge cases and so now we're able to like plug that stuff into clay and say all right regardless of what the structured fields say but these accounts it looks a little blurry let's go and like look at their websites and this is the spirit of how like what we define as an industry and come back and tell us (16:40) whether you agree or disagree with it and so I think the skill set for that type of inquiry that requires a lot more business context and understanding of like what we're trying to achieve with enrichment is a different profile to the folks who are like maintaining the integration data engineers. Yeah, data engineers. (16:57) And so I think that's something that we're working through as well, which is how do we get on the data side people much closer to the business intent because that's how you can get the most out of these tools, right? Yeah. Yeah. That's interesting. That's similar to the profile that we're putting into uh into that function. (17:15) We're looking for for folks that like for our uh data scientists who will be uh aligned to the business units. Yeah. We want somebody who went to did a computer science degree but then worked in consulting like was a Mackenzie consultant and then has spent a couple years in the tech company. (17:34) That's like our perfect profile because they they have the combination of business context, technical capabilities, and they can solve things either within Clay, you know, faster and easier because that's a platform or outside of it if there's like weird edge cases that we need to build ourselves. That's a tricky one. (17:55) Um, okay, let me let me go back because I knew I would go get in the weeds instantaneously. So uh how is the company approaching this transformation uh from from like a high level? Are you guys doing a bunch of bottoms up experimentation in these different business units? Is there like an AI council like what where where is the transformation being driven from? It's a great question. (18:21) I think the model we've taken which is being kind of you know sponsored and designed by our founding founders and leadership is um we do have like a centralized AI council I don't know what we exactly call it um uh that is sits within our IT organization and their mandate and job is they've staffed up with like cross functional folks of engineers technical engineers our security privacy team um uh and they are empower they they are resourced to empower the functions with whatever AI initiatives they want to deliver. So um there's no excuse for lack of like company level support and (18:57) um staffing to get new vendors on board to build out workflows and drive cross functional alignment. But I do think a lot of the power has been put back on the functions to bring to the table like what their ideas and programs are. So it's this combination of like yeah company level AI council with empowering functions. (19:22) I do think that like functions are at different stages and go to market is typically ahead right because yeah yeah I think that's where a lot of vendor action is happening in addition to customer support and that other type of thing that's the model we've taken. Okay. And so where do you uh where did you start and where do you advise people to start when there's like hundreds of use cases all of these vendors? Yes. You could start with like upskilling people to use tools. (19:47) It could be about picking tools like you can be like oh just start with the data. Where where how do you think that people should approach the problem? It's a great question. I mean, it's pretty maybe before I give you our approach, I just want to acknowledge it's pretty overwhelming, right? Because AI, quote unquote, AI is coming from so many different directions. (20:05) You've got individual folks on the ground pioneering their own workflows and using tools. You've got your existing vendor stack coming to you every week with the new feature AI feature they've built, their rebrand as an AI company. You've got new vendors emerging who are saying, "We know how to do this point solution really, really well. (20:24) " And then you just have like company leadership saying hey this is a priority like show us your plans and so yeah it's coming from every direction. We've been on a journey I would say and this will land at like the approach I'd recommend. I think it started with like individual contributors or bringing their best ideas largely out of like hack together GPT prompts. (20:48) M um then we spent a then we spent a chapter looking and working with our existing vendor stack to say who's got what what are we excited about and then we ended up in a more kind of um organic space which was like where what are the jobs to be done the workflows that we feel like have the biggest opportunities um and how do we want to solve those and I think my advice would be the quicker you can cut through the first two steps and get through that noise and just landing it at like for our business like what are the biggest blockers and pain points. Um where are the bottlenecks in (21:20) our business? Okay, then look at the landscape to say what are existing vendors offer, what are new vendors offer, what what can we pioneer and innovate ourselves and where do we need to build and actually build out like data engineering resources to build inhouse. That's kind of where we've landed, which was start with the jobs to be done and then, you know, kind of like map map how you want to solve it across the many different ways you can solve it. So that's where we've landed at. And so for us, I'll give you some examples like (21:49) um quality prospecting, hyperpersonalization, it's what's on everyone's mind. Like we know that that's a gap for us. And so we've started there and then we've gone through the whole exercise of like okay do I have existing vendors kind of do that well or is we have to bring someone new on or is there stuff we can build ourselves and for that one as a tactical example we brought in a new vendor to help us with that. (22:11) Well that's kind of been the approach we've taken is we've like it's like a slide on the left hand side it's like what our priority jobs to be done that we think are going to move the business regardless of you know who's got what and then just keeping an eye on like all the innovation coming from every direction. You kind of just make some bets. (22:28) Yeah, the the advice I find myself giving the most in sort of reflection of where we've gotten to is companies should start with the data in and like if you don't have really high quality data about your market about the accounts about the people and then contact data to actually get in touch mobile phone numbers in particular a lot of other stuff isn't going to work because you know this is AI is a pattern recognition and a replication engine. (22:56) So if the underlying data is not good, then then you can't understand what a best fit customer looks like or or forecast properly. So I I keep telling people I think go solve the third party data problem and then the first party data problem