Inside marketing at Stripe, OpenAI and Retool | Krithika Muthukumar (VP of Marketing at OpenAI, ex-Stripe, Retool, Dropbox, Google)

Brett: Well, thank you for joining us.

Krithika: I'm very happy to be here.

Brett: An interesting place to start would be telling the story about how you got involved with Stripe and maybe what, if you can recall all the way back that, like, what did the first few months actually look like?

Krithika: So this was in late 2013 and I'd gotten an intro to the Stripes founders from a colleague of mine. his now wife worked at Stripe, Christina Cordova. And my first conversation with the founders was, uh, well with John specifically was telling them that they had done all of their websites wrong.

Krithika: And he asked me to critique a recent landing page they'd put up about Stripe Connect, the very first early version of that. Which is the transfers API. And yeah, I went through it and I gave him some unvarnished feedback and I think he quite liked that. And I convinced them that they needed a marketer.

Krithika: They hadn't had a marketer until then and convinced them that they needed someone to think about marketing as a discipline full time. so I joined in, in late 2013, the first couple of months, It was a crazy velocity place. Like we were launching things left and right. And I remember the very first launch that I worked on was the launch of multi currency support. And even then, like before I started at Stripe, I already knew it was kind of special, right? In the conversations that I had with the founders, they had never done marketing before, but they already felt like they were 10 steps ahead of me. They had all of the right instincts. They were thinking about brand from day one. And I knew what I could do is kind of come in and help polish and amplify the work that they were doing. But I wasn't going to revolutionize or change the way that Stripe wanted to do marketing or the DNA of Stripe's brand and marketing in the world. but this multi currency launch, kind of going back to that first launch that I was a part of at the company, it already felt like, you know, Stripe was this very integrated product marketing, go to market comms machine, because The way that the product was architected was so deeply understanding the developer pain point at the time. And so it made product marketing almost fairly trivial, if you will, like we were listening to the customers and we were launching exactly what they were asking for. And we were going above and beyond to make that developer experience as seamless as possible. To me. you. know, the value that I was adding was thinking about this as, a discipline, like thinking about it on how can we build on top of that? What new channels did we have to create? Like at the time, things would launch from Stripe and if they remember to, they would write a blog post. There was no email at the time. We weren't really using social media to any good effect. And so the second chapter of my time at Stripe was really about expanding what launches meant. It was about bringing that discipline to. Okay. a launch, a product launch isn't complete until we tell our customers about it. So the marketing of it, the actual communication of the launch became part and parcel of the launch process at the company. And we expanded the channels. We started experimenting with events, with, online channels, with email and so on and so forth to really try to amplify as much as we could what we were putting out for customers. And then we became a much more intentional and that kind of gets into the future chapters. 

Brett: How did you think about if you were doing a good job?

Krithika: In the beginning, I'll be honest, it was about keeping up with the pace and the velocity of the product organization. we were shipping more than a hundred features a year, uh, even in the early days of Stripe. And so part of it was like, are we doing a good enough job explaining what we are launching to our customers so that they're taking advantage of it? Marketing though, can kind of get bogged down in these vanity metrics. You know, you kind of take a look at the number of people who engage with a tweet or the number of people who land on a landing page, number of people who open an email. And I really think those are all bullshit metrics. And really what I've tried to do in the entirety of my career is really focus a lot more downstream when it's in partnership with sales.

Krithika: We actually take a look at revenue that is influenced. And when we work with product, we're looking at engagement with usage of the product. And so success, especially in the product marketing domain, was around product usage and engagement. like, we would report out on the numbers, we would keep an eye on the top of funnel numbers. It's really about that downstream intent of the product line 

Brett: How did you think about the topic of brand? I think, you know, immediately when you talk about the topic of brand, there's a lot of people that want to quantify it um, going back to sort of revenue and product usage, but it's one of those things that is very hard to quantify. And I think if you look at payment processing over the past 15 years, Stripe more than any other company has probably leverage brand and created enterprise value through brand, maybe better than anyone else in the world. So how did you think about like the broad topic of brand and taste and sort of those type of things as the first person in that seat?

Krithika: Yeah, I mean, In many ways, brand is something that has set apart Stripe in the past decade and a half. And a big part of that was truly like a million different decisions that happened. You know, brand can be seen as this very like tops down umbrella where you're going to come up with the brand positioning and messaging and voice.

Krithika: And then that cascades down into all of the activities that you do. But I actually think brand, especially at tech companies and at high tech companies, which are targeting developers is a very bottoms up motion where you're making a million different small decisions and being very intentional about them. And that adds up to a gestalt of how developers think about you and then overall how decision makers think about you. So to me, when it came to brand, it was probably one of three pillars that we thought about one was how do we show up for the audiences that we really care about? And so for us, that North star was developers. If we didn't have the hearts and minds of developers and we weren't the de facto for developers, we were going to lose. If we weren't the de facto for startups and we weren't on the right side of switching costs, like people weren't starting on Stripe, getting them to switch to Stripe was much harder.

Krithika: And so how do you make sure that technical founder already knows about Stripe, cares about Stripe, is excited about using Stripe at their next company? That was one, which is like really honing in on the audience and making sure that we were meeting them very authentically. And so that meant kind of stripping out anything fluffy from our marketing, really thinking through, you know, the right ways to reach them that wouldn't alienate developers.

Krithika: So if we put out content, it wasn't behind a gate wall where you had to put in your email address. If we had a campaign that we were running or like a brand campaign that we were running, we were very intentional about making sure that we were using very plain spoken language that would resonate with developers.

Krithika: It wasn't fluffy or over the top. And a lot of it was just knowledge sharing for the sake of it. Our engineering blog got a lot of traction because we were taking learnings as developers ourselves and then putting that out there. second part of the brand to me was, really about consistency. And I think people really undervalue that in marketing. You know, sometimes when you think about SaaS companies that have different practitioners versus different decision makers, you kind of think that you have to bifurcate what that brand shows up like in different channels and at different events and for different kind of personas. I think that consistency actually really mattered for Stripe.

Krithika: You know, we put out a, a primer on machine learning for fraud prevention. And of course you would think the intended audience for that was an engineer or a developer or an engineering manager, even a CTO. And actually the feedback that we got after we put that out was. From all over the spectrum of roles and leaders within the company.

Krithika: So we had a CFO reach out to say, Hey, this is really the most concise way that I have ever heard about, you know, kind of applying the concept of machine learning and AI to the domain of fraud prevention, and it accelerated the deal where the CFO was the final decision maker for bringing in Stripe into their very large, uh, enterprise organization.

Krithika: So I think that consistency, you know, when you think like, Oh, you need a different message for CFOs, a different message for IC engineers, I think that can actually kind of lead you astray when it comes to brand development. So that consistency is really key. And even that developer centricity was something that got. Larger companies excited about us. You know, the only reason that PNG was having a conversation with Stripe back in the early 2010s was because Dollar Shave Club at the time was eating their lunch. And so they were trying to figure out, Oh, what are, what are all the things that Dollar Shave Club is doing differently than we are? And of course, some of the technologies that they were using, including Stripe was one of the reasons that these enterprises also kind of take a look. So that consistency is the second pillar. And I think the third pillar, well, let me just be plain spoken.

