Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman

Krithika Shankarraman was the first marketing hire at OpenAI and Stripe and led marketing at Retool. At OpenAI, she established marketing foundations for ChatGPT for consumers and enterprises, as well as their developer API platform. While at Stripe, she spent over eight years building and scaling their marketing function from scratch. An engineer turned marketer, Krithika brings a uniquely analytical approach to marketing. She currently serves as Entrepreneur in Residence at Thrive Capital, where she helps portfolio companies on all things marketing. *What you will learn:* 1. Why do most marketing playbooks often fail, and what’s a better way? 2. Which marketing lever should I pull first? 3. Why is trying to be better than competitors usually a losing strategy? 4. How do I craft positioning that actually converts? 5. What makes messaging stick with developers, enterprises, and consumers? 6. What pricing experiments actually move revenue? 7. What is working at OpenAI really like? 8. Why does consistency and quality matter more than speed? *Transcript:* https://www.lennysnewsletter.com/p/growth-tactics-from-openai-and-stripes-first-marketer *Brought to you by:* • Eppo—Run reliable, impactful experiments: https://www.geteppo.com/ • Airtable ProductCentral—Launch to new heights with a unified system for product development: https://www.airtable.com/lenny • LinkedIn Ads—Reach professionals and drive results for your business: https://www.linkedin.com/podlenny *Where to find Krithika Shankarraman:* • X: https://x.com/krithix • LinkedIn: https://www.linkedin.com/in/krithix/ • Website: https://krithix.com/ *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction to Krithika (04:22) Early marketing lessons from OpenAI (11:17) Diagnosing marketing needs (15:06) The DATE framework and why being cheaper is a race to the bottom (17:11) Marketing strategies at Retool (22:29) Insights from marketing at Stripe (32:33) The importance of consistent marketing communication (39:55) Criteria for hiring a marketing expert (41:43) “Capital M” vs. “lowercase m” marketing (43:05) ChatGPT vs. Claude: market dominance (45:31) The future of AI and its societal impact (47:09) Work-life balance (48:41) Transitioning to Thrive (52:35) Career advice for marketers (55:00) The importance of taste and creativity in the AI era (01:00:04) AI product pricing (01:03:21) AI tools in marketing (01:05:17) Failure corner (01:08:46) Lightning round and final thoughts *Referenced:* • OpenAI: https://openai.com/ • Stripe: https://stripe.com/ • Retool: https://retool.com/ • Dropbox: https://www.dropbox.com/ • Sam Altman talks about his business model: https://www.youtube.com/watch?v=pLnyjxgFxew • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan • Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy • Netflix: https://www.netflix.com/ • Stripe Connect: https://stripe.com/connect • John Collison on X: https://x.com/collision • Patrick Collison on X: https://x.com/patrickc • Cristina Cordova on LinkedIn: https://www.linkedin.com/in/cristinajcordova/ • Hackpad: https://en.wikipedia.org/wiki/Hackpad • Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy): https://www.lennysnewsletter.com/p/building-wiz-raaz-herzberg • Wiz: https://www.wiz.io/ • Thrive Capital: https://thrivecap.com/ • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Claude: https://claude.ai/new • ChatGPT: https://chatgpt.com/ • Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics • Databricks: https://www.databricks.com/ • Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch ... References continued at: https://www.lennysnewsletter.com/p/growth-tactics-from-openai-and-stripes-first-marketer *Recommended books:* • Obviously Awesome: How to Nail Product Positioning So Customers Get It, Buy It, Love It: https://www.amazon.com/Obviously-Awesome-Product-Positioning-Customers/dp/1999023005 • Circe: https://www.amazon.com/Circe-Madeline-Miller/dp/0316556327/ _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email [email protected]._ Lenny may be an investor in the companies discussed.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  It seems like there's a playbook for everything. There's a framework for everything. But the reality is you have to spend the hours and the time to really understand your customer.

• 0:08Lenny Rachitsky?

  You were the first marketing hire at OpenAI. I believe ChatGPT is the fastest growing product in history. Let me ask you this, a lot of people might be hearing like, oh, ChatGPT. It's like, why do you need marketing?

• 0:18Speaker 00

  Everyone knew of ChatGPT. But when you clicked one zoom level further, the thing that came up was, I don't know what to use it for. The work of marketing ended up becoming, creating this sort of use case epiphany where people could say, I had no idea ChatGPT could do that. A lot of marketing metrics tend to be vanity metrics about the number of clicks that you got, number of views, number of impressions. I think those are all bullshit numbers. What is that experience that you want your customers to come away with when they interact with your brand?

• 0:45Lenny Rachitsky?

  If your advice is don't just copy what other companies do, what should people be doing?