which is if your product data isn't doesn't touch your prospecting data or your sales reps aren't really filling out CRM fields properly then again like you don't you don't really have the the basics to then um build hyperpersonalization because you know if only some of the context of the prospect and what's happening across (23:35) Yeah. How can you how can you do how can you put that into like an ML model and and have it make much sense of it? What's your reaction to that? Like this is becoming more of an opinion and so I keep stress testing that but like I no I I would really agree with that. (23:54) I think there's a lot I take for granted coming from largely a PLG background with both Canva and Asana in that a lot of the first party stuff that you piece together to me is kind of inherent to the motion and something that we've always invested in. But you're absolutely right, like enrichment is one piece and just like that, you know, bread and butter stuff and then piecing together the full 360. (24:15) I hate the overuse of the word, the customer 360, but really the 360 of um all of your marketing interactions or your product interactions and then all your sales interactions as well. That is the fuel to, you know, things like personalization, things like prioritization and really changing and transforming some of the ways that our reps spend their time. (24:32) So, no, absolutely agree. But I think there's a piece of that that I have been in the luxurious position of taking for granted to be honest that yeah yeah it is definitely not not the not the norm like most of the conversations I have with folks this is this is what I ask and they're like oh yeah you know I was like what's what's the quality of sales reps filling out fields and is your salesforce getting worse over time or is it getting better and they're like well like worse because you know the the things aren't updated (25:02) And then you know we don't know and so the I generally I'm like go just use momentum that's that's what we use for CR we like I I'd love to hear your experience on getting to your partnership with momentum but I made it I've been on a journey like we we've got a big project called CRM autofield which is basically what what you said I stood up at our um sales kickoff at the start of the year and I promised the sales team I was like we will never add another pick list to Salesforce making you tell me loss reasons or competitors we know that we make them mandatory and (25:33) it's junk information and before every QBR we're like manually taking our top 20 deals and filling it out anyway. Um, but we've been on a real journey with that cuz I think I had an aha moment. I'm going to figure out like September last year I was like we should be able to do this better. (25:49) Um, and then you hear about a few vendors like Momentum and others and and we took some vendor calls and just as like a practical reality, I was like one, I was like shocked at the price tag of some of these companies that didn't have proven customers yet. Two, I was like, "Okay, got a 3-month procurement process to get this through cynically. (26:11) " And I've got scar scar tissue around adopting earlier stage technologies and partnering with early stage vendors because we've got a big business to be running and we're at the scale now where I can't I can't kind of run the risk of folks not sticking around or their product direction changing. (26:31) And so we went on a bit of a what felt like a wild goose chase where it's it's all these highs and lows of like AI um iteration. But I found an ML engineer at Canva and we basically like oh we're going to build it was like a queryable gong like database we're on was like this is a gong rag essentially we can build a structured table about all these things that we never have to ask reps for again and I think one big learning that I you love your take on is like so easy to prototype in AI really oh man oh yeah we had this moment of glory hence my big statement at the at SKO which was like (27:04) we're never going to make you do that again. This thing was like so fantastic. We could turn around iterations so fast, but then it was like slow. It didn't really get the answers right. And so fast forward to that was in December and fast forward to now July. (27:22) Like we've finally tuned it and it's finally working and we now have built this like in-house platform as opposed to going with vendor that we've got like the product team is like building their own insights out of this structured all calls, right? we're going to be able to go and now we're just picking like what fields we actually want to push back to Salesforce. (27:41) Do we even have to push them back to Salesforce because we have this snowflake table that we can add structure at any point. So, it's now this amazing moment of glory, but it's been a nine months journey and um in in hindsight, I was like, should I have just gone with a vendor? But it's really hard to figure out like just with the pace of things, you know, and how how things how fast things are moving, like what's the right investments to make, who do you partner with, and what are the benefits of being able to own this stuff yourself as well? Yeah, we wrestle with that same thing. (28:07) And and so we're we're careful with who we who we bet on. I think about those early stage because I think I was one of Momentum's first three or five customers or something. And so it's really I I think about it the same way I think about writing an angel check. Are we directionally aligned on solving this problem in the same way? Because if if we have the same philosophy on on how this problem should be solved, then I think you'll iterate in the same direction as I would as I would want to go because I've been there where you (28:40) have an exciting pilot and then you're you're with a vendor and and they go someplace completely different. You're like, "Oh my god, this is not what I signed up for." Yeah. And so it's about are we philosophically aligned? And then do I think these founders can win? Yes. Because that's that's the other that's the other piece of it. (28:57) If the if that founder can't win, then the product won't get better all that fast because they don't have enough traction. They can't hire the engineers. And you're really you're really trying to uh buy a tool that you think will be way way better in 12 months, especially in the AI world. Like there's a there's a bunch of implementations like we use Avara as this sales simulator and the first version of that was pretty janky. It was it was like really cool. (29:26) It was a great It was a really impressive pilot and prototype and a super impressive team. I'm like, "This team will figure out how to make it better and better." And sure enough, like three or six months goes on and it's it's great. And now I have the advantage of being I like partnering early. (29:49) We're a much smaller company than Canva, but I like partnering early because then I have this this compounding advantage where um my team has already adopted this