Krithika: It was, it was copying from people who were doing things well, but very much from outside of our discipline and from our domain. And so we would never try to one up our competitors. I actually think like keeping too close of an eye on your competitors. leads to local maximization rather than thinking about like the global phase shift changes that you could be making. But we would steal copiously from domains as far ranging as healthcare to people who were launching new programming languages. to things like the security field. You know, we launched a Capture the Flag tournament at Stripe, and that's typically for, you know, InfoSec researchers and Black Hat type of, areas of, of security research. And we did that in the payments domain, and we had no expectations of how many developers would participate, but at its peak, we had about 10000 people go through the entire five different levels of the Capture the Flag challenge. And many of them, actually, many of the victors turned into Stripe engineers in the future.

Krithika: So that kind of stuff would be really interesting to our brand as well. 

Brett: What are other examples of, of areas outside of payments that you took inspiration from

Krithika: Yeah. One was, when we launched Stripe Sigma, which was our data analysis tool, where you can kind of go in and slice and dice your Stripe data and revenue data. we took a lot of inspiration actually from a new programming language that had launched around the same time and the way that they showed sort of examples and different code snippets of how to build in that programming language. and even the interactivity of how they put together their documentation was something that looked very similar to the initial landing page that we put out with Stripe Sigma. And, I think we got a lot of credit for it, but I actually want to now give credit to the folks who did it with the programming language.

Krithika: But yeah, if we had gone in and copied stuff from our competitors at the time, I think it would have just been, pedestrian and, and kind of minimizing to what otherwise could be possible with the brand.

Brett: As you started to have more resources, how did you think about resource allocation as it relates to brand? in the marketing domain, it might be, you know, if you do a webinar, it's easy to sort of start to see how that leads to revenue or usage or marketing qualified leads or sort of those types of things.

Brett: It obviously is very different in brand. And you all did things like you can quantify the cost. You launched Stripe Press, which I would view as a brand enhancing marketing initiative. Maybe you thought about it differently. But also, everything you did from a design perspective, like everything had to have been more expensive or a lot of it.

Brett: Where you could have taken that money and done all sorts of other stuff. Grown the sales team done tons and tons of things on a marginal dollar basis. so I'm curious. Maybe early on, and then as resources grew as like a capital allocator, how did you think about brand?

Krithika: That's such an astute question. And it's going to probably going to be a meandering answer because there's so many different parts of it to unpack. the first and foremost thing is that brand isn't owed by marketing. Like I would be lying if I said that. And I also think it's disingenuous and probably like detrimental to how you think about brand in a company.

Krithika: If you think marketing owns it. brand is a shared cloud between marketing, between comms and PR, between the founders themselves, the product, like the brand is sort of the first touch point into the product. So, I think if you think about it with that ethos and for example, Stripe Press was an organization outside of marketing when it first started, we incubated it as a program that was really more mission driven, you know, Stripe's longterm goals, we re around increasing the GDP of the internet.

Krithika: And in order to do so, we were investing in the best world class developer tools. We were also investing in sharing knowledge, and sharing some of these ideas for progress with the world. And so I think if you do brand bets that are too orthogonal to your mission, And they aren't tied in that way. I think people can very easily sniff that out.

Krithika: And so one of the reasons that Stripe Press works and you know, there are so many people who have been kind of copied that effort with an editorial arm of their own is because then it doesn't ladder up to their mission or their long term orientedness as a company. So I think one of those things is really important. The second thread that I would pull on is You know, with brand, I think of it as like the business value of delight. And the way that I justify it is, let me try to make a concrete example. So we launched a page at Stripe that showcased our open source contributions. And this open source page was just like a collection of different libraries that we had put on GitHub, different tools and services and little utilities. we delayed the launch of that page by almost a month and a half because our design team wanted to implement the game of life in the background, in the header background of that page. And that sounds crazy. It's like, why would you delay the launch of that by six weeks? But. What happened was it went viral, like the design community took a look at that page because they saw that interesting kind of animation in the background. The developer community took a look at it and saw the craftsmanship and the, importance that we placed on the design and the aesthetics of the page. And I think it speaks a lot to then the craftsmanship that we place on our product. There's almost like this. this attribution that is imbued into your product by how much time and effort and, initiative you place on your marketing.

Krithika: So I think that is something that has carried through with me, not just from Stripe, but in my other chapters as well. You know, at Retool, we put out these beautiful explainers about the history of visual basic, about the history of Yahoo pipes, which are sort of spiritual predecessors to, to Retool. And we spent a lot of time kind of coding in some Easter eggs and design elements that then caught the attention, the hearts and minds of developers and the people that we wanted to be reading the page, including designers.

Krithika: So I think what it can do is like when you spend that extra time and craft. increases the ability for you to reach audiences beyond that very core ICP that you care about. People take notice when people pay attention to the detail of their domain and their discipline. So that is one part of this like business value of delight is that you get this association very early on in your experience with the brand. That it is a brand that cares about craftsmanship, about detail, and you kind of imbue those attributes to the product experience you may eventually have with the brand as well. So those to me are kind of important. When I think about like the capital allocation, as you said, the framework there, I'm not a pioneer here by any means, but, you know, Jale at Mutiny has talked a lot about. Program level CAC. And I think that's really important that you kind of think about blended CAC, overall across your marketing activities, but that you also think about it at the program level so that you're not just sort of thinking about, Oh, you know, this became more expensive because we thought about it from the brand perspective, or we invested in brand. But you can either amortize that across the rest of your programs or think about it as, you know, what is the program level, return that you're getting and then kind of keep brand separate. I really think brand is always a little bit of a bet and your founders have to be bought into it. the rest of your leadership team has to be bought into it because if you're always looking at the short term payback from brand, you're not going to get there.

Krithika: But in the longterm, it kind of amortizes across all of your programs. It makes them all a little bit more effective. And, I think it pays off a lot of dividends. I'm a big believer. 

Brett: One sort of the interlinking concepts or related concepts to brand is sort of taste. I'm interested in getting your thoughts on how you sort of started to scale taste, maybe across the company, but specifically in marketing. 

Krithika: be a little contrarian there in that I don't think we did at Stripe. And what I mean by that is, we instead invested in processes and systems that ensured that everything that went out the door had taste. and so we came up with a fairly simple system. You know, we would do a 20 percent strategy review to make sure that we were aligned on the goals, the outcomes, the sort of intent of any big project or work stream. Then we would do an 80 percent review for the execution, like how are things going? What are each of the channels looking like? What is the collateral looking like? And I think it's kind of important that you do it the 80 percent mark, not the 99 percent mark because you still want the ability to make changes based on that. But it does mean that the person responsible for the WorkStreamer initiative has kind of gone and done a bunch of the homework, a bunch of the work required for us to see what it's going to look like in action. And then we would have these marketing review forums. Where not only the team that was reviewing their work stream was showing up and that was a forum where John, our co founder was present, our marketing leadership was present. We would also have sort of a shadow zoom room, like a marketing fishbowl where the rest of the marketing organization could see the discussion in absent and that transparency went a long way to kind of helping others see, you know, what they should be thinking about when they are coming to these forums.

Krithika: What are some of the kind of thematic areas that are called upon, discussed upon, But the reality is there were some people who had the red pen and we had these reviewers that were kind of deemed across the organization where they were putting on the hat of the user and saying, Hey, if I'm a naive user, who's seeing this piece of collateral for the first time, am I confused?

