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Guy Yalif is a seasoned B2B SaaS executive with over 20 years of go-to-market experience. As the co-founder and CEO of Intellimize (acquired by Webflow), Guy brings a unique perspective from his journey through iconic companies like Microsoft, Yahoo, and Twitter, as well as his background in aerospace engineering. Guy holds a bachelor’s degree in Mechanical and Aerospace Engineering from Princeton University and an MBA from Stanford University.
Discussed in this Episode:
- Learnings from each major company in Guy’s 20+ leadership career: Microsoft, Tradeweave (first employee and executive committee), Yahoo, Twitter, BrightRoll and Intellimize.
- Building ‘opinionated products’ and the importance of customer intimacy
- Lessons learned from scaling Twitter’s ad business from zero to $650 million in three years.
- The challenges and rewards of founding and growing a startup for nine years.
- Strategies for building relationships with PR outlets, reporters, and analysts.
Highlights:
(5:22) The power of customer intimacy in product development.
(15:41) Scaling Twitter’s ad business and managing hyper-growth.
(26:54) The existential dread of being a startup founder.
(37:56) Building relationships with PR outlets and reporters.
(45:40) Debunking the myth of sacrificing personal life for startup success.
(49:07) The effectiveness of small group events in go-to-market strategies.
(31:55) One thing revenue leaders believe to be true that Guy thinks is bull$***
(49:07) One thing that is working for Guy in go-to-market right now.
Guest Speaker Links (Guy Yalif):
LinkedIn: https://www.linkedin.com/in/gyalif
Host Speaker Links (Scott Barker):
LinkedIn: https://www.linkedin.com/in/ssbarker/
Newsletter: thegtmnewsletter.substack.com/
Where to find GTMnow (GTMfund’s media brand):
Website: https://gtmnow.com/
LinkedIn: https://www.linkedin.com/company/gtmnow/
Twitter/X: https://x.com/SalesHacker
YouTube: https://www.youtube.com/@GTM_now
The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/
Resource we Recommend:
- HG Insights. Feeling that AI FOMO? You’re not alone. That’s why HG Insights created The Next Generation of Sales AI report — to calm the FOMO and help you bring AI to your GTM teams. It includes a breakdown of the Sales AI landscape, adoption of GenAI and Sales software across buyer groups. Plus, an analysis of the top 75 trending sales AI tools. Why HG Insights? Simple. They’ve been writing market reports for years as the pioneer of tech adoption and market insights. Trusted by GTM leaders at the likes of Snowflake Five9 and Google Cloud to improve GTM efficiency. Thinking about AI for your sales team but unsure where to start?
The GTM Podcast
The GTM Podcast is a weekly podcast hosted by Scott Barker, GTMfund Partner, featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Episode Transcript
Scott Barker:
[0:00] Hello and welcome back to the GTM podcast. I have no idea what episode we are currently on, but it’s getting up there. And thank you all for rocking with us every week. Super cool to see the continued journey and more and more people tuning in every month. And we’ll keep the good guests rolling. And I got an excellent one this week and super excited to be hanging out with them. I am joined by Guy Yalif. Guy, welcome, man.
Guy Yalif:
[0:29] Thanks, Scott. Thanks for having me. Great to see you again.
Scott Barker:
[0:31] Good to see you, man. Good to see you. We were hanging out in SF somewhat recently and finally convinced you to come on the pod. So excited to have you.
Guy Yalif:
[0:42] Excited to be here with you. You’ve got some great guests. I hope not to bring down the average to better.
Scott Barker:
[0:48] Let’s get right into it, man. So I guess I should do a quick bio. I’d like to give a little bit of context for the listeners.
Scott Barker:
[0:55] So Guy Yalif is a very seasoned B2B SaaS executive, over 20 years of go-to-market experience. For the past 15 years, he has really excelled as a marketing leader, following a decade as a product leader. So really interesting kind of shift there. And then originally trained as an aerospace engineer. So I can’t say we’ve had an aerospace engineer on the pod. So you are number one. um so just really interesting what like combining this text technical expertise with strategic business leadership and uh that has converted to four successful b2b sass exits uh you’ve worked at iconic companies like microsoft yahoo twitter and extensive experience which is super relevant right now in real ai and you’ve been engaging deeply in that field long before it became mainstream and we all had chat gbt and it’s every single article that we’re all consuming now um but uh you’re most recently also the co-founder and ceo of intellimize which was acquired by webflow so congratulations and uh holds a degree of mechanical and aerospace aerospace engineering which again first time we’ve had it and uh mba from from stanford but uh i gotta dive right into to AI because it’s in your bio, it’s right there.
Scott Barker:
[2:19] And you’ve been in this space, as I said, a long time. Are there some assumptions about AI that you think the majority of folks in go-to-market might be getting wrong?
Guy Yalif:
[2:33] Uh i think a bunch and you know you keep mentioning ai isn’t the line from excuse me aerospace from aerospace to marketing like that’s a straight line that’s a well-trodden path very.
Scott Barker:
[2:43] Very linear for.