tool. It's a part of our it's a part of our environment by the time the tool is great versus everybody else just trying to like catch up and figure it out. Yeah, I feel like you get yourself a competitive advantage where you're in it, you've shaped it a year before everyone else. (30:12) But I do think we're at the point now where we're we're working with these vendors to shake these tools and and if everything goes well, they're going to be available to everybody. So then hyperpersonalization like does that become commoditized? Commoditized. Yeah. What's next after that, you know? So yeah, Stevie Casease was on was one of my first guests and uh this is probably my most quoted thing from the podcast now is like execution is the only moat. (30:38) like it's the only the only durable moat and advantage you have against your competitors and because you know there was all these Vanta clones that did it cheaper and and whatever and so our approach is just like we're just going to move faster than everybody else and that's our that's our advantage and just assume that everything is going to get commoditized everything is commoditized so how do you keep staying ahead right and you keep getting that one I mean I think it might be longer some of the some of the legacy customers like legacy companies here are really not anywhere near where it sounds (31:11) like you guys are. So I I do think sometimes that head start is longer than we think but yeah you just got to you got to keep up but it's it gets exhausting because um things are changing quickly and this stuff takes time right um and and so how you how have you approached build versus buy like what's your your mental framework for when you want to build something in house versus use a vendor? Yeah, I think it depends on Well, one thing I will say when it comes to vendors, I think I've gone on a journey. Um, totally resonates what you said (31:49) around like picking vendors at this at this time and place like you would angel checks and really backing the team and um found a vision. But I have grown a little averse to point solutions if I'm honest and spending a more time with platforms like um relevance AI is a is a new vendor that we've brought on board where you can um basically build various workflows and um AI based workflows in one place um given how much time it takes to get vendor on board like understand the capabilities build expertise in your team like for me (32:25) flexibility of being able to do many things with a platform plays another great example, right? Um yeah, is resonating more than you know the AI SDR, AI, VDR, AI account scoring, you know, um a couple examples. So that's that's one thing I'd think about on the build versus buy. I think there are some pieces that are like we should make some like foundational investments. (32:52) So the like the auto updating, you know, um of a of a CRM to me like that has so many different use cases and parts of like it's just so impactful to be able to like query or like understand at an aggregate level everything happening across tens and tens of thousands of sales calls every month. Like so much outside benefit to the company. I probably would on the side of wanting to own and control that because I know it's going to pay dividends and be a long-term new data source that we've honestly never been able to tap. So for me on something like that, that was kind (33:23) of logic around it feels like we could go for velocity and get someone on board quickly, but do I want to be able to own that and iterate on that and control that? Probably. So for me, it's around like leading to like something about impact and how how much of a foundational um AI asset it is. (33:41) I think I'd lean towards building, but we're also in a different spot where I have a ton of access to really strong engineering and product resources to support me on that just given the scale of the company. If I was at an earlier stage place, I think I would on the side of velocity and just like bringing these vendors on board and seeing what we can do. (33:59) Yeah, that makes sense. I think there's something around like you mentioned is it an AI asset and there's there's certain things that that you do want to own as a company like I think about this in terms of um you know the the knowledge models that are getting spun up you know so we've got an AI customer support bot which is trained on one model we've got we're piloting an AI SDR now that's a different model we've got guru internally which is you know queries every like guru card you can write guru cards okay but that's sort of a that's a (34:36) different knowledge base I I think the the first principle here for me is I'm trying to limit the number of surfaces yes and uh one of like your aversion to point solutions I have a very similar one it's not about a point solution because I'm okay if it's a point solution in the background what I'm really trying to avoid is new surfaces for the reps to live because it's just so delotterious to somebody's ability to focus because they're already living in their inbox, their Slack, Salesforce, Sales Loft. Yeah. Then you want them in gong with their (35:11) call recordings. It's it's too much. Yeah, we should talk about that because we've implemented a bit of a model where we have the go to market AI lead and then I've paired him with workflow experts. So it's like how do you get ext like high velocity experimentation but then also I've got like an AE workflow expert an XDR workflow expert a CS workflow expert and they are kind of the gatekeepers of what do we enable the field on right like we have to have a really clear point of view on this is how you do your job this is a day in the (35:39) life maximum four tabs you know as so we can talk through that a little bit so say more yeah that's super interesting so then you've got so this GTM AI lead that's centrally solving like AI workflow problems. And so those are individuals that are paired in in the RevOps team that are paired to those functions. (36:02) Exactly. So kind of a hybrid of a programs enablement person, but we just in addition to launching the go to market AI lead, we also reconfigured some folks's role. So we now have workflow experts that are responsible for running programs and playbooks but also having a really point of view on how to do the jobs for each role. (36:25) So we have one for AEES, we have one for XDRs and one for CS because I think my rally cry to the team is Robert our our go to market AI expert will be annoyed at me but basically my my my war cry is like velocity like let's test let's iterate let's find experiment and see what's great but at the same time I don't want to have an uncontrolled environment for our field where there is AI experimentation 12 ways you can do workflows via existing vendors and new vendors and so how do we have the balance of like both rapid experimentation but also simplicity (36:55) clarity tool and tab consolidation for the field right so the job is those workflow experts are kind of the gatekeepers of what do we actually enable the