• 0:49Speaker 00

  Put together like a four step process that has served me pretty well. The first step here is.

• 0:55Lenny Rachitsky?

  Today, my guest is Krithika Shankar Ramen. Krithika was the first marketing hire and VP of Marketing at OpenAI, the first marketing hire at Stripe, where she was the only marketing person for three years. She was also an early marketing leader at Retool and at Dropbox. She also did marketing for Android at Google. Currently, she is Executive In-Residence at Thrive Capital, where she supports their portfolio and founders on all things marketing and helps hire early marketing leaders for their startups. In our conversation, we talked through all of the biggest lessons that she has learned about how to market your product from her time at OpenAI, Stripe, Retool, Dropbox and other places, including her four-step diagnostic approach to marketing, her anti-playbook playbook, what B2B companies can learn from consumer marketing,

• 1:39Lenny Rachitsky?

  career advice for people looking to get into marketing, and also just what people that don't want to get into marketing should know about marketing to be successful. A big thank you to Kevin Garcia and Kelly Sims for suggesting questions and stories to get into. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you get a year free of a bunch of world-class products, including Superhuman, Notion, Linear, Perplexity and Granola and more. Check it out at lennysnewsletter.com and click Bundle. With that, I bring you Kritika Shankar Ramen. This episode is brought to you by Eppo. Eppo is a next-generation A/B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams.

• 2:23Lenny Rachitsky?

  Companies like Twitch, Miro, ClickUp, and DraftKings rely on Eppo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features. And Eppo helps you increase experimentation velocity while unlocking rigorous, deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform, where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Eppo does all that and more with advanced statistical methods that can help you shave weeks off experiment time, and accessible UI for diving deeper into performance, and out-of-the-box reporting that helps you avoid annoying, prolonged analytics cycles.

• 3:06Lenny Rachitsky?

  Eppo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A/B testing flywheel. Eppo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Eppo at geteppo.com/leni and 10x your experiment velocity. That's geteppo.com/leni. This episode is brought to you by Airtable Product Central, the unified system that brings your entire product org together in one place. No more scattered tools, no more misaligned teams. If you're like most product leaders, you're tired of constant context switching between tools. That's why Airtable built Product Central

• 3:49Lenny Rachitsky?

  after decades of working with world-class product companies. Think of it as mission control for your entire product organization. Unlike rigid point solutions, Product Central powers everything, from resourcing, to voice of customer, to roadmapping, to launch execution. And because it's built on Airtable's no-code platform, you can customize every workflow to match exactly how your team works. No limitations, no compromises. Ready to see it in action? Head to airtable.com/leni to book a demo. That's airtable.com/leni.

• 4:25Lenny Rachitsky?

  Krithika, thank you so much for being here and welcome to the podcast.

• 4:29Speaker 00

  Thank you so much for having me. I'm excited to be chatting.

• 4:31Lenny Rachitsky?

  So you were an early and the first marketing hire at some of the most iconic companies in the world. What I want to do with our chat today is basically go through a lot of these companies that you've worked at and see what lessons we can extract about your time leading marketing at these companies. And I want to start with OpenAI, no big deal. You were the first marketing hire at OpenAI. Things seem to have gone really well over there. I believe ChatGPT is the fastest growing product in history. Does that resonate?

• 5:03Speaker 00

  It does. Not that I can take credit for it.

• 5:05Lenny Rachitsky?

  Well, we'll talk about that. Either way, nice job. Let me ask you this. A lot of people might be hearing like, oh, ChatGPT. It's like, like, why do you need marketing? It's like the most magical thing in the history of the world. Like, how much value does anything add to making it as successful? Can you just talk about just like the value that a marketing person adds to a product like that? That's already incredible.

• 5:25Speaker 00

  Yeah, when you think about all of the different stages of the funnel, awareness was clearly not the problem that ChatGPT or OpenAI had. Everyone knew of ChatGPT. But when you clicked one zoom level further, the thing that came up was, I don't know what to use it for. Like, I don't know what it replaces. Like, should I be using search for this? Should I be using ChatGPT for this? Or how can it even help me? And so the work of marketing ended up becoming, creating this sort of use case epiphany, where people could say, I had no idea ChatGPT could do that. And yeah, maybe I should be using it for XYZ reason in my own life. And so I think you had to be very diagnostic in terms of what can marketing be doing to help, rather than just going off of the typical top of funnel and then middle of funnel

• 6:10Speaker 00

  and conversion oriented tactics that end up being in playbook.

• 6:14Lenny Rachitsky?