Guy Yalif:
Sure um i think that even those of us that have seen multiple generations of tech changing the world are uh really watching the speed of this and i think it is faster than anything we’ve seen before but i hope none of us lose sight that it’s a means to an end you know the the customer they are true north we should not lose sight over whom are we going to delight well enough that they’re going to give us money that’s what matters and focusing on that for our product and less on the competition and less on ai in my humble opinion is the place for us to go and for our messaging You know, we would never say GTM now is an electricity company because you use electricity or an internet company because you use the internet. I think in not too long, we won’t say these are AI companies.
Guy Yalif:
And so I think that’s one, really focus on what new use cases, what degrees of freedom does it enable you to do? One two is that all ai is what we’re seeing right now what we’re seeing right now is as we’ve heard generative ai there have been other kinds of ai and telemise happened to build one of these other kinds predictive ai that have been around forever for as long as we’ve had you know uh almost as long as we’ve had computers and what’s interesting is each is suited to different tasks you know generative ai is it’s based on stats it’s applied statistic well that’s not too helpful when you’re using your accounting system and you don’t want probabilities right you need something to be deterministic every time uh and um and and so to choose the right tool for the job i think can be can be really helpful yeah.
Scott Barker:
[4:31] Yeah couldn’t couldn’t agree more i mean i feel like anytime we have these big technological bumps and it’s funny you say internet companies because like when the internet first came out people were like yeah we’re an internet company right and.
Guy Yalif:
[4:45] Then totally.
Scott Barker:
[4:46] Blockchain was gonna you know revolutionize the whole world then there’s all these like blockchain companies and it’s like don’t lose sight of no you’re a company that’s solving x and your customer doesn’t really give a shit what technology you’re using if it’s the internet whether it’s the blockchain whether it’s predictive or generative ai it’s like what is the problem you’re solving and you know yeah i think that’s a great uh.
Scott Barker:
[5:12] Kind of comparison you said of like we all use electricity every day so are we all electricity companies uh at the at the core um but no i like it it was it was funny too not funny just interesting to see all of these recent vc ai funds you know the 500 million dollar ai fund and all of this money getting raised on the premise of that and you know we kind of looked at it and And we’re like, that’s just a software fund. Like every new software fund that’s getting created has some former elements or will be using different versions of AI. So it’s just the next natural evolution, which is interesting. So something that stands out for me in kind of your background is you have 20 years of operator experience, 20, 25 years of operating experience. Experience before starting Intellimize. And I think that there’s this sort of idea in Silicon Valley, and it’s perpetuated by the media, that startup founders are all super young, maybe straight out of college, hungry, engineers, hustlers, and that’s the archetype for success. But at least from us in the four years of starting this fund, and knowing that we are focused on B2B I think consumer might be a little bit different.
Scott Barker:
[6:39] We almost exclusively invest. And when you look at the data and the ones that have gone well and not as well, all these founders have lived or earned operating experience in a given sector, in a given category. They intimately know a problem well. And there’s just so many lessons to learn. There’s tribal knowledge in every sector. And it’s really hard to solve problems for other businesses before living them yourself, which is and you know there’s there’s outliers but i guess would you say that each stage of your operating journey better prepared you for ultimately the the founder journey and a successful one.
Guy Yalif:
[7:20] To the extent that each step builds on the previous very much so and with humility to your point about the previous operating experience it’s just a big set of mistakes right like hopefully we make a new set in you know leading a company and starting a company um and hopefully those battle scars help inform like where are you going to gold plate what you’re doing and future proof it where you’re going to duct tape and just get it done for today and somewhere in between i feel like in everything we do from writing the code to marketing to sales process and more that’s a choice uh and you know hopefully also along the way you’ve built a set of relationships that are you know if all is going well helping you do a better job beating your customers where they are because you can get the straight scoop from folks and and have them tell you no that really does suck like that doesn’t solve the problem and that’s gold that feedback early on um and to your point, hopefully then you can do a felt experience job of problem identification rather than a logic in your way there. Both are valid, but you probably have a bit more muscle memory for the felt experience version of that journey.
Scott Barker:
[8:42] Totally. I look at it, I think you put it a great way. It’s just like those 20 years were just a series of mistakes. And you learn that on, and, of course, wins along the way. But you get to learn that essentially on someone else’s dime. I’ll just give a random example. If someone spent the last three years trying to solve a problem at Klaviyo in, let’s say, the e-commerce space, and they had a big team of people and a big P&L for their business unit that they ran, and they spent all this time and money trying to solve a problem, and they kind of get close to it. And then things shift to Klaviyo and they’re like, oh, I’m going to spin this out. You’ve just got like a bunch of basically free R&D before you ever invest. And it’s basically just all the mistakes that they made before starting the journey.
Guy Yalif:
[9:37] So, so true. And hopefully, you know, you’re adding value along the way. And, you know, I can tell you that the previous managers would point out a bunch of those mistakes. But in particular for Intellimize, my co-founders, Jin and Brian, whom I’ve had the privilege of knowing for 20 years. They led a several hundred person team that ran the predictive machine learning that personalized the Yahoo homepage. Back when that page mattered. Back when it was the most popular page on the internet. Not that it doesn’t matter now, but it’s different as we know. And that was… Learning that was incredibly expensive at scale you know 100 million impressions a day billion user profiles then they went and created yahoo’s content recommendation system while what we built at intellimize does not equal either one of those things, one of the things that made us comfortable about the lead that we had in market was that a bunch of freshly minted cs phds would not take the same path we did they would go do other very logical things, but they didn’t have the practical battle scars about which the textbooks haven’t yet been written to know, oh, wait, this path is much higher probability than that one. And we were like, great, they’ll take that one for several years before they consider this one, to your point about some of the benefits of the previous mistakes.