field to do when we hire a new AE you've got core jobs of prospecting deal management um where do you do those do you do those in focus tool that we have do you do that in our new prospecting tool how where do you do account research so I've got that gatekeeping relationship ship where like we are always auditing where the best workflows and ideas come from, but it (37:25) has to make sense for a rep or someone on the ground and we have to um be able to distill their jobs to be done into as little surface area as possible. Are you ready to level up your go to market strategy for 2026? Then don't miss GTM 2025, the only B2B tech conference exclusively for go to market executives. (37:45) Join a thousand other revenue leaders this September 23rd to 25th in Washington DC for an exclusive executive onlyly experience. This 3-day event is hyperfocused on connection, strategy, and execution. Expect hands-on workshops, in-depth strategy sessions, and curated opportunities to build relationships with VPs, CXOs, and founders facing the same challenges you are. (38:12) You'll stress test your GTM approach, align your team, and leave with real actionable insights from top performing leaders. Don't miss the must attend conference designed to help you boost go to market results in 2026. Visit attendgtm.com. That is a tt ngtm.com to secure your spot today. And don't forget to use the code topline for 10% off your GA ticket. So um how do you do the experiments then? So so like you're trying to do experiments and you want velocity but then where but you don't want to like cause chaos in front of the reps. So do you have like pilot groups? Do you have like (38:54) innovation labs? Yeah. Say more. You have like a it's not really formalized yet. We're still early on this. So it's not as if I have uh like a field advisory board or anything. But for every workflow we roll out, we're testing it with a handful of reps, um, two, three, four, getting their feedback and then seeing what works before we go and reenable everybody on something or we go and update our new hire on boarding to say here's what we do and how we do it. Okay. And so you're are you what are you doing to consolidate surfaces? Like this is a (39:24) thing that I'm very interested in. I think you have to be really pointed on even if three of your existing tools say they can do the same thing like AI like account research. I'll give you an example. Yeah. We believe like you should only really be doing it here. (39:44) And why? It's because we've invested in this tool and set up all the right connections into sales loft so you can do your research to prospecting in that place. It doesn't exist elsewhere or we don't believe that that other tool does it as well. Um, we've really invested to make sure that this tool where you're doing account research has all the access to our own enablement material, PMM material, so that it's tailoring that research based on our fit and your GBT. (40:08) Maybe you've got a great one, but probably doesn't have all that. So, I think it's just being really prescriptive to be honest. Um, yeah, and saying do it here, don't do it there, even though there's shiny stuff everywhere while not stifling, you know, people experimenting and finding things that we certainly haven't found as well. Yeah, that's the tricky thing. (40:26) I'm I'm airing on the side of prescriptive. It's like I don't really want the reps playing around in a bunch of different tools and figuring out their own way. Like it it's I think it's a distraction unless they are really spending the time to go deep and learn things from first principles and understand uh the prompt engineering and the workflow management like they're they're just sort of gonna bump around. (40:54) It's such a fine balance because I feel like there are the top 10% of reps who are super creative and talent that have great ideas as well. And so you can't you need to look out for those folks and make sure you're like they're surfacing all their great innovations. But for the majority of reps, I 100% agree. um started. And so how are you balancing like iter iterative improvements things that are like oh this is like obvious and simple like let's go let's go do that with you like the big bets with a ton of payoff. (41:27) Well one framework I have is like anything that touches a customer or prospect has to be done highly iterative with a very high quality bar. anything that's behind the scenes internal only a Slack alert for like deals that are stalled or meetings completed so that manager has visibility we can just launch ship and figure it out as we go right like lower fidelity is totally fine um so that's one framework I have I don't know I feel like on the maturity journey like if we were at the point of everyone doing personal experimentation (42:03) and productivity hacks um most of the use cases we're at are still at the point of just augmenting human workflows, making someone faster, more efficient, having a be better customer experience or prospect experience, like higher quality. We're not at really at the point where like we're actually transforming roles though, I think. (42:26) And so like I would love to make some big bets there. I just I personally don't feel like I'm ready or I've seen enough of those where um I'm ready to jump in yet, but we're doing a lot in that middle layer. Yeah. And so was that an intentional choice to say we're going to go we're going to go make reps more efficient? Like that's the thing. (42:46) Yeah. I think I mean that was the obvious piece that came up first which was oh my god like sales admin and so much time clicking around like a lot of the initial excitement was like okay we can make this easier and better. I think I've changed my thinking though as we've dug into these tool it's not just about time savings but it's about like better experiences like better higher quality experiences in everything that we do. (43:11) So, it's not just sending, you know, an okay email with like seven less clicks because haven't had to click around to, you know, in Zoom info to contact source and then add that to a sequence. Now, I'm actually like, oh, like you can do it in seven less clicks and actually write an email that you like have insight into your customer and their company and the person like in a way you never have before. (43:34) M so for me it's moved from yeah it started off just organically as efficiency and now I think it's really like delight effectiveness and like quality experiences that you can not only differentiate because you've got a much more efficient sales team who's like x more productive than your competitor but like one that's delivering much better and like kind of interactions and human interactions. (43:54) Yeah. Yeah. Makes makes a lot of sense. Um I want to we've been bouncing all over Yeah. Uh okay I I'm gonna ask one more tool around or one more question around this like thinking strategically about it and then we'll get into use case prioritization. So you mentioned that that you mentioned the importance of leaders being on the