  So for folks that listen to this podcast, it's a lot of product managers, product builders. They don't, a lot of them don't have a lot of experience with marketing. I think it's an important insight there of just like, this is a thing marketing can help you with, is helping people understand how to use your product, understand use cases, understand examples, things like that. So I think as we go through this, I think this is useful for folks to understand of like, here's what you may not be good at and may need marketing help with.

• 6:38Speaker 00

  You know, when done right, product management and product marketing should be best friends, right? And you're working together at every stage of product development, rather than thinking of it as a handoff at the end of the conveyor belt when the product's been built, you sort of hand it off to marketing to take it out the door. If you can think of it as sort of a three-legged race from the very beginning of product development, then you go to market with the right thing in the first place. You get these insights from customers. You hear the language that they're using, which can be the sort of cheat code for how to message and position the product in market. And of course, there's like a creativity angle on how to differentiate your product in the market, but ideally, you're doing that in lockstep with the product management side.

• 7:18Lenny Rachitsky?

  The other element of ChatGPT's marketing success, I know that you spent a lot of time on the enterprise side, is just like consumer-ish marketing tactics for enterprisey products. Can you just talk about that? And it feels like that's emerging more and more, just like consumer tactics for enterprise products.

• 7:35Speaker 00

  In typical organizations that I've been a part of and leading marketing for, the enterprise side of the house, the B2B side of the house, usually fits the mold of demand generation, where you're creating demand for the sales team, and you're bringing new customers and prospects into the fold and into the orbit of the company. That, again, was not the problem at OpenAI. When we turned on the contact sales form for ChatGPT Enterprise, which was one of my first launches at the company, our lead volume 40xed overnight. It was unanticipated, even beyond our wildest expectations. And so, some of the things that I had to do are not typical to marketing at all. Like, I sat down with ChatGPT and I coded up a Python script that ended up functioning as our first lead qualification,

• 8:19Speaker 00

  lead scoring model, that was used in production for way too long, longer than I'd care to admit.

• 8:25Lenny Rachitsky?

  It's so funny. I think about when ChatGPT first launched and OpenAI just launched, everyone was just like, how will you make money? How do you make money with something like this chatbot? That's pretty interesting, like, smart, but sort of not that smart. I remember there's a video of Sam Altman being asked, how do you make money with something like this? And he's, I don't know if you just saw this, he just like, at some point, we will ask ChatGPT, how do we make money?

• 8:47Speaker 00

  And I think the reality is it's not a solved problem and a lot of folks, a lot of companies in the AI domain are trying to figure out the right pricing model. And it's something that you've talked about in your newsletter and so on, but there is a value creation aspect to using AI that doesn't neatly fit the mold of SaaS-based pricing or seat-based pricing or even usage-based pricing. So I think there are still some frontiers to figuring out where is the value? How do different types of organizations and companies and consumers find value? And again, it's not the typical sort of KPIs that you would typically try to optimize and maximize.

• 9:27Lenny Rachitsky?

  I will say though, in terms of pricing, it feels like chat GPT, it's like, it works. It's just like a monthly fee chalked to it up to a certain limit. It's wild to think back now, there was a sense, we don't have no idea how this make money. Like now it seems so obvious.

• 9:41Speaker 00

  Truly was a research preview.

• 9:43Lenny Rachitsky?

  And then I just, and I remember Sam only just launched here, check out this chat thing that we are trying with. And then it just, the fastest product growth in history, no big deal. I want to come back to this point you made about this playbook, anti-playbook kind of a thinking. You've kind of pointed out that with chat GPT and OpenAI, there was, there was no playbook. And you find that often people following playbooks don't work. Talk about that insight.

• 10:07Speaker 00

  In my current role and in my career, I've spoken with a lot of founders and typically the founders reach out because I've worked at companies that they look up to. And they're looking for that playbook. They're looking for, hey, just like, tell me how Stripe did it, tell me how Retool did it, tell me how OpenAI did it. And I really hesitate to share any such detail because there is a combination of context, competitive landscape, and the overall sort of zeitgeist of when the company is operating, how the company is operating, that really adds a lot of nuance to what works in the market. And so doing the same things, like if you're just kind of copying the outcomes or the outputs of the strategy

• 10:49Speaker 00

  and trying to follow in the footsteps of the tactics, you're not paying enough attention to the inputs and sort of, what were the variables and the deciding factors which led to that strategy in the first place? So what I like to do is try to unpack more of a framework for how do you get to become more of a diagnostician to understand the right strategy or tactic in the first place, rather than saying, how do you copy something that led someone else to success? Because Those criteria may not apply to you at all.

• 11:17Lenny Rachitsky?

  So let's follow that thread because everyone's like, goddamn, I need a play. Just tell me how to do this. Okay, so if there's no playbooks that you like, if your advices don't just copy what other companies do that have done well, what should people be doing? How do they approach figuring out how to market their product and help it grow faster?