Scott Barker:
[10:56] Yeah, I love that. And I want to jump into your time at Yahoo a little bit more, but let’s actually start at the beginning. So you started at BCG, I believe, and then you were an intern at Microsoft, and then you went to TradeWeave in the retail kind of SaaS space. What did you learn in those really early, those can be really formative years that you pulled into success later in life?
Guy Yalif:
[11:22] At BCG, it was the classic, you know, how to think, break down problems. The consulting mindset was quite helpful there. At microsoft there was uh i won’t get specific but the ability to pay to play for some things that shouldn’t be pay to play was was uh eye-opening uh in terms of you know feedback folks would give no shade on microsoft it was industry practice nothing specific to microsoft um and then braid weave it’s funny you call it sass because back then we were like we’re doing this really cool thing it’s called a multi-tenanted hosted app which today we would call sass but back then the term wasn’t a thing uh and i um a big learning there we were doing.
Guy Yalif:
[12:06] Basically buying collaboration software in general merchandise and apparel department stores think polo is selling to macy’s and we would help bring transparency and planning pre-season mid-season and after the end of the season for these seasonal businesses product worked the ceos of polo and macy’s and dillard’s and uh ralph and all these like they were in and the founder of the company had relationships with all of them that was great they were super fired up the users the buyer and the vendor they did not want to use it why because it was transparent and they were used to lying to each other and they made a lot of money off of that lying and so they like there was a lot of margin to be had in the lying that they did and that was industry practice and uh this product got in the way of that and so better understanding the user versus the buyer which i guess in b2b sass you’re like well yes of course that’s a buying committee but in this case they were really different people right one was the ceo of this multi-billion dollar company the other one was a day-to-day buyer uh was humbling uh way to learn.
Scott Barker:
[13:12] Yeah I mean it we see that still all the time in SaaS right you look at an example like sales tech where you know have all these analytics and reporting for maybe sales leadership but then And when if you’re actually using it, it’s just adding more work to your workload. So there is always that disconnect. How do you coach people? And how do you now think about sort of closing that gap between the user and the buyer? Because you’ve got to make the buyer happy. They’re signing the check. They’re signing the renewals, the cross-sell, up-sell. Do you have any sort of strategies for shortening that gap between the two? and the expectations?
Guy Yalif:
[13:58] My humble opinion, it’s literally what you just said, which is ensuring that there is something in the user’s self-interest that will make it better for them and makes their life easier, not harder. And it is as simple as that. So would we have started TradeWeave had we gone and talked to all of the other users, talked to the users and understood that? Maybe. Would we have changed how it was built? Almost certainly. To enable them to keep doing the things they wanted to do. Maybe we would have built in margin calculators so they can have their internal number and a separate external number, something like that to help address that need. To your point about sales management, it’s, you know, how many people listening will raise their hand and say they have, you know, a problem with AEs and their partners entering data into Salesforce? Everyone, because it’s this, you know, it can feel like a big tax. It was one of the motivations for us to create Intellimize where you had existing tools that did A-B testing that basically gave you info, it basically caused more work you then had to go do something with it and telemise would go take the action directly uh uh on your behalf when you wanted it to and net save you time and that like those are some of the things that that they come to mind at conceptualization rather than once you’re you know out and and and running running into the issue yeah.
Scott Barker:
[15:22] Yeah um absolutely so then Then, I guess, the next step from there, so then in 2005, you make the jump to Yahoo. Is Yahoo where, it sounds like that’s where the gears started cranking for what would become Intellimize? I think you also met your co-founder there. Is that right?
Guy Yalif:
[15:41] I did. I was very fortunate that TradeWeave was acquired and then went to Yahoo and met my co-founder running what at the time was the world’s largest web hosting company, which is full circle now working for a website uh building uh managing and optimizing company um and uh we had a few hundred thousand paying customers were fortunate to grow them to a couple of million through probably the biggest lesson in my career um uh which was about the customer being true north and finding the problem you’re going to solve for them when i joined uh the job from the gm of the BU was, he said, hey, I was product manager at the time. Jin, my co-founder, was an engineering leader. And we were leading this team. And they said, hey, we have our roots in telecom. The game we’re playing is to make more features findable. So I forget the number. We have 100 features. Go make 200 features findable in a dashboard. Great. We turned the crank. We did that project. Then we went and spent some time.