tools and like really being in there. (44:23) Um, first, why is that like important uh for you? And and at what level of the hierarchy are you say? Are you saying like from CRO to frontline manager, everybody's got to be hands-on? And uh so like why first off? And then what are the things that you're learning there? Yeah. Um well I think the first thing I'll say is like I think a lot of the changes that AI can deliver I mean we're transforming workflows at this stage and so unless you're like really understanding what that workflow looks like for a lot of us it's been a long time since we've actually had to go and source a contact add like go through (45:02) those seven that we talked about. So unless you're kind of like really alive to what that reality looks like today, um I don't know whether you can have your own perspective on where the efficiencies are to be gained. And so for me it's about closeness to the workflows and the reality of those that's that's really important. (45:21) Part of it's also like yeah again folks on the ground have day jobs and and they have jobs to be done and keep the lights on. Like how much time do they have to experiment? like the more seen you get like the more time we have to to kind of think expansively with all the context of the broader business um to be able to do that. And so where does it cap out? I don't know. (45:39) I don't know whether I'd expect a CRO like yourself I mean you're you're you're unique but um at a larger company should they be you know on demos and really testing and being part of these pilot groups? I'm not sure, but I think that definitely frontline managers and and above like have to be have to be really hands-on understanding the pain points in the current workflow so they can have a point of perspective on not only where to focus but what the biggest gains are to be had. Yeah. Yeah. I've been pretty clear with my team that I expect everybody to build (46:13) capability here because they need to be able to make iterative improvements to their own to their own day-to-day. It's like we're we're in a performance review cycle right now. I'm like, if anybody's hand typing their whole performance reviews, I'm going to be really mad. Yeah, for sure. (46:32) That's a that's that's a really obvious one. Um Yeah. Yeah, as opposed to, you know, you should just use Whisper Flow or Super Whisper to dictate a bunch of stuff and you just dump in all of your old one-on-one notes with that individual and and ask the model to give you themes or whatever. And and I and I think that the manager has to be conversant enough in AI that they can make themselves more efficient. (47:00) We're going to do a bunch centrally, but a bunch of the central efforts are actually to make the reps more efficient. But I think but I'm I'm looking to the managers to try to find opportunities to make themselves more efficient and then we'll codify those and and roll them out. Yeah. The my leaders gave it some name recipe books. They're like building these recipe books of stuff um that that they're learning. (47:22) So I I agree. I think I think people just have to be hands on. Yeah. I don't know where this like you know I think we at larger organizations you have a lot of middle managers who are like prof I don't know you've got you've got a great framing on this but professional people managers and I think even the example you gave like the ability for us to be effective people leaders in a world where we have so much access to data and you can know what's going on in the ground like do you need people who are just translation layers of you know from the work on the (47:52) ground up all the layers I think that's going to fundamentally change even with just like how we show up at work do dayto-day. And so I might be controversial. I think that's going away. And so if you're not a leader who yeah, if you're a leader who kind of sits in those middle layers and is just about organizing the work, like AI can organize the work for you already. (48:18) What where do you want is your job to take information from the team down here, repackage it and give it to a team up here? Yeah. Repackage, synthesize, relay up like no. you know, even the most basic user of chat can do that already. So, yeah, that's a hot take, but I think I'm curious to see how quickly it'll evolve. Yeah, totally agree. Yeah. And we're trying to do a bunch of this like we we just built a a we just built new workflows for our MBR so that it takes the information that people are are using for their written weekly updates and repackages that, repackages it as a monthly update. Yeah, you're gonna have to go in and and the the ma the leader will have to go in and (48:57) groom. But if the model can give you a pretty good starting place, that then that's that's awesome. Like even for the podcast, like I I I have a very very lengthy prompt and I'll take the transcript and put it into my clawed project and it just runs the same project instructions and it gives me like a version of my newsletter that's 80% there, you know, like it would it would normally have taken me 3 4 hours to write, you know, a lengthy article about every single podcast and now it's 25 minutes for me to just like I'll I'll get the output. I'll I'll edit as an artifact and be like no like (49:38) my notes this was a more interesting point and so I'll just copy paste from my notes like no swap out the third point for this and here are my notes and like take it from the transcript fix this oh you messed up Jessica's intro and then I'll do like a hand edit in Substack and so that's a 25minute workflow now that used to be when I first started the podcast I tried to do it by hand and it was like three hours. Yeah. (50:11) And and I wanted to write I wanted to write a couple by hand so that I could feed it to the model and be like this is what I want the newsletter Yeah. to look like, you know, just like a multi multi-shot prompt. Um and I think managers have to be able to do stuff like that. And I think we should be excited about that too because it's like it feels so high leverage. It's like Oh yeah. nice performance team with like infinite resources like it's kind of a very addicting feeling. (50:37) So I hope people are excited about it. Yeah. But going back to your point I think where folks get stuck is uh LinkedIn makes everything seem like magic and everybody says that like in their demo or their marketing copy it's like oh just put in your thing and then it's like miraculously awesome. And that's not really the case. (50:58) Like it takes a bunch of you try it, look at the output, it's sort of wrong, you go fix your prompt, you try it again, you run the table a third time. If it's like clay, you just have to go back and forth and back and forth and you know the thing that the thing that takes you an hour, it's now you're three hours into trying to build that workflow, which feels frustrating, but then you know now the thing that took you an hour before might only take you 10 minutes. (51:23) You have to have the patience. You have to have the patience