Krithika: What questions do I have? Uh, does this make sense? Is it in line with the Stripe branded toad in terms of consistency? So those mechanisms were the thing that made these things possible versus saying that everyone just went through a course or an onboarding week where they suddenly picked up the same taste as the rest of the organization.

Brett: were the people with the red, was that an explicit designation?

Krithika: It was, yeah, there were, five or so when we first started and there were sort of domain area experts, and then I think that program has scaled or changed quite a bit since I've left.

Brett: And those people would review basically absolutely everything before it went out to the world.

Krithika: every piece of content. So if it was, you know, touching an audience size of less than 100 or so users, we would expect you to just get a peer to take a look at it to make sure that we didn't have any grammatical errors, but anything above that, it went through that review process.

Brett: What did the, those actual marketing review meetings look and sound like, maybe the 20 percent and the 80 percent?

Krithika: They would span the gamut. You know, sometimes it would be a very quick, like, yep, this looks good. Let's get it out the door sort of situation. the 20 percent mark was usually, you know, people would come in with a pre read. We would spend some time reading through the document, writing up some comments, marking things for live discussion. these things were pretty well interrogated in order to make sure that they were robust, right? The intent behind it was not to poke holes in the strategy. The intent behind it was to make sure that we were aligned up front so that we weren't randomizing the working team towards the end of the project. That's sort of what I see often happen at scaling startups is that everything is sort of like in the head of the founders or in the head of the one, you know, early marketer who knows everything. And by the time a new person comes in, they don't quite know how to succeed. Like too much of it relies on social capital. So these systems and processes was, really meant so that a marketer in their very first month at Stripe would know exactly what it took to take something all the way from idea to execution and was able to follow a series of processes in order To make sure their work was very effective at the company. So again, sometimes it would be very much around like the creative ideas and what these things should look like, you know, bringing in some inspiration from other companies. Sometimes it was about, asking, is this really the right audience? Is this really the right positioning that we want to get on other things?

Krithika: where around product goals, sometimes you would kind of get into the realm of Is this the right product direction if we're marketing it in this way, or we're constrained to market it in this way? Should we not be making some changes upstream to what we're launching in the first place? So, Again, they could really span the gamut depending on what we were talking about.

Brett: Was there anything that you did to sort of manage against the dynamic that someone might feel micromanaged or their sort of autonomy was taken away? My guess is in some of these meetings, the altitude would drop very low and someone would be workshopping three sentences at the end or something like that.

Krithika: I think that is always the failure mode. And so some of the guardrails that we put against that is that everyone who held a red pen, for example, we made sure that by the time that they were putting on that hat, it was really about consistency and about, making sure that we were putting ourselves in our user's shoes, especially those naive users seeing the messaging for the very first time. And it was less about, you know, that subjectivity versus. thinking through, okay, is this objectively meeting our style guides? Is it objectively confusing or not confusing? And how do we get it there? So it was about improving the work rather than questioning the strategy. And I think that was really important because again, you are in it, you're in the trenches along with your working group until the very end.

Krithika: And at some point you kind of put on that reviewer hat because it is about, you know, every touch point, every email, every blog post, every landing page. Is a representation of our brand, every event and talk that we give is a representation of our brand. So the importance of that in the organization kind of manifested it in that way. The second thing is, you know, we provide a lot of guardrails and documentation in terms of what to expect from these meetings, what to bring to these meetings. And so if anyone was ever kind of going off into a tangent, one of the things that our COO at the time, Claire, would say is, um, You're not just point out the elephant in the room or acknowledge the elephant in the room, but hug the elephant in the room. And so that was something that was sort of a mandate to the entire organization is that if someone was rabbit holing on something, or it wasn't a productive use of the time. It was always fine to hug the elephant and say, Hey, I think this isn't a productive use of this forum. Why don't we kind of go back to the decisions that need to be made? So again, yeah, like the failure modes always could possibly exist, but, I think we had enough guardrails to support against it. I would say on this point of like micromanagement, I maybe have a contrarian point of view in that. I don't think good brands are made without micromanagement and I think micromanagement gets a really bad rap and it's not about giving people independence or autonomy. It is about really putting your user first and putting the customer first. It's less about any individual in the organization. It is it's more about the merit of the idea and it's about making sure that the user experience is as best as it can be. And it does take a little bit of the funnel tightening to a certain set of people who kind of understand that in order for you to maintain that bar and consistency. I think some of the best brands in the world have had those kinds of, scenarios like, Steve Jobs at Apple, for example, or, you know, the founders at linear care so much about everything that goes out the door, I think there is a commonality there. It can still be a very kind environment, which is how I would paint Stripe.

Brett: I think sort of watching the company at afar, one of the interesting dynamics that we were touching on is brand and marketing were actually an area of strength of Patrick and John's. I think conventionally, most great founders tend to be technical or product spiked sort of type founders, and I think there's a lot of advice for when you're the first product hire and the founder and CEOs sort of spike is product, and sort of how do you manage that? I'd be kind of interested in getting your perspective. If a friend of yours was specifically joining a company. Where the founder was opinionated and had great taste and sensibilities and interest in marketing. Is there anything different that they need to do relative to someone joining a company when the founder and CEO, this isn't sort of an area of expertise or interest?

Krithika: yeah, first of all, if the founder has an opinion and is excited to lean into marketing, that is a gift. it is actually fairly rare for, you know, founders to want to care about the go to market, want to care about the positioning and messaging, want to care about the brand and really invest there. And so. To me, that was always a blessing. And so the way that I would engage with them was much more about extracting their opinions, providing an a la carte menu of options and trying to get to the ground truth of what they wanted to do with the brand.

Krithika: if I had to be like kind of break it down as advice, if your founder is someone who is excited to lead into marketing, give them a lot of homework and reading and inspiration of how other people do it. Uh, I think kind of showcasing examples and showcasing the option space is really helpful to kind of help hone in the founder to what they want, because they might have a very kind of crisp understanding of what they want the brand to show up as, but they might also have a very loose and big understanding of what they want the brand to show up like. So if you want to just sort of hone in on an approach and to move very tactically ahead on those work streams, paint them a menu of options. And then for the founders who seem to not care as much about marketing or do not want to lean in as much, it's your job to be an advocate to help them understand the benefit of it. And so kind of showcasing again, you know, companies that are doing it well and what it takes behind the scenes, like what investment and what commitment does it take from the founders. what inputs and what kind of time does it take from the founders to make that happen? I think that storytelling can really help. And then of course, showing early wins in marketing, showing the impact of it can sort of naturally cause people to come more into the orbit of that world. Uh, again, if, if they're leaning in, that's a gift.

Brett: What else would you share with somebody that's going in as the first marketing hire? You know, somebody is an experienced marketer, but this is like their first time it's 25 people.

Brett: Maybe it's the first million or two in ARR that you would sort of, if you had a handful of minutes with them to sort of say, Hey, watch out for this or think about this what's sort of your go to. 

Krithika: Look, like it does depend on the sort of nature of the funnel of the company. So if it was a very inbound company versus a very outbound motion, a sales driven motion, my advice would probably be a little bit different, but I think the commonalities across them is really understand the sales or buying motion, whether it's. Product led or self serve or sold, and I really understand the dynamics of the funnel really deeply. Almost like a homework assignment I would provide is after the first month, you should be able to create sort of a, a state of the funnel report that you're sharing out with the rest of the leadership team in terms of your observations on where the biggest drop offs are, where the biggest opportunity areas are.