Guy Yalif:
[16:44] Getting to know our customers in more depth we called them follow me homes of course with permission but then go watch them in the office doing their day-to-day job beyond our product first there were moments of like oh crud like they have a yellow sticky attached to their monitor for this thing that’s in the product right in front of them okay and then we’re like wait a minute actually we learned 40 of our customers are sole proprietors 95 or five employees are fewer, they don’t aspire to learn what we aspire to teach them they don’t want to learn the 200 or 100 features in fact their ideal product is to stick money in one end and get leads out the other this is 0405 when building a website wasn’t a given for a company they just wanted to run their business and so we literally did a 180 on the product we did not we took away choice we built a highway through the product that was simple opinionated guided them because we had done this they had not uh and it was um fortunately wildly successful we grew from 50 million to 115 million in revenue in like two and a half three years all of which was based on the opposite of what we thought of the game we thought we were playing uh and that customer intimacy was was the driver of that i.
Scott Barker:
[18:01] Mean what a what a powerful lesson and one many today can also probably feel we get a lot of founders listening to this and you know many it can it can feel like you’re one feature away from hyper growth you know like all.
Guy Yalif:
[18:21] The time you’re like.
Scott Barker:
[18:22] Oh if we just we just build this thing and look at our customer base and then only you know 20 of them if they adopt it then look at all this money that we’re gonna you know bring in and um i think that exercise of like really slowing down, on this follow me home thing is hilarious. Would you actually go physically to their office and watch them for a day?
Guy Yalif:
[18:44] For a few hours we did, yes. And it was really eye-opening. At TradeWeave before Yahoo, we had done some of that. I was very lucky to be married to our user. My wife was a buyer in retail. We were doing this for retail. And so literally in the middle of meetings, we’d be like, how does somebody do this? Yeah, we’d call the bat line. We’d be like, Monica’s my wife. Like, Monica, how do you do this thing? And we literally went to her office, saw maybe they were green screen terminals. Either way, they were very not what we have now and watched her doing her thing. And we did the same thing at Yahoo. Yeah.
Scott Barker:
[19:16] I love that. I’m trying to… There’s no reason… People wouldn’t sign up for that today still you know like if you’re a happy customer at a software company and the leadership comes to you and says hey we want to make our product better for you we want to intimately know your job we’ve done interviews we’ve had many discussions with you do you mind if we actually come in and watch you do your job uh i bet a surprising amount of people would actually take you up on that. And I don’t think I’ve ever heard someone actually doing that.
Guy Yalif:
[19:54] I think to tell them your point, we’d like you to influence our roadmap. We’d like you to influence how we frame our product. We’d like you to influence how we serve you is sort of the explicit value exchange.
Scott Barker:
[20:07] Yeah, yeah. You also said something there that stood out to me was this idea of building products that are opinionated, that have a point of view on, hey, we work with a lot of people that solve the problems that you’re trying to solve every day. And we have, through extensive research and data, decided this is actually the best way to do something and the fastest path to the result. And I think for a long time, it was almost about giving complete control and customization in software and like, hey, you can do things how you want to do it. And people were almost scared to have a point of view. And it feels like that is changing and people want to be told, especially now with AI, people are feeling like a little bit lost. And how do I engage with this? From your years as a product leader, how did you think about creating a point of view when you’re building software and making it have an opinion?
Guy Yalif:
[21:13] It really was thinking hard. As a marketer, I think the same thing. What’s the job we’re doing well how that’s it it’s really that simple and then how do you optimize for that in your messaging in your pitch in the product itself uh while leaving paths out we used to call them trap doors i don’t know why but you know to complexity and control if you want it uh and to your point it’s exactly what you said scott we just have more reps at this right we’ve seen millions of these you’ve seen a couple if you would like our advice we’re happy to build it directly into the product if you don’t no problem you can have total control but if you want and most do, The other thing you made me think about meta level one level higher is it does feel like there are generations of software in individual categories that go from where the super easy to use one and then you add and you add and you add and you upsell and it gets more expensive and you have more control and then somebody comes to supplants with something really simple and you go through that cycle over and over.
Scott Barker:
[22:15] Bundling, unbundling, bundling, unbundling. Yeah, totally. And yeah, I like this idea of sort of have a point of view, have an opinion, guide them to the outcome they want with the least resistance, but then have these, you know, you can choose your own adventure if you need to. And the complexity is there if needed, but we’re not going to throw this complexity at you right off the jump.
Guy Yalif:
[22:42] 100% in product and in marketing you made me think now um i think this manifests as not creating your messaging or your website or your collateral by committee it’s so i feel like clear so many times when you when you set up their home page is you know 10 screens long and you can see it was designed by committee because it’s addressing all these different things and it’s not taking a stand on we are for this persona for this job to be done and not for others at least as our primary it’s not that the others don’t exist but we are clear this is the primary and to be opinionated about that and uh i am a believer that that is actually revenue optimizing rather than saying oh we can help you and you and you and you and you and you for most startups right if you’re salesforce it’s a different thing but if if you’re a startup i think uh not doing that by committee and having the self-discipline because you’re like, yes, I can do all those other things. All those shiny objects, all that money sitting there is interesting. You’ll make even more of it by being focused, in my humble opinion.