to and the interest to to tinker. Like I love tinkering. So it's it's fun. And I Yeah, I have some envy though for like uh companies smaller and more nimble than Canva. Just just the scale that we're at. (51:43) I spend time with the earlier stage companies and we'll be talking about ideas and then you know the things that we're actively working on and hope to launch in months and then you meet again in a week with them and they're like yeah we just we just built it. Um which is so yeah we've got yeah we've got processes and and and stuff. we've got to um we've got to adhere to as well. (52:01) But yeah, it some of these stuff like you know we're working with um even with Clay like bread and butter is on enrichment but there are some enrichment things that we want to achieve that we have the luxury of they they are such great partners to us. We have an amazing CSM folks on the product team but we're working through things over months to tune them and get them to exactly what we're trying to achieve. (52:19) So this with vendors and partners but it's not it you know the very simple use cases again super easy to prototype like really hard to get it to to do what you you need for the business. Yeah. Um so I want to talk a little bit about use case prioritization. We've talked a little bit about you you started to attack um the areas of efficiency trying to make people more productive. (52:46) How did you think how rigorous was the process of you identifying okay like these are the places where we're going to go? Is it like a big meeting you take all the ideas? Did you spreadsheet them? Like how did you decide on what gets what gets prioritized on the road map more organic for us? I think we all have really as like business leadership have like really good intuition about again the framing is like the bottlenecks in the business, right? So um I think we had a really good sense of those were the places. (53:12) The other thing we added on were like um what are the more transformative bets that we want to make where you know solutions may not be proved out but tapping more into the curiosity of in addition to what's challenging us today like what could the future look like? Um so that was the second way. The really interesting piece though, and again this comes back to why I feel so strongly about being a leader who's in the detail, leads from the front, being close to the workflow is like I spent a lot of time and my team spent a lot of (53:41) time like interviewing reps, looking through Salesforce, looking through detailed activity feeds in Salesforce to get a real sense of like what's going on on the ground in a way that like the gongs of the world don't even aren't even able to show you, right? Like um discovering like what are what's the content of the emails we're sending out? what's the what are the case studies that we attached to our um our prospecting sequences? What's actually happening on the ground? And I would say we had a lot of aha moments from that like very laborious detailed (54:11) process of just sitting down, shadowing, looking through activity feeds that were also another source of ideas. So for us, I would say it was more of an organic process, but they were the three things that I think have really helped us hone in on what like where are the five or six use cases that we're currently investing in. (54:35) Yeah, I could not agree more strongly about the ride along and like being in the details. My my sales leaders are all like doing the job actively with the reps. like my director of BDR will sit down multiple days a week and make calls like executing the the exact job that the reps are doing because you learn so much or sitting next to a rep and watching them work. (54:57) It's like wait why why'd you go over here? Oh, like I wanted to figure out this and that and like wow like you just you you'd be so surprised by why by how far people veer from from the playbook. And a friend of mine, Tess Whitaker, who's the VP of RevOps at uh and strategy at at Zoom Info, she did a day where she was a BDR and like made dials with her team. (55:23) Actually, my my HRBP and my recruiter are both doing that with uh just to like learn more about the day-to-day of the of the job so that they could be more effective at what they're doing. And I loved it and and they'll actually be both great at it, which will be fun. Yeah, I know. Well, I'm going to tell my HRVP and uh and recruiter to to do the same. Yeah, that's a great idea. (55:42) Yeah, it's it's but the the macro point is you have to be close to the details to to make good decisions or else, you know, the the funny thing is when you see or when you're in organizations where a decision maker is like, "Oh, we're going to change this workflow or we're going to change the the comp plan in these ways or we're going to change our positioning. (56:10) " and you're like, well, you couldn't have been you you cannot have spent any time with a rep or a customer in a long time to make that decision. It's it's it's uh it is such an important thing and and especially for ops leaders like that's where I have my greatest self-consciousness which is like if I'm if I'm not doing that like I can't show up in a credible way saying I have a job and I'm here to make you successful. (56:28) So yeah. Yeah. Um so let's switch gears and talk talk um change management a bit. So uh this is a big change for people and I think especially frontline reps there's a lot of worry that their jobs are going to be taken by AI. Um there there's you know people of all seniority levels that are that have sort of these concerns. (56:56) How are you approaching change management so that the teams feel excited about AI, not overwhelmed, not scared that it's it's taking their jobs? What's what's been the approach there? I think again I think I'm in a luxurious position in that my day-to-day just as a company culture we don't have a ton of that resistance. So um that feels lucky because I I I don't think that is the norm. (57:22) Um, look, I think giving people those moments of delight like that you talked about in terms of even the newsletter prep of like how high leverage it feels to almost be like I think about our four ops analysts who are otherwise enriching and and working sales like support tickets like the moment where we've trained them on clay and they can see the power of it like the actual emotional feeling for them is like oh my god like this saves me x like it would have taken me to do this and I think you really quickly get that buy in when you find the ways to have folks on the tools and they feel this (57:59) moment not of threat like it's easier to feel like it's a threat when you don't know how it works or how it can supercharge you when you're and turn that feeling of threat into feeling of leverage then I think for the most of the folks right folks it's like excitement around wow I can um I can operate at the top of my pay grade I can do the things that I already knew felt like very or like automatic wrote tasks. (58:24) And so I think that's been the biggest piece