Krithika: So you're sitting with the product team, you're sitting with the sales team if needed. You're sitting with the data science team, if, if one exists, or the CTO themselves to kind of spelunk into the data and to put that report together. Cause that really grounds your understanding in sort of how is the mechanics of the business operating today and where the opportunity areas are. The second is go deep with the customers. I think there is no excuse for you not directly to be talking to customers. And nowadays with gong, it's very easy to be sort of fly on the wall for any sales conversation. And so really understanding the customer pain points, the use cases directly from the customer's mouth is going to be extremely important to you as a marketer. And then the third is, do something hands on. I think marketing leaders often kind of feel, that they need to kind of take a step back, listen to the organization, take a long time before they can start contributing. But actually like being a part of the launch, a launch in the first 30 to 45 days is an extremely good forcing function to kind of understand the operational dynamics, the people, and like sort of the who's who in the organization and who actually get things done. who speaks. At the problem versus who does something about the problem. How do you actually like publish something on the blog? You know, what does it take in order to get something like that done? Where do you get the data for the user list and the customers that you're trying to email? So even as a leader, I think you should get pretty hands on to understand the dynamics of operating a launch at the company so that You can improve those things or, you know, you can get hands on when needed. so those would be my three, like really understand the business dynamics, the funnel dynamics second, like get really deep with the customers and the pain points there, because anyone who's been at a startup, especially a hyper growth startup for more than three months, kind of gets a little bit inured to that as you're in that go the next thing, the next shiny object mentality. And then the final piece is like. Get hands on a launch so that you can understand what it takes to actually drive process at the organization.

Brett: Maybe sort of building on the last point. How would you think about prioritization? You know, as that first month, there could be an endless list of things that you could spend time on.

Krithika: Yeah, I mean I was the first marketing hire at Stripe when it was 60 people and so I saw it all the way through to around 7500 people and in each chapter there was a different set of priorities. But in those early days, especially the first three years, I was the only marketer there, you know, every day was a constant exercise in prioritization.

Krithika: Do I work on a sales narrative that's going to be used for the next year by every single salesperson? Do I work on a blog post that needs to go out the next day? Do I work on, you know, ICP and, and buyer journey research so that we can get a little bit more crisp and articulated on who we're targeting and why, competitive research and dynamics.

Krithika: So again, like the possibility space was endless in terms of what I could be doing. So when I advise startups now, what I suggest is that the job of the marketer, especially at the beginning, but actually on a constant basis is that of diagnostician. You really need to kind of dial into. What are the needs of the org today?

Krithika: Right now? maybe the horizon that you can take a look at is like the next three months, maybe the next six months. But at a hyper growth startup, probably just the next three months. And what you want to do as a diagnostician is to understand again, what's the health of the funnel? You know, are we weak at the top of the funnel?

Krithika: And so do we need to do more demand gen there? are we weak at converting customers with intent into actual purchasers? and so do we need to work on that middle of funnel content is whether it's like sales narratives or customer case studies or ROI calculators or whatever else it might be, or is retention the problem we're throwing a bunch of people in at the top and then it's just a leaky funnel at the bottom. What are we doing to keep people on? What are their biggest pain points? What's causing them to leave? And so depending on your answer to that diagnostic question. You may invest in very different hires. You may invest in very different work streams and different strategies that you might employ.

Brett: And so you sort of are constantly doing this diagnostic and you're basically trying to figure out like inputs and outputs and on a marginal effort basis, what's going to have the biggest impact.

Krithika: That's exactly right. And especially in the early days, you want to bring on folks that are well rounded, you know, these T shaped marketers that may have a domain discipline area that they're experts in, whether it's product marketing or demand marketing content, but can flex to other needs. Like, I think if you bring in highly specialized folks into a startup, they're It often doesn't work out because your diagnostic may yield a very different result three months from now than it does today.

Brett: Maybe you could kind of bring it to life. We didn't talk a lot about Retool yet, but it's a more recent experience. Like what can you talk about, like when you were doing a diagnostic, when you just joined, what that looks like and how it translated to what actions you choose to, you chose to take?

Krithika: Yeah, for sure. At Retool we had a very different dynamic than at Stripe. You know, Stripe was a, an inbound behemoth. Like when I turned on the contact sales form at Stripe, I had to turn it off because we had so much inbound demand come in that We didn't know what to do with it. And of course, that's a good problem to have. still a problem because then we had to go figure out lead routing and lead scoring and hiring up our first, uh, accountant managers and SDRs and so on. which we did, but you know, a very different game than at retool where we had tremendous product market fit, like huge enterprises were using the product. for very deep, internal tools. and business software. But the challenge with retool was that we didn't have that sort of word of mouth concept, right? Like we didn't have a virality to the product. And so we had to really figure out outbound and bringing in more demand at the top of the funnel. great product market fit, just not enough people knowing about it, not enough awareness of it. And so, one of my first leadership hires was a demand leader because we wanted to build out these programmatic engines that would be very predictable over time. So We went from like one very nascent engine, which was paid search for us, um, you know, branded keywords where we were capturing interest for retool to eight different demand engines, whether they were things like a webinar program or even investing in trade shows, which I feel a little strange saying as a developer marketer and a former developer myself, but you know, I let the data speak for itself and trade shows were a great ROI positive, channel for us. We did, invest in things like conversion rate optimization, CRO, uh, SEO, and then, paid social account based marketing and so on and so forth. But like all of these different engines that then added up to predictable demand that helped us hit our numbers every single quarter. So again, the diagnostic was very different because the goal of the organization was to scale the revenue side of the business. Though we have like very strong product market fit. It wasn't about like a plethora of launches. you know, we had strong product marketing in place, but we didn't have was a demand side of the house. So that's where we invested.

Brett: What are your thoughts on the difference between Marketing to mid market or SMBs versus enterprise. There's been a lot that's been shared around sales motions and how different it is if you're selling a 10 K ACV deal versus a million dollar deal. But outside of maybe marketing supporting sales collateral,

Brett: I don't think there's a lot of. knowledge about the difference between marketing when the end deal size is 500k or a million versus 5k or 10k.

Krithika: Yeah. I mean, taking a zoom back, if you are doing both those segments at the company, like you are selling both to the very low end of the mid market and to the very highest end of the fortune 500, I think you probably want to get out of the business of very hands on sales at the low end. And so less of a marketing question and more of a go to market question, but I think you want to make that a self service possible.

Krithika: So actually at retool, we did a very counterintuitive thing where we nuked a big part of our sales lead volume. By launching a self serve enterprise plan, and so the thing that people would have to contact sales for, which are things like, you know, getting SSO and a few other enterprisey features, uh, and on prem, for example, was something that was gated behind a sales wall for retool, we actually ended up putting in our self serve product, and that was a big controversial decision that we made because it would siphon away potential interest in sales conversations and move them into self serve. Well, we did that because we wanted more focus and prioritization for the sales team to be able to move more up market and to focus on larger layouts and more wall to wall engagements. So I think one, the precursor to anything that marketing can do on the enterprise side is focused from the organization to allow the sales team to be able to thrive rather than being bifurcated and split across multiple different segments. that are maybe Quite demanding on your time, but nowhere near the ACV or value for the businesses you might need. You may still want like an assist motion at that lower end, but anyway, I digress. On the enterprise side, a couple of things that are really key. I think one is starting to get to verticals and to solutions.