Scott Barker:
[23:47] Totally agree. And this is going to be sort of a meta thing with this podcast. So we have ads on the podcast. We work with great sponsors on the podcast. And some of the coaching and learning that we’ve had, when you try to be something to everyone, you’re like, oh, there’s 50,000 people who are going to listen to this. Like tell them we’re the best at everything in the data space or or the engagement space or the enablement space then you don’t resonate with anyone and and then we’re trying to kind of like coach them in like okay you have to know how the market perceives you because the market that you have a reputation you have a brand already and people kind of know that and you might want to be something else but like go to your data and tell us like your best performing customers that absolutely love you and call those people out and just be very real with exactly who you serve how you serve them and when in what scenario are you the best fit to solve that problem and and that can be a tough almost um humbling exercise to do of like okay maybe this is where we want to go but who actually are we right now and who do we best serve right now i’m.
Guy Yalif:
[25:06] Strongly with you and i think the realization that regardless of what you’ve done you do have a brand out there already uh and then your choice is just what you do with that perception uh is is super wise.
Scott Barker:
[25:17] Totally totally um okay continuing down your your journey um you then uh spend two years at Twitter now x uh which is super cool to to have that experience as a head of global product and industry marketing um maybe i’ll switch this question up and instead of kind of what did you maybe get right is there things you did wrong while you were at Twitter now X like if you could go back and and change something about that time period one.
Guy Yalif:
[25:49] Of the funnier ones uh i had the privilege of joining when uh revenue was almost zero and there were 10 or 20 people in the ads business and i was in the ads business three years later when i left around the ito we were at 650 million in revenue and there were 500 people in the ads business.
Scott Barker:
[26:06] I have never been part of growth like that.
Guy Yalif:
[26:10] It was great to be along for that ride and.
Scott Barker:
[26:13] Contribute a very.
Guy Yalif:
[26:14] Very very tiny piece of it.
Scott Barker:
[26:15] So zero to 650 mil in three years and that was.
Guy Yalif:
[26:20] Twitter right i mean.
Scott Barker:
[26:21] Yeah but.
Guy Yalif:
[26:22] In fairness, yes. It’s really different. It’s like, on the base of the company was already 400 people and already, you talk about having a brand already. Uh, um, the biggest challenge we had in the early days of ads was no, we’re not just about what you had for lunch and your pets. Advertisers were like, you have commercial intent here. And we didn’t think that’s what they would be thinking. They made it really clear. That’s what they were thinking. They made it really clear. That’s the brand we had. And we had to lean into our strengths and help them understand, no, there is commercial intent here. You can, and try to shift perception of the brand how.
Scott Barker:
[26:53] Did you go about shifting that so how were what were some of the strategies you used to shift um how the market was perceiving you.
Guy Yalif:
[27:04] Three come to mind um because this was enterprise ads at the time right this wasn’t self-serve SMB yet that was a couple years later um in person literally talking to people uh we also hired a bunch of people who had relationships there you know from agencies from other ad tech companies uh that was part of it a second was, data to be clear hey you know while you perceive you know twitter’s brand perception was that’s what i had for lunch you dear brand you have a brand out there already i’m gonna make it up right five million people mentioned coca-cola yesterday i’m making that up but like they would have been like oh wow i didn’t know that was the case and here are some of the things that they said and so they would say oh okay or you know five million people mentioned pepsi why don’t you go after them Coca-Cola uh or mention something else that you could be adjacent to and the last was um.
Guy Yalif:
[28:02] To help people visualize how they could bring it to life themselves. So some of the most successful work at that stage. Now it’s an old hat. But at that stage, what did we call it? Native advertising was not, it didn’t exist, right? It was either search or display. That was it. Mobile was a kind of advertising back then. And to help people understand, this is how you can use organic and paid together. And bringing stories to life uh the team published a little book of just examples of like insightful tweets witty tweets that i don’t remember oreo did something around the super bowl lights going out like at that time that was manually innovative like you would talk about that at ana masters now that okay that’s old hat but at the time helping people visualize that was really inspirational mm-hmm.
Scott Barker:
[28:54] How did you as um like owning the kind of product marketing function and this ad org is just blowing up. I imagine you saw like do you do you remember roughly how many sellers that were in the ad business like once you start getting closer to the 650 mil.
Guy Yalif:
[29:12] I remember the whole org was 500 i don’t remember how many of those were aes but a big i mean big big big stunk of that uh also had a mid so there was i remember there were three tiers by size of company if memory serves me correctly there were at least two and we had i believe we had SDRs doing demand gen several hundred and globally i i uh like it was a truly global org i had and hired people in san francisco new york sao paulo tokyo london and there were aes and all those places and a whole bunch more wow.
Scott Barker:
[29:50] How did you keep i always think when you go through hyper growth like that one of the hardest things is just disseminating information which is funny the thinking of twitter because that’s kind of what it does allows you to disseminate information quickly but like you have to keep all of these aes um up to date on latest pricing packaging how we’re talking about messaging positioning um how were you able to do that as you’re expanding so so rapidly.
Guy Yalif:
[30:18] Your point, the field enablement part of marketing was a huge amount of work and fortunately uh.