• 11:35Speaker 00

  And so I was an engineer before I became a marketer. And so I have brought a little bit of an engineer's framework to the marketing side of the house. And so something that I've tried to do is put together like a four step process that has served me pretty well. The first step here is diagnosing, so diagnosing the actual problem. Again, this usually means taking a zoom back when a founder comes and asks like, hey, we really need to hire a demand gen leader. Like, who do you know in your network that we should be thinking about? And I'm like, let's talk about your funnel. Do you have a lot of people coming in at the top of the funnel? And when they do come in at the top of the funnel and you start talking to them and having a sales conversation, how likely is it that you close them? How likely is it that you win that deal?

• 12:19Speaker 00

  That usually tells you very astutely, do you have product market fit? Like, once you're already in the room and people are converting, you have found that problem statement that is critical to them, that is hurting them the most. And your solution is resonating as a as a solve to that problem. And so that means, yes, probably throwing in more at the top of the funnel is a very good move to make at that time. But on the other hand, if you say, yeah, I mean, like, we get a lot of interest, but once they're in the room, they have a bunch of questions. They're asking about, you know, how do you compare to X competitor and Y competitor? And why does it cost so much? And et cetera, et cetera. That probably means that there's more to be done in the product market fit zone rather than

• 13:04Speaker 00

  throwing in more at the top of the funnel because you have a leaky funnel at the bottom. And so hiring a demand generator, maybe the worst thing that you can do versus thinking about more of a product marketer who's thinking about the competitive differentiation, the positioning, the sales enablement that gets more people through at the bottom. So that's that diagnostic step at the top. Second to me is like analyzing your competitors' approaches. So to me, this is not about like being super laser focused on your competition because that leads to these local maxima rather than thinking about phase shift changes and breakthroughs that you can make as a company. But when you analyze your competitors' approaches, evaluating what others do in the space can kind of give you a useful baseline and identify opportunities and gaps and niches

• 13:48Speaker 00

  that your company can take in instead. And then this is the critical step. The next one is you have to intentionally take a different path than what everyone else is doing. And so driving a strategy that sort of sets the company apart is really critically important. I think it's so core to the discipline of marketing, ensuring that differentiation in the market. And you don't have to go into a cave to come up with these ideas and strategies. You can usually go and look at domains that are far outside of your own, rather than your direct competitors, and come up with some great ideas that you can cross apply and bring in and steal into your own domain or vertical instead. And then the final piece is just experiment, test, validate, all of that, and then scale

• 14:33Speaker 00

  what works and kind of discard what doesn't. So you really have to have a lot of that ability to throw away work when you might have spent a ton of calories on this wonderful piece of content, but if it's not working, don't double down on it. Like that bias of sunk, the sunk cost fallacy really comes into play, especially when you've poured your heart and soul into creating artifacts for marketing. So experiment, test, validate, give people that psychological safety to fail, especially your teams and organizations. And then, yeah, once you find what works, really double down on it.

• 15:06Lenny Rachitsky?

  Let me summarize what you just shared here. So essentially, if you think you're like, I need help with marketing, or I have a problem, and I think I'm gonna, I need to hire a demand gen person, or a paid growth person, or a SEO person, or, I don't know, content writer, or something like that, before you do that, first of all, go through these four steps. So step one is diagnose, spend time understanding what's the specific problem you want to solve. Then analyze, this is, this is so interesting, I've never heard it this way. So then it's analyze what your competition is doing so that you can then, one, find like inspiration and see where gaps exist. And then, sounds like the core part of it is just make sure you differentiate and choose a different path versus just try to be the better thing or the cheaper thing.

• 15:48Lenny Rachitsky?

  And then the final piece is just like, okay, here's our path. Let's test, run some small scale tests.

• 15:53Speaker 00

  Experiment, yeah. I'm a marketer through and through now. So I mean, you got diagnosed D, analyze A, take a different path T, and experiment for the E. So it's the, the date framework I just coined it.

• 16:06Lenny Rachitsky?

  Beautiful. Okay. We got a new framework. Cut off the presses. I love it. Date. Okay. So with differentiation, what's your thoughts on being, saying you're just a lot better or a lot cheaper?

• 16:18Speaker 00

  Being cheaper is a race to the bottom, especially when you think about sort of scaling laws and how things are playing out. Every company is sort of becoming an AI company at this time. And so as models get cheaper, more capable, being cheaper is not going to be the thing that really is a durable approach in the market. And I think in terms of doing things differently, it's not just for the sake of it. I think it's, it's really that novelty and that differentiation is something that people are craving for. They're not looking for yet another tool in the market. They are looking for something that aligns with their values, aligns with what their goals are. And so if you can be really crisp on understanding the user need, understanding what is the problem

• 17:00Speaker 00

  space in which they're operating, I think that kind of one-two punch of a fantastic product experience, and then the marketing experience to match can be a superpower for your company.