that I've seen that gets not only just buyin but like excitement and people raising their hands to see to say can I be involved in this? How do I carve out more of my day to spend time on this? It's like moments of de delight and that feeling of like incredible leverage that I think um you and I at least know well. Um, so that's one thing and I think the second thing is like bringing people in the journey. (58:48) Like our BDR leader is is the subject matter expert with all of the outbound prospecting work we're doing. Um, and so this is a career moment for them all as well around how they can reshape and transform the roles that we're doing. And that stuff is never going away. (59:08) The human element of selling and supporting customers is never going away. And so it's like how do we all get hundred times not only more efficient but like effective at bringing that value to customers. So I'd say yeah. Yeah. We're both in advantageous positions when you know a company is growing and you can attract great talent. I I don't find we have any of this resistance because we we've largely deployed stuff that just makes the team's lives better. (59:32) like if you're not writing in your own CRM and you have better quality leads and contacts to call and you know then it's easy to to get buy in. I think there's we we we're talking a lot about automation in the in the customer onboarding journey and I've I've had to have the conversation with them. (59:55) It's like, look, I want to automate all of the lowest value parts of your job and cuz I've got a laundry list of things that I would rather have you doing. And I and it was when I explained that part of it, it's like look, like you guys can't spend any time teaching a customer how to use the tool or planning their marketing launch like we're going to because we make websites and apps for for restaurant owners. (1:00:12) It's like you you know, we don't spend any time planning how they're going to announce this to their guests, but I want you doing that. And so I think that was the thing that was helpful for for that team that was a little more skittish about it. Yeah. (1:00:32) Um it's, you know, like I want to to I want people's level of abstraction to to be higher and I hopefully I think we're seeing this you're definitely seeing this in software engineering. Yes. Yes, you know they're the the lowest levels of software engineering are definitely like getting abstracted away like they're they are uh diminishing in importance and in volume but then you know your your senior engineer now sort of acts like a principal engineer or an architect and yeah and how do you teach skills to bridge that gap is an open question that I don't have an answer to but um I think there's there is a path where everybody (1:01:07) could be doing something that's like more impactful than what they're doing today. Exactly. Like BDR is doing lead research. Come on. It's not fun. Yeah. What are you doing? You're reading and then you're writing. Like what about thinking how do we get BDR? Like this is this would be my pitch is like how do we get you to be better experts in companies their industries like like understanding trends making personal connections and not doing the stuff that you know they they they know and feel they don't enjoy that doesn't feel high value ad for themselves and (1:01:38) doesn't feel high value ad for prospects as well. Yeah. Um so last question on this this topic of prioritization. How are you personally prioritizing your time? Because you can get pulled in so many directions right now. Like there's so many Twitter threads and articles and stuff that I want to read and demos I want to take and so how are you how are you juggling it all today? Oh, I love that question. I'd be curious how you're doing it as well. (1:02:08) But I um I want to spend more time in this space. I want to spend more time understanding what others are doing, which is why I'm so excited for this conversation. I want to spend more time with vendors and that like some of the stuff we were talking about earlier I want to spend more time on the tools shadowing building and iterating and so for me it's like even as an ops leader I I'm trying to rethink how I have spent my time over the last 5 to 10 years too like what are the keep the likes on stuff that don't feel high leverage in this moment right now how do (1:02:36) I get more leverage through my team and carve that down so you know we go through the motions we have our regular weekly monthly quarterly cadence how do we how do we get in a better spot that I start to diminish that stuff. (1:02:49) So you free up I don't know you know what used to take you 5 days and that's where a lot of the productivity stuff comes in as well takes you only three days so you can carve out the time where you know half your time is spending leaning into this cuz I do think it's a competitive advantage but it's hard because you know transformation hasn't happened such that we don't need to I mean there's been a lot of gains made the last 5 years but we still need to run a forecast and we still need to all those accountability and visibility conversations. (1:03:14) Um, so it's hard, but I'm actively working on it. And my goal is like how do I free up two days a week of my own time to spend on this, but that's two days a week that I wasn't spending on this previously. So, um, yeah. How are you doing? I'm trying to get leverage with AI. (1:03:35) Honestly, it's it seems like a a forced answer in this context, but I think yeah, the only way to to get that space is to try to get the low value stuff off your off your agenda. Yeah. And so, um, we've got a really good team. That's that's the other thing that helps a lot. Yeah. I have people on my team that uh are massively capable and I'm continuing to push them to take more and more and more and we want to build more workflows that are automated and whether it's with AI or not but just just give repeatability um because that's such a that that delivers so much scale honestly like I (1:04:14) just like replaced my doom scrolling time with Twitter AI time Like I think I think if I I was never a huge social media person, but I think if you look at my Twitter utilization, it probably went from like an hour a week three years ago or four years ago to like an hour a day every day. (1:04:43) Like when I'm just sitting on the couch with my wife, like if we're watching a show, I'm like always like on AI Twitter. Yeah. Yeah. Well, well, now it's AI Twitter and I'm like lost in like I'll be like lost in these threads and I'll see cool things and my wife's like, "You're not even watching the show, are you?" I'm like got an earphone in. I'm watching somebody do cool MCP stuff that I haven't seen before. (1:05:01) And I think you just got to like fit it in a little bit. There's some good podcasts out there on it. I'm having a lot of conversations. I think going like I love that. And I think um I'm having I'm finding a lot of great ideas and learnings through to through finding out like the like-minded peers who are you