Guy Yalif:
[30:28] The team had huge, incredible goals in front of it. I remember one year, the Super Bowl was perennially the biggest day of the year because you’d get more traffic, so you’d sell more ads. And I remember one Super Bowl, they said, this was great. You should be really excited about this. By the way, Q4 has 90 days in it. We need to do 90 Super Bowls to hit our Q4 number. And so the ramp was just bananas. um fortunately that resulted in in uh that i think that and the sales leadership created a culture where folks really wanted to know they really did care to know uh i’ve worked in other organizations where the sales team was less about that and it was simpler right like when i was at yahoo the surface area of ads they had to sell was enormous at twitter it was really focused at that point in time. Adam Bain, who ran the whole ads business, also was extraordinarily good. I learned a bunch from watching him. Has the org scaled? Where did he invest his time? What did he make himself available for? What level of thing did he begin to delegate? But where did he choose to remain deep? You could talk to him, you know, when we’re at 600 million in revenue, he knew the state of every single very large deal. Every person, every state, every everything. He just had an encyclopedic memory for it he didn’t know that about every single deal but he knew it for every large one while managing overall it was uh is an extraordinary leader.
Scott Barker:
[31:58] Yeah I love that um where okay so you said one where did he choose to spend his time so one was any larger deals he would make sure he knows about them where else would he make sure that he he was involved in.
Guy Yalif:
[32:14] It was watching him, you know. When there were 20 of us, we just got stuff done. When there were 500 of us, there was an EA managing time. There were multiple layers. There were groups doing things separately that he would then go do in all hands and give context on. It was that kind of scaling that I think he did really effectively. And he knew, I think, did a very nice job building the personal connection even when the touch points by necessity became less. Because the org is bigger. I think he was gifted at that, as many sales leaders are.
Scott Barker
[32:54]: Yeah, I love it. Do you have any thoughts, opinions on the evolution of Twitter? Now X and Elon taking over. Any thoughts? I’ve heard it’s doing extremely well.
Guy Yalif:
[33:07] I don’t have any good ones, so I’ll keep them to myself.
Scott Barker:
[33:10] Okay, sounds good. We’ll plead the fifth on that one. All right, so completing the journey, You then go to BrightRoll, which I imagine was kind of this full circle moment because you got acquired by Yahoo, your old company. And then, you know, you go all in and you’ve spent the last nine years building Intellimize and now part of Webflow, which, you know, is an incredibly successful exit. What many founders, you know, aspire to do. Nine years, that’s a long time especially in startup land uh I think that’s it’s kind of like dog years I think so it’s it’s a long time um what was the hardest part of that journey.
Guy Yalif:
[33:55] The first thing that comes to mind is the existential threat dread fight or flight is that felt perpetual didn’t matter how much money we get a 50 million dollars in the bank i still felt existential dread all the time and he, candidly um while i know that it you know it’s a whole bunch of people who are making thoughtful bets in a risky business trying to go make things work i felt it very personally on people betting their careers on this and you know on the executive team the founding team on me and no i know it’s not all about me or the executive team or the founding team at all but i oh i felt that weight a lot uh and and so you know um about all the all the all the the the families when i thought about that existential dread um just just a sense of team and camaraderie and care and responsibility and just just that that weighed on me um uh the the most when you think about hard things and it surprised me the week after the acquisition closed my shoulders like went down a little bit, and I didn’t know they were up. I thought I was at equilibrium, and I didn’t know they were up in that way. And when I reflected on what was it, it was specifically that. There are a whole bunch of other things to think about and worry about at work and push hard on, but that one had changed.
Scott Barker:
[35:22] Yeah, yeah. And thank you for sharing that. I think it’s important to talk about and anytime you’re doing really, really hard things, going after a crazy goal or trying to build a big business that you feel a responsibility to do well because people have believed in you, comes with sacrifice and trade-off. And oftentimes it’s this feeling of great weight and great pressure. If you were to do it again, is that just part of the deal? Are there any ways that you found to combat that along the way? Or is it, unfortunately, just part of the gig?
Guy Yalif:
[36:06] You know, I recognize every person is different. Every person has their own journey.
Guy Yalif:
[36:11] I think for my little journey, it totally is part of the gig. And that uh the antidotes or the at least symptom i wouldn’t say relievers but decreasers are um recognizing that it’s valid to take care of yourself to be kind to yourself uh when uh you know something doesn’t go the way you wanted it to uh if you gave it your all if you did everything you do possibly how to do to find peers to talk to um uh and compare notes with fellow travelers uh um and lastly i think the next time around i sought through that previous experience that we talked about in the beginning that i had a pretty clear point of view and learned along the way hey very few things matter i think even fewer matter next time around uh there were some things that i would be like oh we really need to get that right and you know what i’m not sure we do next time around like it can be the 80 is good enough and i’ve always been a believer, for a long long time that you know perfect is the enemy of good so that wasn’t the problem nor was the problem oh i need to hold on to that i don’t want to let go like that wasn’t it either it was we that like it’s important to get that one right and i think uh i believed that about, more things than i should have even though i believed it about very few things so i think that helps with some of the um the existential dread yeah.
Scott Barker:
[37:39] I like that the focus can be a superpower cutting up the noise company building. In specific let’s say you go and do this again what are the areas you can’t miss at the small few things that you need to get right.
Guy Yalif:
[37:56] I i heard someone say and it’s it it feels very germane he said first-time founders focus on product second-time founders focus on distribution i see you smiling you’ve heard that one before too it’s.