• 17:11Lenny Rachitsky?

  Awesome. Okay. So let's, let's go through an example of, of a company you did this with, and this may take us to another company you worked at, and the story's there.

• 17:18Speaker 00

  Yeah, one that comes to mind is definitely Retool. Retool was very different from both my experiences at Stripe and at OpenAI, because both Stripe and OpenAI, for better or for worse, were inbound companies, right? There was so much latent demand that we were fighting off people breaking down the door, trying to get to our products. With Retool, marketing was between the company and revenue, and we had fantastic product market fit with the enterprise space, with the developer community, but Awareness was a challenge. And so how do we go out, not just like wait inside of our house, waiting for people to knock down the door, but rather step outside of our house and start introducing ourselves to the neighborhood. So thinking about outbound channels and building

• 17:59Speaker 00

  demand engines was the name of the game. And here, you know, one of the ways to think about that is, hey, should we just scale the paid marketing channels that we already have working for us? And that's when the diagnostic really came into play, which is, what are the leads that are coming through the funnel? Are they turning into sales qualified opportunities? What kind of pipeline are they driving? A lot of marketing metrics, again, tend to be vanity metrics. They tend to be about the number of clicks that you got, number of views that a tweet got, number of impressions. I think those are all bullshit numbers. Like, really, what you want to be looking at is your impact on either signups, if you're a self-serve product,

• 18:41Speaker 00

  PLG, or in terms of a B2B company, sales leads and revenue that you're driving, pipeline and opportunity that you're driving. So we diagnosed that. And we found that for the most part, our paid social channels were doing not much for us. And so we had to invest in new engines. So that was that diagnostic. When we looked at some of the competitors, you know, we saw that they were doing a lot of content marketing, they were doing a lot of events programming, and like, we could have kind of followed in those footsteps, but there was the ability to take a different path. And so what we decided to do was double down on customer marketing and customer storytelling, because the thing that differentiated Retool from a lot of the copycat competitors in the market, was that we had terrific traction with true

• 19:26Speaker 00

  enterprises who were paying for the product, who believed in the product, who were expanding within the product. And so having them tell the stories on our behalf was so much more compelling. And no other company could replicate the kind of customers that Retool had in its bench. So we wanted to make sure that we were using those logos, we were using those companies to the best impact possible. And then we experimented. We tried to put together webinars, different types of sales dinners, different type of event formats, to see what actually worked best for us, and scaled the ones that worked and discarded the ones that didn't.

• 20:02Lenny Rachitsky?

  Okay, there's so much here. So in the diagnose step, I think a kind of a between-the-lines piece of advice here is look at what's already working. So you looked at, okay, we maybe paid growth, maybe this, maybe that. And then it's like, okay, what seems to be working is people find us through maybe another logo, another customer that's fancy and they're like, oh, Netflix is using retool. Oh, maybe I should check it out. So I think that's a really important lesson there is don't try to like, hey, we need to start expanding our top of funnel to all these different channels.

• 20:32Speaker 00

  And really litigate some of those channels too, because on the surface, they might be working, but are they actually driving pipeline and revenue?

• 20:38Lenny Rachitsky?

  Got it. So they may be showing like vanity metrics, top like numbers are nice at the top, but they're not sales qualified potential. They don't actually stick around. Okay. And then the analyze competition is really interesting. So again, it's just like, what are they doing? What, what can we be doing differently? Does it ever make sense just to do what they're doing, but do it better? Or is that like rarely a successful path?

• 20:58Speaker 00

  You still have to do something a little bit different. I recall a very specific example at Stripe, where, you know, our, our product Stripe Connect, which was made from marketplaces like Uber and Airbnb, where not only are you accepting money as a platform, you're also paying out people on the seller's side of the marketplace. And we were really, the, the competition truly was to become a payment facilitator. So rather than using another off the shelf service, instead of using Stripe Connect, you might go off and become a PFAK yourself. And a lot of the services organizations, the consulting groups that were helping companies become PFAKs, the things that they were doing was really leaning into that old school terminology, the jargon of the legacy systems and so on and so forth.