know leading and innovating and sometimes you stumble across each other because you're working with the same vendor or sometimes you know it's through the LinkedIn feed or whatever but such high quality conversation similar to this around it's not just the amazing demo screen grab (1:05:33) that you see on LinkedIn but like okay when you actually get into it how did you do it what are you seeing? Um, yeah, that's informed a lot of like how we've approached it as well. Yeah. And you're speaking at Clay Sculpt in September. That's right. Yeah. Yeah. In good plug. People should come see you talk and I'm going to try to come to some of that because it'll be a whole room full of interesting interesting folks to talk to. Exactly. Um, okay. (1:06:00) Let's move to rapid fire because we're about to to run out of run out of time here. Uh, more general questions. So, what um what do you think separates a great GTM ops strategy leader from just like a good one? Oh, I love this question. I have this framework of functional versus business leadership. Um functional leadership, you've done the job x halfozen times in six different contexts. (1:06:30) You've uh you're deep on the craft itself. Those leaders are amazing. Absolutely need them. What you also need though is business leaders not necessarily as you know the pattern recognition doesn't need to be quite as strong in the craft itself on the things like you know in my world enrichment roe you know but understand the broader business context and can solve problems from first principles I'm a business leader I would say kind of my training and my approach to how I show up um in the work world and I augment myself with functional experts. But I think that's like and you can be different people at different time for (1:07:09) different styles of leaders. But to me, I think that business leaders, right, who are able to build functional leaders around them, can really take a different approach to the ops and strategy world, which can otherwise be very much just like running the ship and kind of batting away the the conflicts and disputes that happen on the sales floor. (1:07:34) Yeah, I think that's very I think you could say that about a lot of jobs, you know, that like if you're a first principles problem solver, uh you have a lot of room to run. Yeah. What's the hardest lesson you've had to learn in your career? I think I mean this is a blessing and curse out of being in really fast growing organizations but when things are going well the job changes every six months and I think honest with yourself every six months around one do you have what it takes to you know be in this next stage of company hopefully the answer is yes but sometimes the answer might be maybe or no and two are you ready to sign up for (1:08:10) like basically another another sprint and another run in it in what may on the outside look like the same company but it's actually at a really different scale and I think yeah being at Asana at that 60 to 600 million journey and now on this rocket ship that is Canva like that's something that I'm really I think about and I think it took me a while to learn that um but I think it's something I encourage all my teams to think about as well. (1:08:32) It's both like do you have what do you have what it takes and and do you want to do it? Yeah, the do you want to do it is a is a big piece of it because there's no resting in a high growth environment. Yeah. They're like, "Oh, great. You did your job and the company's winning. Now the next thing that you're tasked to do, you've never done before. It's you're like sort of out of your depth. (1:08:50) " Yeah. And so you have to keep operating with that like pace and intensity. Yeah. I think you owe it to yourself and the company as well. Um hopefully pays off by things keep keep going well. Yeah. Okay. Last question. What's the best thing you've read in the last 12 months? Oh, honestly, tying back to tying back to a lot of what we've talked about, it's kind of a LinkedIn Twitter feed. (1:09:16) Like I that's where I'm getting all the latest ideas if I'm honest. Um there are no books being written on this stuff yet. Um and so it's it's the LinkedIn Twitter feed from both vendors and other folks like you and I who are discovering and and wanting to share what they're working on. (1:09:35) Um, that's been to your point on this the scrolling time kind of where I spend time. Yeah. Who are the best uh AI follows? Who are the ones you you go back to the most? I get asked this all the time, so I'm putting together a list. Well, it's weird because it's actually sometimes vendors. Like I I don't I don't often say that, but like if you look at the stuff that Clay puts out, the momentum, attentions of the world, cursor, that's right. like it's it's kind of cool what people are showcasing. (1:10:05) Um I'm always a little skeptical because you know they are they are folks with products as well but like it's um they're able to showcase I think innovation in a way that maybe other people are not as comfortable showing right now. Like would I show all the stuff that we're doing our clay tables? Maybe not. Um they're able to do it in a more anonymized way. (1:10:22) So, um, yeah, I think with the pace of iteration, I I rely a lot on on some of those, um, accounts and the amazing, you know, 15-second screen recordings that they're sharing out. Get maybe it's not exactly what we would build, but actually get the creative juices going and start to help you like calibrate on what's like what are the boundaries of what's possible, what's possible. Yeah, exactly. (1:10:45) It's funny because we were both nominated for that winning by design AI award. I was like, Clay should just win all of these. Like, I don't know. Like I don't know why anybody else is is is nominated. Like they're doing way cooler stuff than I'm doing. They're they're uh they're on another level. Yeah. (1:11:03) And then you partner with them like we've got, you know, then you partner with them and then you you together find like even more exciting things to build. And I think that's just the phase that we're in as well. They're bringing ideas and then they're also co-shaping with like the canvas and the owners of the world like what's next? Yeah. Yeah. Well, this was awesome. I knew I was excited for this one, Jessica. (1:11:20) and it definitely like lived up to the lived up to my internal hype. So, I appreciate you coming on and uh sharing so much. This is I think people are really going to like it. Yeah. Hope they get to catch up in person as well. Yeah. And people should come see you at Sculpt in September, whatever it is in San Francisco. (1:11:37) We'll we'll plug Clay the Clay conference forum. Yeah. We'll see everyone there. Thanks for having me. It's been fantastic. Thank you for listening to the Revenue Leadership Podcast. If you enjoyed it, don't forget to subscribe and you can find a link in the show notes. (1:12:00) And be sure to leave a fivestar review, share it with your network, and please join me next Wednesday for another great conversation.