Krithika: So being able to sell to enterprises at that level it's much less about your product and your capabilities and much more about the benefit that you're bringing to their organization. So. You really want to extract first the value drivers, the things that exist outside of your product existing in the world, that these enterprises are going after.

Krithika: So at retool, for example, some of the things that we really thought were value drivers was. One, the ability to reduce risk. So having an internal tool that is not very secure, that gives any employee access to able to fact figure a database and drop customer records. Like that's a huge source of risk. Whether or not Retool is available in the market, customers care about reducing the risk of their internal systems. The second is like moving faster, like getting to market faster. So, uh, some of these companies, you know, when they launch a new pilot or a new beta, uh, oftentimes they forget about empowering the sales team, empowering the support team, uh, who's actually going in and, you know, changing things for a customer if they need to versus having to go bug the product engineers for everything that needs to happen in production. So those kinds of things, these value drivers, Can lead to solutions that are much more verticalized. So we got to these patterns of success to say, if you're in the e commerce world, here are a set of business software that you all need to build internally. And here's how we would very opinionatedly tell you to go and create your roadmap around them. Same thing. If you're in SaaS or if you're in financial services or in healthcare, we had a playbook, uh, a blueprint for each of those segments. Then you go get the reference customers, those lighthouse customers for each of those verticals. That then become references to help you reach the rest of, the board in that domain and vertical. So repeatability is the name of the game for marketing rather than being extremely reactive to sales needs and these bespoke engagements that kind of become proof of concepts or little pilots rather than truly these wall to wall deployments. What you really need to do there is like. Cultivate. The other thing that marketing can be really good for is creating touch points or vehicles for the sales team to engage with these clients.

Krithika: So whether those are events or guides or reports that we're putting out, these are all reasons to reach out and knock on the doors of these prospects and potentially customers already in the pipeline. Enterprises are very slow to move. So whatever you can do to accelerate and catalyze that is going to be really important.

Krithika: So to me, those are some, definitely not all, but like some kind of thematic areas that marketing invests in to really kind of become and reach repeatability in the enterprise segment.

Brett: What about in the context of Retool, what are the marketing programs that you came up with that had sort of an outsized impact or maybe surprised you in some way in terms of how useful or impactful they ended up being?

Krithika: Oh, man, I, hinted at this before, but one of the biggest surprises for me at Retool was, how effective trade shows were for us. And so again, like coming back to that diagnostic, we had an awareness problem. People weren't aware of Retool as a tool that they could reach for a platform that they could reach for for building business software internally. So when we showed up to these trade shows where people were in the sort of mindset of curiosity and learning about new vendors or whatever it was, actually we did two things very differently at trade shows. One is we did not optimize for volume. Our sales reps were not, incentivized by the number of badges that they scan.

Krithika: Like we did not want low quality badges from these events. The second thing that we did was we did very custom demos for people at the event. And so we send very technical solutions engineers, product managers, sometimes engineers themselves, support specialists and developer experience folks. And they would do custom demos for people who walk by to say, Hey, you're in the healthcare space. you know, actually there was a great example at AWS ReInvent where someone walked by and they were coming in from a very big university and we showed them how they could build a tool to catalog all of the different faculty and the courses that they did and how can you sort of allocate the right scheduling for them and that happened right on the show floor and that led to a very strong sort of lead that went through towards the end of the quarter. and so that sort of personalization and customization, you think you can't scale that at a place like a trade show, but I think with the right sort of systems and support, you absolutely can sort of the right base templates. You can customize very quickly and show off the product very quickly, that I think paid off a lot of dividends.

Krithika: And then of course we tracked very meticulously how many deals were impacted or accelerated or catalyzed based on those and the very first trade show that we did was more than 3x ROI payback on the investment that we put into the booth. And so, We are very excited to do more of those, but I think my ethos here is like kind of try you experiment, you test, and then you invest further on the places that work.

Brett: One of the things that you sort of got out when you were talking about going after the enterprise in the context of Retool is verticalizing around use cases or sort of more problem and solution sort of selling. I'm interested in maybe what else you figured out in marketing horizontal pieces of infrastructure products relative to, you know, stripe in the early days.

Brett: You want to accept payments, is very clear problem, very clear solution. It's entirely different when you have a horizontal product, is the answer always trying to verticalize? Are there other things that you've kind of figured out around marketing horizontal products?

Krithika: Look, like I've only had the pleasure of working at platform companies in my career at this point. And I think each of these kind of falls into slightly different axes that you might cut on. When I think about something like Stripe, even though you think of it as simple as accepting payments, there are so many differences in terms of the business model.

Krithika: So, you know, you have SaaS companies that need subscription billing. You have e commerce companies that are doing sort of one time transactions. You have marketplaces like Uber or Airbnb that are not only accepting payments, but then paying out to the supply side of their marketplace. And so at Stripe, we actually started off with solutions that were based much more on your business model.

Krithika: And we would create these solutions for SaaS companies, for marketplaces, for e commerce companies that would collate together a bunch of capabilities across our platform and API. At OpenAI, for example, even though there are some horizontal use cases, so for example, you know, you might want to do something around semantics or, or you might want to do something around a better natural language processing or a better text to speech or translation type of use case.

Krithika: These feel fairly horizontal and, you know, a financial services company can just as easily avail of these three solutions that I just mentioned as someone in a manufacturing industry or so on. But what we found is that people tend to be much more following the leader in the space. And so they would rather do something that another fintech company or another healthcare company is doing, rather than thinking from first principles on, Oh, we have a customer support use case.

Krithika: So even though we're in healthcare and, you know, Karna. is in e commerce, the solution is the same. Like they don't think that way. So we have to get much more vertical based in terms of how we sell very horizontal solutions there. And Retool, again, it's a very broad platform. You can use it to build any sort of business software in the world.

Krithika: And so, it was a combination of the two. So we had to kind of do a combination of roll and vertical in order to make that really resonate. So if you were in, user operations or in marketing or in product management, you may have a different set of use cases that you're building for within your company.

Krithika: And then we had to combine that with case studies and logos for your particular vertical in order to have them really resonate.

Brett: So did you start to think about success in marketing in each one of those quadrants, as opposed to like, how are we doing in marketing globally?

Krithika: Yeah. So, at Retool, it was almost like a heat map of role X vertical, and then you kind of wanted to see how green could you get in maybe 10 of those :in a year. Like, I don't really think you could do much more than that. And so one of the first ones that we did was around software companies and how we were helping them get to market faster.

Krithika: Then there was something around customer support and how we were helping user operations move faster in the retail and manufacturing space. So yeah, it was very much a access and heat map situation. 

Brett: Maybe switching gears a little bit, you mentioned that kind of your most recent chapter is at OpenAI which is kind of its own interesting, fascinating journey. I'm sure just in the past year, has there anything that, that being involved in that company has. kind of influenced or changed your mind as it relates to marketing?

Krithika: Inbound demand that we see at OpenAI is unparalleled and we get to, in some ways, pick and choose the customers that we work with. And so many of the customers that we're working with are at the very forefront of AI, like they are pushing the horizons of what's possible even with our technology and the technology changes constantly and they are keeping pace or outpacing us in terms of the real world impactful use cases that they're building with us.