Scott Barker:
[38:10] In our deck baby.
Guy Yalif:
[38:11] It’s like our.
Scott Barker:
[38:15] Our core belief, you know that especially now more than ever with technology moats kind of disappearing it’s easier to build than ever before your last true moat is kind of execution and distribution um for sure so i love i’m a huge fan of that quote.
Guy Yalif:
[38:32] I love tying execution to it where you know I remember early on thinking of ourselves and then watching others be like, I need to keep this idea to myself. And you realize, you don’t because the execution is you know 98 of it in almost every case you don’t need to keep it to yourself uh distribution and then as you said and then um just being relentless on uh product market fit which i think is associated and it gets at that core what’s the problem we’re solving and people um it is absurdly incredibly tempting to make a hire more quickly because by definition if you’re hiring somebody you’re suffering because there’s more work to do so you need to bring on somebody on board and then waiting longer to find the right person makes the suffering even longer i uh waited and did that longer in particular for the executive team a couple members of my board gave me a really hard time about it and uh that i would do again i would i would do again that way but i think those are the very few things that matter yeah.
Scott Barker:
[39:34] I love it um and i believe that uh justin khan quote the ceo founder of twitch so we’ll give him his uh credit where credit is due um and i love it well i gotta ask the kind of the opposite of that question what was the most rewarding part now looking back.
Guy Yalif:
[39:55] The this thing that fed my soul uh wasn’t making a quarter or even a customer getting up on stage and say nice things which i told and believe told the company and believe myself like that’s true north customers saying nice things about us on stage the thing that fed my soul was people, joining and like two weeks later being like thank you you weren’t lying about the culture i can just go and run here and that made me very very happy because i think culture is one of the very few things that flows from the top and to create an environment where people get to do their life’s best work is an incredible privilege and incredibly rewarding hell.
Scott Barker:
[40:38] Yeah absolutely no no better feeling uh than that uh couldn’t couldn’t agree more uh sophie paul and us in this little vancouver office there’s nothing more you know rewarding than you know seeing them just absolutely crush it and love love what they’re doing and just like get get out of the way and let them cook. Let them cook. They’re doing great work. So I love that. All right. I want to quickly go to a founder question as we sort of wrap up. A couple more questions for you. This one’s super interesting and something I’m actually quite curious about myself. There’s been a lot of asks recently from founders in our portfolio. The question is, as a startup founder, what’s the best way to build relationships with PR outlets, reporters, and analysts?
Guy Yalif:
[41:28] I think it begins with, using your targets thoughtfully uh you know are are it’s going to be rare that you’re big enough to be general business like wall street journal stances are much better you should focus on industry specific folks then is it your customers industry is it your industry and then to think okay well i probably can’t get the very top tier to begin maybe you can maybe you’ve got the relationships maybe you can’t uh one two to very much look at it as a long-term relationship just like with investors right not transactional and to the extent you can be a resource for them recognize that their time is incredibly valuable um but try to be helpful every interaction you have three recognize what’s newsworthy to you is almost certainly not equal to what’s newsworthy them um because they have a zillion other founders talking about their fundraising there was one point where we raised money and i figured who it was maybe maybe it was tech crunch maybe it was venture beat maybe it was the journal someone was like unless it’s a hundred million dollars like we don’t want to cover it right now i’m like great that’s your bar right now um you know chances are very low your feature individual feature launches are newsworthy um or.
Scott Barker:
[42:41] Your new integration probably not, yeah.
Guy Yalif:
[42:44] Yes uh and so and and and to like then make it more newsworthy by doing your homework like really fully read what they wrote read their hypotheses in market does that align with some of the stories you want to tell in market so that there is a fit there and when you do that then be super clear as you’re preparing to talk with them and talking with them what do you want to say have it down to two to three points that you want to make sure they remember that ideally that message gets pulled through and then have ready in my humble opinion plenty of reactive Q&A in case they take you down other areas and be also really clear about areas you’re not going to go, like like we did not want to talk about uh the ethics of ai we have a point of view but that’s not what the company’s about it wouldn’t help the company’s brand to go there uh and then practice, bridging from one thing to another or deflecting entirely where you’re like i don’t want to talk about that thing and the last thing that comes to mind is um if you don’t have the relationships uh find a good agency that does uh and and in my humble opinion good equals.
Guy Yalif:
[43:52] You can see that they’ve worked with this reporter a bunch or this author a bunch. And they can tell you, they have a point of view at your level of sophistication, right? If you’re a PR pro, then they’re talking to you there. If you’re PR new, they’re talking to you there about what this individual needs to see. It’s a bunch of things, but I think it’s a real effort. It’s not like, I don’t think it’s worth doing it lightly. I think you either go all in and make this an investment or not. Otherwise, you’re sort of yelling into the wind. How does all that land for you?