• 21:43Speaker 00

  And Stripe kind of figured out, hey, we need to rank higher for the SEO terms that people are searching for. So how do we help rank for PFAK without actually like talking about ourselves as a PFAK solution? So we decided to kind of do a reverse RFP system where we created a piece of content that said, hey, if you want to be a payment facilitator, here's the secret playbook. Like here's all the things that you have to do. And by the way, if this feels onerous or annoying, it is, and you should use Stripe Connect instead. So we're still a little bit of a zigging where others were zagging. Yeah. But I think if we had done the same thing in terms of becoming a consulting service to become a payment facilitator. Connect would be nowhere near the sort of run rate or revenue that it drives for the company.

• 22:28Lenny Rachitsky?

  Okay, this is a great segue to Stripe, which another company you were the very first marketing hire at. You were also, I believe, the only marketing person for three years at Stripe.

• 22:38Speaker 00

  I do not recommend that to anybody.

• 22:41Lenny Rachitsky?

  There's a lesson there. Okay, so let's talk about Stripe. What are some of the biggest things you learned marketing at Stripe that you think might be helpful to other marketing people and founders?

• 22:51Speaker 00

  Oh, man, there are so many things to choose from because I was Stripe for almost eight and a half years. Joining as the company's first marketing hire, you know, building that marketing function from the ground up. It really gave me the privilege of working very closely with our founders, John and Patrick. And John and Patrick, I would say, actually, I was not the first marketer at Stripe. John and Patrick were the first marketers at Stripe because they were developers themselves. They truly understood the developer community. And when that audience for Stripe was squarely developers to begin with, they knew exactly how to authentically reach that audience. And so I had to unlearn a lot of the things that I had learned at Google and Dropbox coming into Stripe in order to reach developers authentically.

• 23:33Speaker 00

  The experience really taught me the importance of deep product understanding as well. Like you couldn't really play act at understanding the product, especially when developers are trained to spot bugs, right? So not only do they spot those bugs in code, they spot those bugs in marketing and in blog posts. And so if the marketing pieces are your first impression of the product, they are an extension of the product itself. You have to hold yourself to a very high bar in terms of how you communicate about the product. And so we did a lot of investment in design work, in polish, in terms of how the marketing came together. And the value of creating marketing artifacts that were deeply integrated with the company's mission and the

• 24:17Speaker 00

  Craftsmanship that went into the product was another lesson that I learned very deeply at Stripe.

• 24:22Lenny Rachitsky?

  So kind of along those lines, again, people may look at Stripe and be like, okay, it's like the best thing ever for payments. Why do we need marketing? It's just like engineers build it and integrate its works. What is it that marketing most adds to a product like Stripe?

• 24:40Speaker 00

  Across my time at Stripe, marketing's are very different purposes. And so I kind of see it in different epochs or chapters as my time at the company. The first chapter, when I joined, our head of partnerships at the time, Christina Cordova, handed me

• 24:56Speaker 00

  a hackpad at the time, which is like a Notion doc.

• 24:59Lenny Rachitsky?

  I remember a hackpad that turned into Dropbox Paper.

• 25:01Speaker 00

  That's right. And so she had kept a hackpad, a secret hackpad away from the engineering team, which was all of the features and products that we had shipped, but had never communicated to our customers about. And so the launch sort of ended with shipping the feature rather than communicating with the user. So the first chapter at Stripe was really just getting through that backlog and making sure that the ethos at the company changed to say, hey, your launch isn't complete until, if you're just code complete, you have to actually ship it to the customer and make them aware of it. So usage became the North Star, engagement became the North Star, rather than just the binary, has it launched or not? The second chapter at Stripe was really starting to expand what a launch meant, right?

• 25:45Speaker 00

  So going from just putting out a blog post for people who were already subscribed to the RSS feed of the company versus thinking through, hey, how do we reach out to them through an email, through other channels? How do we really invest in this fanatical community that is getting so excited about the product experience? So we pulled together developer experience as a function, built out developer relations to really have that community feeling and vibe. And then it was about starting to think through the multi-product ecosystem. So Stripe went from a single-threaded payments processing company to one that had multiple different products and features for the audience and the user base.

• 26:28Speaker 00

  So then the work of marketing became, how do you help people understand and navigate? Potentially this multi-product ecosystem and platform to figure out what's the right set of features and solutions that they should be using for their needs.

• 26:41Lenny Rachitsky?

  And so this is again, a good example of marketing can do a lot of different things and depends on the stage, depends on the needs. It almost starts again with diagnose. Where do we need, where do we have a need for marketing and growth?

• 26:52Speaker 00

  And especially in hyper growth companies, I think you have to run that diagnostic every three months, every six months in order to stay adaptable and flexible because those top level goals do change. You know, at some point, we really had to figure out how to scale our sales function. We had to figure out how to scale internationally. And so being adaptable to that meant constant reprioritization and making sure that you were also hiring people who weren't super deep in particular disciplines, but having a team structure that was T shape, people who could be flexible to those needs of the company.