Krithika: But the thing that I'm even more convinced about is that every company that is trying to be effective of marketing has to have a really crisp point of view. They have to be extremely opinionated. And so at OpenAI, you know, the approach that we could have is saying, Hey, here's this whole box of Legos.

Krithika: You can build whatever you want with it. And we are very accommodating of whatever you want to create with the technology. That may be true, but what there's really appetite for in the market is for us to come in and say, Hey, if these four use cases are not part of your AI roadmap in the next 12 to 18 months,

Krithika: you're going to be behind your competitors, you're going to be behind the market. And this is how you should be thinking about the space. You shouldn't be thinking about AI as sort of a, a checkbox that you tick off in a quarter or two quarters. This is a new way of operating for the decades to come. And so that mindset shift, that mindset change is something that any company can do, but like you really had to be intentional about what is your perspective? What is your point of view? What is your opinion? If your friend who is a founder sat down with you at lunch and asked you for your true opinion on how they should be thinking about running their business or thinking about their roadmap, what advice would you give them?

Krithika: And why can't you do that at scale? Like that's the real question that I asked myself now at OpenAI because we do have this leadership position. But I think with that comes a lot of responsibility. Not just in terms of, you know, privacy and safety and how we approach the model development, but also how we approach our marketing and what we recommend our customers do.

Brett: Do you think marketing strategy needs to be different when you're the market leader versus the person that's trying to displace the market leader?

Krithika: I think it often is but I don't think it should be. There's an analogy that's often drawn to sailing and racing and sailing where the person in second position gets the same winds, gets the same weather, gets the same currents as the person in the lead.

Krithika: And all they have to do is, is follow and make sure they don't fall behind. And it's kind of unfortunate because I think actually like the people who are the underdogs have such a scrappy mentality and they take every opportunity. They kind of go 110 percent for every at bat that they get. And I think oftentimes in the market leadership position, you kind of can get into the sense of complacency.

Krithika: And I think, one of the operating values at Stripe when I was there was, and that's changed and evolved over time was we haven't won yet. And it was a mentality that was deeply ingrained into the DNA of the company. And it meant that even when we were in the leadership position, we never took that for granted.

Krithika: And I bring that to me anywhere I go. And so even with OpenAI, you know, you think it's our lead to lose. I mean, that's the better way to think about it instead of like, we are the market leaders, we have the market leadership to lose. And so I think, again, coming from that combination of that sense of responsibility to bring AI very responsibly into the world and second, like helping our customers navigate the sort of pathways ahead.

Krithika: I make sure that the team is taking 110 percent at every at bat that we get.

Brett: What's been interesting about having product that is both used by businesses and consumers in the realm of marketing?

Krithika: It's not a challenge that's shared by most companies. I'll, I'll tell you that. Having a killer consumer app and a platform play and businesses use our app too, right? So you have the B2C motion, you have the B2B motion that is more of a seat based SaaS license and then you have the B2D motion in terms of people using the API to build on top of.

Krithika: I think each of these have different measures of success and different programs that make them successful. And each of them kind of comes with its own diagnostic problem. So with the B2C space, for example, the insight that we get from talking to our customers and talking to just like the population at large,

Krithika: the people are aware of OpenAI. They're aware of chat GPT. We don't have an awareness problem, but what they don't often see is sort of the use cases or what they should be using it for. Or, you know, what could they be using it for? And so. creating that use case epiphany is the real challenge in the consumer space.

Krithika: We see a lot of companies kind of just falling back to, you know, you can generate crazy images of cats in space and they look very visually stunning, but they're not like durable use cases that are actually like impacting your day to day. And in Chat GPT, we see more than a hundred million active users on a weekly basis.

Krithika: We see a whole spectrum of uses, everything from improving your writing, to learning a new language, to planning the meals for your vegan teenager, to, doing some trip planning, like, honestly, it, it really spans the gamut. And I think the marketing challenge is really showcasing and storytelling some of these really impactful use cases.

Krithika: You know, we, we heard this great story of, a dad who was using chat GPT and especially the voice mode of chat GPT in order to help their um, severely autistic daughter engage better in school. We hear about people who have really created breakthroughs in their domain, just using chat GPT as a thought partner.

Krithika: Like, we want to be able to tell those stories so that when you have a task to be done, you think of using ChatGPT first. On the B2B space, it's a little bit more direct, right? Like we want to make sure that people can understand having a super assistant for everything that you do at work is important. I think the people at the ground level get it, but I think the people in the admin level think of it as yet another subscription that they have to pay for versus everything else that already has some kind of AI sticker on the box. And so it's really, the onus is on us to kind of help people understand why having a standalone workbench, it can become this like super assistant for your team. And the capabilities will continue to improve and grow and change over time, is an important investment today than ever before.

Krithika: And on the developer side, you know, there's a lot of options in the market. Um, I'll be the first to admit that developers have a plethora of choices in terms of the models that they use the infrastructure that they use and the tool chain that they use in order to build their software. So we have to invest in developer experience.

Krithika: We have to be the easiest and and most powerful way to build the applications that they want to build. So it's about winning the hearts and minds of developers, but doing that in an authentic way and earning the right to be the de facto for them.

Brett: How do you think about, and it may be an org design thing, or it may be an information flow sort of thing about like the common primitives in marketing that you want to have flow across all three of these constituents versus we're going to have a marketing team and they're kind of doing their own thing for this customer and they're thinking about their own world.

Brett: And then another marketing team that's thinking about sort of this other set of constituents, because there's obviously, as you articulated, there's a balance of, there are, I'm sure a lot of similarities in the way that you tell the story of the company and in certain degree the, the product but they're also very distinct, like, you know, trying to get a teenager to use ChatGPT is different than a fortune 1000 deciding what model they're going to build on top of. 

Krithika: No, absolutely right. I'd be lying if I say I've cracked it, but I think we have made some progress on two specific arenas that I think are really important here. Again, I worry about generalizing advice here because OpenAI is in a little bit of a unique position in the ecosystem, the products that we operate and the type of go to market that we have.

Krithika: And so, I hope some of these are applicable to other companies as well. The first arena is that you have to kind of rail against it. Like you have to rail against people getting too specialized into particular product areas because, okay, let's take for example, the global 2000, like the fortune 500 set, they just want to work with open AI. They don't really care whether it's chat GPT enterprise or, you know, this API or that API or whatever it is, they want to partner with open AI.

Krithika: And so, us showing up with an account director or a salesperson for the chat GPT product and a salesperson for the API product and them not being able to speak to any of the other products would be a huge miss. And so if we're just supposed to be the thought partner for them in navigating this AI landscape, we want to make sure that we're showing up that way.

Krithika: So even in terms of like rethinking org structure, rethinking the sales narrative that kind of spans, again, goes to the customer problems rather than our products first. Is something that's really important to us. So you kind of had to rail against it as a leadership team. The second is I think you want to kind of create the right set of centers of excellence, if you will. So whether that is, you know, the website team or, the brand marketing team that is thinking about campaigns or the competitive intelligence group that is thinking about how to feed in our competitive intel into the rest of the organization in a really productive and useful way.