Scott Barker:
[44:25] I think it’s fantastic advice. Yeah, one of my recent learnings is just how relationship-based it truly is. I think there’s, for maybe a while, or people just got disoriented, or it’s not quite the right word, but it seemed like it was more pay-to-play than it is. And I’m learning these are long-term relationships that you have to build, particularly with analysts and reporters. And I think your advice of, okay, you can have aspirational outlets, but why don’t you start with very industry-specific, could be communities, could be small, even like newsletters. Sometimes there’s highly influential people that your buyers look to that could act as sort of a V1 PR for you for these different releases that you have. So that’s good stuff. Final two questions. And they’re always the same. I keep them intentionally vague. So you can highlight something we already talked about or do something totally new. First question is, what is one widely held belief that founders hold to be true today that you think is bullshit or no longer serving us?
Guy Yalif:
[45:40] I think that you have to say goodbye to your friends and family for five years to start a startup. It’s just not true. I actually think it produces worse business outcomes. And I say this as someone who, my first startup, TradeWeave, where I was employee one, was .com one, and I actually tracked my time because it helps me allocate it in the right place. I averaged 80 hours a week for a couple of years, peaking at 135. That’s not the screwing around time. That’s like work work. Total self-actualization. It was incredible. I think I get more done and get a lot more done at Intellimize. I still work well over 40 hours a week, but it’s not like that. I know my wife, I know my two daughters well, and I’m in their lives regularly. And I think getting a full night’s rest, which I measure with this, which is an aura ring, like that feedback loop, I think causes me to make a bunch of better decisions. Maybe I ran more steps in those 80 hours, but the percentage of time that I was like, oh crud, I didn’t need to run those steps at all, I’m headed in the wrong direction, was so much higher then than now, I do think that that belief is just not right.
Scott Barker:
[46:54] Yeah. I wonder if there’s a bit of learnings from… I think it’s awesome that you track your time 135 hours a week. It’s insane, by the way. But I imagine, and this is probably good advice for a lot of the founders listening, is you tracking your time, I bet you could see what times you were most effective. What areas you were working on in the business that produced the outcomes you wanted. And then like over time, I imagine that it just made you more efficient with what you were spending your time on too.
Guy Yalif:
[47:28] It was very helpful. And the notion of tracking your time sounds incredibly burdensome and like a lot of overhead. And I found a way, if anyone else does, I’d like to find a way that’s right for you that takes no cognitive load, feels automatic. And don’t care about accuracy. The point is not to be accurate to the minute. The point is to know the overall trends. And I found it particularly useful as a founder because the job sometimes is whatever needs doing. And so the needs would shift so dramatically week on week. And so I’d say to myself, oh, I needed to spend 40% of this week on recruiting. Did I? No. Oh, I need to spend 40% of the week helping the sales team. Did I? No. And to like have that intellectual integrity and feedback loop was… Was really, really valuable. And then for knowing during the day, I must admit the ring was really helpful there where it could quantitatively tell you, you’ve got more energy at this time of day and less at this time of day. And so I do more strategic thinking here and more rote execution here.
Scott Barker:
[48:32] I love it. Great, great advice. I think I got to get one of those aura rings. I’ve seen them on too many people and everyone seems to love them. So I think it might be a holiday purchase for me. Final question, and thank you for spending the time, Guy. I’ve really, really enjoyed this conversation. The final question is sort of the silver bullet question. Everyone’s looking for things they can implement today that are actually working. What is one go-to-market tactic strategy that is actively working for you today at Telamize and Webflow?
Guy Yalif:
[49:07] A whole bunch that were working to drive demand are not anymore right now, and that changes all the time. One thing that we are finding helpful is small group events, dinners with senior people where we’re not pitching, where we are creating a community for them to connect. And often afterwards, they’d be like, I expected you to pitch me. Can I learn a little bit more about that? We have found a good use of time. And I don’t know of any silver bullets. If you know of one, please share.
Scott Barker:
[49:41] I love it. Well, the executive dinners, no pitch, is as close to my silver bullet as well. It worked super well for us at Outreach. It works at the fund, works for our partners.
Guy Yalif:
[49:54] It’s incredible you are doing it at the fund. Those are amazing events.
Scott Barker:
[49:57] Thank you. Thank you. Yeah, and they’re awesome. Just everyone wins. The attendees get to learn and network, and sponsors get to build new connections, and we get to talk to our LPs and our founders. So yeah, definitely bake that into your 2025 marketing strategy if it’s not already. You can partner with people, you can bring costs down. They can be incredibly efficient, a kind of marketing spend. Anyway, Guy, you’re the man. Thank you so much for sharing your wisdom. You’ve had such an incredible career, and it was great to get to spend some time and kind of dissect it with you. If people want to follow your journey, want to get in touch, are you an ex-guy from your time at Twitter? LinkedIn, what’s the best way to follow your journey and see what might be coming next?
Guy Yalif:
[50:45] Would love to connect on LinkedIn. That is a great place to get together and continue the conversation. And Scott, thanks for having me. It’s an awesome conversation. I enjoyed it a bunch.
Scott Barker:
[50:55] Amazing. Well, I appreciate you. And to all our listeners, thanks for tuning in this week. I say it every week, but now listening is one thing, executing something totally different. Hopefully it gave you some ideas, tactics, strategies that you can implement into your own organization. and we’ll see you all next week.
The post GTM 126: Reverse Engineering the Founder Journey: From Scaling Twitter Ads to $650M, 20 Years Operating, and a Webflow Acquisition | Guy Yalif appeared first on GTMnow.