• 27:24Lenny Rachitsky?

  Coming back to your point about how there's no playbooks, is that, is Stripe another example where it's like, this has never been done before. We have, we shouldn't copy what other payments companies have done in the past?

• 27:34Speaker 00

  Yeah, if we did, we would still be talking about PCI compliance and payment gateways.

• 27:38Lenny Rachitsky?

  Hmm. There's so much of what you share that reminds me of Roz from Wiz, who also, you were an engineer originally. She was a product person. Yeah, I think, I don't know if she was an engineer, but a product person. So it's

• 27:51Speaker 00

  Their first PM, actually. Yeah, Roz is great.

• 27:54Lenny Rachitsky?

  Okay. And it's, I think there's a few things that are so interesting here. One is you both have like non-marketing backgrounds, like you went from another function. And I think you tell me, it gives you like a whole new perspective on marketing, not just like the traditional education of marketing. Is there, is there anything there?

• 28:09Speaker 00

  One thing that's definitely made me is very skeptical of most marketing channels and strategies and tactics. And so I would be one of the first people to say, like, is that really going to work? Like, what developer is clicking on paid ads? Isn't a better thing that we could be doing for them, telling them to install AdBlock? And so So I think that skepticism means that you just have a higher bar for the quality of the content, the substance of the content. You want to make sure that the marketing is as substantive and as crafted as the product experience itself.

• 28:40Lenny Rachitsky?

  The other really interesting corollary here is she was very big on like avoiding the generic acronyms and like classic industry norms. I forget what they were for like cloud security, but it's just like, we don't, we're not this thing. We're whiz. Here's what we do.

• 28:52Speaker 00

  They are definitely a company that, that zags when others zig. I still have my whiz socks, which have these beautiful eight bit characters on them. Their branding really stands out in the sea of sameness in SaaS conferences.

• 29:06Lenny Rachitsky?

  Okay. There's something I heard that you did at Stripe that I wanted to ask you about that worked really well. When you came into Stripe, you looked at all of the biggest customer support issues and you turned those into docs to help people serve themselves. Can you just talk about that insight and the power of doing something like that?

• 29:22Speaker 00

  Yeah, this was a great practice that existed at Stripe even before I joined, which is all new hires would do a support rotation just to build empathy with our customers. So users first was a very core operating principle for the company. And we spent about 20% of our time collectively talking to customers, talking to users, talking to non-users to understand their needs, their gripes about the product. And that tradition, I think, continues to today. The support rotation specifically was such a fantastic fountain of understanding, hey, like, these are the areas that people are confused about. Again, I kind of mentioned the sort of cheat code of talking to your customers and using the language that they use to describe their problems as a shortcut to fantastic product

• 30:03Speaker 00

  marketing and messaging, because it, it really tells you what are their pain points and how can you meet them where they are. You want them nodding their heads along as they're reading your landing pages. And so when I was doing the support rotation, there were thematic things that kept coming up. You know, people were asking, hey, do you process subscription payments or recurring payments? Or can I pay people out with Stripe? And I was like, of course you could, but there's no reason you should know that because we don't tell you anywhere. And so that ended up being a stacked ranked backlog of landing pages that we produced that just educated people. And this is really important when you have strong top of funnel demand and potentially not as many people and you're not trying to

• 30:44Speaker 00

  scale your teams linearly. Having those educational resources, especially for developers, a fantastic marketing funnel sometimes doesn't look like talking to sales. It often never looks like talking to sales. It looks like a self-directed educational experience. Even the sales process ends up being very consultative, typically with very technical folks on the other side. So yeah, that was a great way and a great program to figure out what content we should focus and prioritize.

• 31:12Lenny Rachitsky?

  These are really cool, just little ways as a new marketing person, you can add value really quickly is kind of what I'm taking away.

• 31:21Speaker 00

  Talking to customers is at the top of the list.

• 31:24Lenny Rachitsky?

  Today's episode is brought to you by LinkedIn Ads. One of the hardest and also most important parts of B2B marketing is reaching the right people. I'm constantly getting ads for products that I will never buy. And I almost feel sorry for the money that these companies are spending pitching me on their spend management software or some kind of cybersecurity solution that my one man business just does not need. When you're ready to reach the right professionals, use LinkedIn Ads. LinkedIn has grown to a network of over 1 billion professionals, including 130 million decision makers. And that's where it stands apart from other ad platforms. You can target your ad buyers by job title, industry, company, role, seniority, skills, even company revenue. All the professionals

• 32:09Lenny Rachitsky?

  that you need to reach in one place. Stop wasting budget on the wrong audience and start targeting the right professionals only on LinkedIn Ads. LinkedIn will even give you $100 credit on your next campaign so that you can try it for yourself. Just go to LinkedIn.com/podlenney. That's LinkedIn.com/podlenney. Terms and conditions apply. Only on LinkedIn Ads. There's something else that I know that you're a big advocate of, which is internal reviews and just making sure everyone's aligned, which I think a lot of people, especially startups, try to avoid like, let's just move fast. We don't need to like have all these meetings or review stuff, but I know you're a big advocate of that. Talk about why that's so important.