Krithika: I think the one that you can't kind of, overly horizontalize is product marketing. They have to be very close to the products that they are working on, the feature sets that they support, but the rest of the teams could be fairly horizontal. And then it's really on you as a leader to help stack rank and prioritize the initiatives that matter.

Krithika: So. Is it really important that we read colleges and educational institutions, or is it really important that we're focused on the Fortune 500, or is the vegan teenager the most important segment of the consumer population, or is it a developer audience that is thinking about using Chat GPT for coding?

Krithika: So I think those trade offs can be made at the leadership level, but maybe some shared. infrastructure with these centers of excellence can kind of create ways to operationalize the campaigns, the launches, the initiatives that you want to put out into the world.

Brett: Maybe something you could talk about in terms of maybe how it manifests is I think in the past few months, you sort of relaunched the open AI site, and it feels like you took a departure from where you were. And obviously you do this stuff with a lot of intentionality. And again, you kind of have one common site that you have all these different types of people coming to for different types of things.

Brett: I mean, I'm sure you could spend hours talking about that project, but are there considerations or the way that you went about it that might be useful to other people that are, are taking on kind of a big meaty marketing kind of project like that.

Krithika: Ooh, yes. So many learnings. The first thing is, it was a departure from where we were previously because, for the vast majority of its history, OpenAI was primarily a research organization and all we were doing was communicating about research breakthroughs with the rest of the world. And now we operate products and services that a lot of companies, a lot of individuals rely on on a daily basis in terms of running production workflows and use cases, or relying it for on their jobs or for their daily lives.

Krithika: And so I think kind of moving a little bit of the balance, like we will always be a research organization. That is the DNA of the company. The mission of the company is deploying safe AGI. And so it's never going to become just a product company, but I think bringing in some DNA of product and that influence of ChatGPT into the rest of the presence on the web was important to us.

Krithika: A lot of people know OpenAI for ChatGPT. And so the fact that it wasn't up front and center, it wasn't easily findable was I think disingenuous. So that's why we now have ChatGPT kind of upfront and center on the website. The other part of that is the consistency piece that we talked about, Brett, which is, you know, you have one brand for ChatGPT.

Krithika: You have one brand for Open AI, another brand for the API. Like it's all kind of one in the same. It's the underlying models and you kind of use them and utilize them in different pathways and different product surfaces. So. We wanted to bring that ethos of that consistency across all of it too. Some of the learnings, I think one is, this never changes whether you're a small company or a big one, but you got to get people aligned.

Krithika: You have to make sure that people understand the goals, people understand the North Star, people understand the trade offs that you're making because you're never going to make any one constituency fully happy with a site like that. Uh, we considered a lot of different options. We workshopped and made sure that this was the best outcome for the, top five audiences that we most cared about.

Krithika: The other is like the trade off, right? Like there's a couple of different schools of thoughts when it comes to brand architecture. Some are companies that really care about one single brand. So for example, whether you're buying an iPhone or an iPad or a Mac Book, or just using a you know, the Photos App, for example, you still associated that with Apple.

Krithika: It's a branded house. Or on the other side, you have something like a Meta where you have Instagram and WhatsApp and Facebook and really your brand loyalty is with those, uh, sub brands and it's a house of brands. So is it a branded house or a house of brands? And I don't think you can kind of fall somewhere in between.

Krithika: You have to kind of pick one or the other. And for us at OpenAI, you know, again, the mission is AGI and we have different vehicles with which to push forward products experiences to help people get that, whether it's developers infusing that technology to their own products and experiences. Whether it's consumers using ChatGPT directly as an app, or any of the future products and experiences we may launch, we want that imbued with the same kind of underlying investments that we're making around privacy, safety, data security the sort of responsibility and approach that we take towards model development and AI development and the future AGI development.

Krithika: I think it's really important that, this becomes a branded house rather than a family of brands.

Brett: I'm really interested, someone were to watch you and your marketing team operate on a daily or weekly basis, how are you, leveraging the tools that OpenAI builds to do your own jobs.

Krithika: I can honestly say we probably use ChatGPT on an hourly basis. And so for everything that we do, everything from like strategy memo writing, to copywriting for external use cases, to even ideation and thinking through things, or synthesizing data, or you know, in, in my early weeks at OpenAI, we launched ChatGPT Enterprise for the first time and our lead volume went through the roof.

Krithika: And so I worked with Chat2BT to create a Python script that was our first lead scoring module that we put into production for the sales team. So we literally use it for everything and I've become quite dependent on it. Are we using it in the most innovative and novel ways? I probably wouldn't say so.

Krithika: Sometimes when I hear about our customers use cases or we write up a case study of a customer, I sometimes feel very envious and jealous of them because they've been able to implement AI in a way that is much more intentional and thoughtful and has become part of their automated workflows rather than just as a one time transactional assistant, if you will.

Krithika: And we're starting to get there, but in some ways, you know, we are keeping up with the market and we're moving at hyper, hyper growth velocity. And so sometimes it takes a little bit more of that intentionality to get right. So I'm, I'm committed to doing so, but again, I don't think we're at the forefront of how best to use AI as marketers, but we certainly are using it in a variety of different ways.

Brett: Why do you think that is? 

Krithika: Of not quite using it at the innovative way.

Brett: mean, it's quite counterintuitive.

Krithika: I think one of the reasons is, we're so focused on the foundational models and what they can do in their capabilities. and less so on the application of them, the tangible application of them. Like we're an AI company and so we actually really appreciate seeing from the crowd, like what they can use it for. Like, we don't always have all of the answers and we don't often launch with the intention of it can be used for this use case or that use case of that use case. Like, of course, we run evals. We know sort of generally where it's going to be the most applicable.

Krithika: But I don't think we go out with the intentionality of saying this is going to be really purpose built for this use case. I, we like seeing the generation of that in our ecosystem and then we apply and take on some of the best options ourselves.

Brett: Were there any marketing use cases where people were using ChatGPT or, your infrastructure that you were just. Kind of really taken by or thought was really brilliant.

Krithika: Yeah. Brett, one that was really interesting to me was um, Coca-Cola. They created a holiday campaign around Diwali and Christmas where people could kind of generate their own Coca-Cola poster with their branded assets, the polar bear and, and so on. And they did a fantastic job of it. And I thought from a campaign generation perspective, that was probably one of the most like innovative and novel ways that I had seen the API used.

Krithika: In terms of overall though, in my conversations with CMOs and marketing leaders, I feel like most people are kind of making a mistake. They kind of go out and deploy chat GPT into their workforce. But they expect it primarily used for writing like whether it's blog posts or marketing collateral or content, and they're not thinking about the systems that you need to integrate into, the workflows that you want to automate, the true like business processes that you want to put into AI and automation so that you could focus on more strategic levers, getting to know your customers better, getting deeper into the product space. So that for me is, is a miss. I think the other way that people aren't using AI is to say, uh, they think of it as like an augmenter for their existing workforce, but not in the way that I would predict, you know, for me, some of the most novel ways that chat GPT helps is it makes a fantastic brand marketer also really good at data analysis because it can help them run those regression analyses on the data or, you know, it takes someone who is extremely data driven, maybe they're in, in marketing ops or a data scientist and can help them come up with fantastic logo ideas or branding ideas or naming ideas. And I think that kind of cross pollination of the variety of different marketing disciplines.

Krithika: Could help you become much more well rounded as a marketing organization if you use it to bring superpowers that people don't already naturally possess to the fore.

Brett: So switching gears again, most of the conversation we've had, has been sort of through the eyes of the marketer. I'm interested in sort of shifting slightly and talking about sort of the founder role as they think about that first marketing hire. I'm sure because you've had this role multiple times.

Brett: Lots of founders are asking you, you know, when is the right time? What is the spike that I should be looking for? so I'm curious if I were to listen into sort of one of those founder conversations. Let's say there are 20 people or 30 people. They have a million in revenue, like there's something working, how should they think about who should be in that seat?

Krithika: The first question I always ask is, when you get into a conversation with a prospect, a potential customer how likely is it that you close them? And what that tells me is they have product market fit. It sounds like it from already the business dynamics, but the second is, do they have a pitch that is resonating?

Krithika: If you can get people into a room and close them well, what you need is more fire at the top of the funnel. Like you need a demand generation person who can bring in more awareness, more leads, more conversations into the funnel.

Krithika: If they're saying like, yeah, for the most part, like some people really get it, some people really don't, that probably means you need more product marketing help, like someone to kind of come in and help articulate that differentiation and positioning in a way that gets you much more likely to win those deals, whether it's writing up ROI through case studies, or whether it's like creating more compelling narratives for the pitch, creating solutions and starting to think through use cases in much deeper ways.

Krithika: So that to me usually drives who your first marketing hire is, like whether they spike much more in demand gen or much more in the product side, but it's usually one of those two when you're first starting out.

 What do you look for in the first hire? Meaning if you think about a demand gen leader, that would be the right 20th person on a marketing team at scale versus somebody that has that ability, but is the right person to join as the first marketer. Do you think about what a founder should be looking for or a hiring manager differently in those two situations?

 Actually it's really hard to give like one answer to this, but I would say a few facets that I would look for, is this person kind of coming in with a playbook? Like, do they have a set of things that they usually do at a company that they feel very comfortable doing and they would just sort of suggest you do that because at the stage of your company or whatever else, or can they get really personalized and customized for the needs of your company? And so I would usually start by doing a pretty deep workshop. Like I am not a very big believer in take home exercises, especially for very senior roles, but if you can do a workshop and get in together and start whiteboarding, what is this person saying? Like, do they understand the dynamic of this particular company? What you're trying to do differently, what you're trying to disrupt and creating marketing strategies alongside that compliment that?

Krithika: Or are they saying, Hey, for your stage of company, you know, you, we should be investing in. paid marketing and starting to do events and starting to do content. Like you don't want the playbook, you want something that is very unique in the same way that your company is unique. So someone who can get very customized is one facet that I would look for.

Krithika: The second is like intellectual curiosity, like someone who has played with your product, gone through the onboarding flow, can kind of start to understand the dynamics of who your customers are. So are they going and doing that homework or are they expecting you to pitch them? At some point in the recruiting conversation, it has to flip to the other side where they're showing that curiosity and excitement about the product.

Krithika: I'm personally a marketer who cannot market a product I don't believe in or haven't used myself. And so, I think you want someone who can get really excited and with that same enthusiasm, go and pitch your product and get excited about sharing it with the world.

Brett: You sort of hinted at this was sort of workshopping, but what advice would you give in terms of what is a good interview process look like for that first marketer?

Krithika: For the first marketer, you are going to be spending time with them in the same way that you would for any leadership hire. So if you're spending a day with your engineering manager or you're having them spend time with the rest of the engineering team, if you're thinking about product roadmap together, you kind of want to do something similar for your marketer.

Krithika: The marketer is a very hub role that ends up having to interface with the product team, with the engineering team, with the, , design team, with the leadership team, with the rest of the organization, maybe even recruiting, right? Because you want to build a talent brand. And so you want them to get along well and be someone who can be a thought partner and someone who pushes the thinking of the rest of your leadership slate as well.

Krithika: So I would invest quite a bit in this one so that you understand how are they going to change the dynamic? How are they going to improve the dynamic? One question I always ask yourself is, did I learn something from that conversation? Did I learn something that is going to change my thinking about something that I'm already trying to move ahead in my company?

Krithika: And I think that's a mark of a great marketer.

Brett: As you're starting to scale a company as a founder, one of the more interesting topics is How do you hire for something you really know nothing about. In a lot of cases, I think the first marketer is an example of an area that, that a founder does not have deep expertise versus something like a VP of engineering, a first PM, et cetera,. Is there anything else that would increase the hiring accuracy for the founder in this area? You know, assuming the founder is not a marketer.

Krithika: Two things that feel counterintuitive, like don't always go by the brand pedigree of the companies that people have worked at, like get really deep with what are the initiatives that they really moved ahead? What are the work streams that they came up with the idea about and then went and executed?

Krithika: What are some of the failure modes that they faced? What are some of the biggest challenges that they left kind of undone at their previous company? So sometimes, you know, high growth covers all wounds. And so did this person actually make an impact or was like the rising tide, , something that lifted them as well?

Krithika: The second thing that I would say is like, don't set these dumb exercises that many founders do, which is just like, write me up a 30, 60, 90 days strategy plan, like, Anyone with access to Google can come up with a fairly good document on that front. You want someone who can get very deep on your funnel and speaking of funnels, I think finding someone who has worked at companies that has a very similar dynamic as your company, whether it's PLG or self serve or developer led or enterprise , tops down, it is much easier for someone to switch domains that they work in, but it's very hard to switch the type of funnel that you've operated.

Krithika: Because if you're doing enterprise tops down sales, the type of channels and programs and initiatives and the type of materials that you might have to create to reach that audience is very, very different than if you're doing self serve work where you have to create scaled content, whether it's videos, recordings, written documentation, guides, infographics Versus if it's PLG, that sort of handoff and creating the mechanism, figuring out the lead scoring, figuring out the product lead scoring.

Krithika: Those things kind of come with experience and they come with a repetitive exposure to that kind of funnel. And so if you're willing to take a bet on someone who has worked on a very different funnel mechanic. Just know that it's going to take them some time to ramp versus being able to look around corners.

. Well, maybe where we could end is sort of one of my favorite questions, which is, in, in the context of marketing who has taught you the most in your career? Is there a single person that kind of imparted something or shaped the way that you think about marketing in a disproportionate way?

Krithika: It's a really hard question to answer because I think it's been more of a Captain Planet sort of situation. A little bit of this from this person, a little bit of that from that person. A few shout outs that I'll give. One was my first manager in marketing. Kenzo Fong at Android and Google.

Krithika: And he really taught me a lot about the impact that brand and the investment in brand marketing the outsized impact that it can have on new products that you bring to the market. Tanya Khakbaz at Stripe was my manager. And she really taught me a lot directly in terms of how to up level product marketing, but also taught me through osmosis and gave me permission in terms of how I could show up in forums and how I could engage with some of my cross functional partners. And then in terms of brand and developer marketing I learned a lot from Greg Brockman, both at Stripe and now at OpenAI in terms of how to reach developers very authentically, how to remove and strip the marketing of, all the marketinginess and the fluff in order to be very authentic to the developer audience.

Krithika: So, more of a captain planet system here.

Brett: Cool. Great place to end. Thank you so much for spending the time.

Krithika: Great to meet you. And thank you for having me.