• 32:48Speaker 00

  Yeah, this is a hill that I would die on, which is that good process or sufficient process is actually something that speeds up a company rather than slow it down. It steps from this idea that we talked about a little bit, which is that marketing is an extension of your product. It's the first touch point your customers have with your product. And ideally, you're setting expectations there in terms of what they should expect once they sign up for the product or commit to a contract and start using it within their companies. And when I think about that, consistency is really, really important. The other part, the other facet of why process is important is because, especially as you're in hyper growth companies, scaling teams is part and parcel, like what you're trying to do.

• 33:30Speaker 00

  And when you bring in someone new, you want them to be just as self sufficient as somebody who's been at the company for two years. So in your second week, can you be as successful as someone who's been at the company for two years? And the reason that I have that principle in mind is because it makes you kind of break out of your shell of, I've been at this company for some time now. I understand the unspoken rules of the organization. I've built up enough social capital that I can withdraw from to get something done. And I know, you know, which conference room to stand outside of to get the founder to review a piece of content before it goes out the door. That is not scalable. That is not sustainable.

• 34:12Speaker 00

  And so if you want somebody to be successful and contributing member of the organization very, very quickly, setting up some of these processes with the intention of trying to help them navigate how to go from idea to execution can be very empowering and powerful. Nobody wants to do the wrong thing. They want the guardrails to understand what great looks like at the company.

• 34:33Lenny Rachitsky?

  Can you speak more about what this looks like? Say a startup wants to start implementing something like this.

• 34:37Speaker 00

  Two simple processes that you could put into place today is one, set up a forum called marketing review. This can be a live meeting that you host for an hour a week, or it can be a Slack channel where people are posting things async, or even an email alias where things get sent to. Have that be transparent to the rest of the organization so anyone in the marketing team, anyone in the product organization can join that forum. What that does is it creates a fishbowl where you see sort of what are the themes that come out when somebody reviews a piece of content? Is it, are they looking at the strategy? Are they looking at the audience? Are they looking at the words? Are they looking at the sort of design approach? So you learn through osmosis of looking at some of these discussions.

• 35:20Speaker 00

  And then I would say, don't overdo it. I would say there are probably two checkpoints in a program that are really important to get aligned at. One is the 20% review. A 20% review is a strategy review. What are we trying to accomplish? Who are we trying to do it for? And what is the rough approach that we're going to take? If everyone feels comfortable with that, you come back at the 80% mark where you've done a lot of the work on the artifacts, the different types of teams that have to be involved. And how do you take something to market in the first place? And the reason that I say 80% is sort of critical because if you come in at the 99% mark and you're just looking for a rubber stamp of approval, you don't really have the slack in the system to be able to make any changes, then that review was worthless.

• 36:03Speaker 00

  So come in at the 80% mark where you can still make some substantive changes before it goes out the door. And that serves the purpose of consistency so that, you know, your brand is showing up in a consistent way to the audience. And two, it helps the rest of the organization learn from each other.

• 36:19Lenny Rachitsky?

  There's almost this unspoken element of what you're describing that I want to dig into a little bit, which is the, the need and value of having consistent and high quality marketing, communication. Why is that important? There's always this talk of just like move fast, break things. We're going to be scrappy. We're not going to be obsessed with like perfect quality of our, I don't know, websites and emails. Just like, why is that important? Why do you value that? Why should companies maybe value that more?

• 36:45Speaker 00

  It's funny because the companies who value velocity actually do value their brand just as much. But oftentimes they think of these as two siloed, separate initiatives that they have to put their headspace and calories towards. And I actually think they are not mutually exclusive. They are actually very interconnected. And so when you understand the consistency of your brand, it actually empowers the organization to move faster because you kind of understand how you want the brand to show up in the world. What is that experience that you want your customers to come away with when they interact with your brand? And the brand is not just marketing artifacts. It is your product experience. It is

• 37:29Speaker 00

  how your customer support team talks to them, how they resolve tickets. Are you getting passed between a bunch of different teams or is someone just resolving your ticket right away? It's the experience that they have for candidates when they come to recruit at your company. So all of these variety of touchpoints that touch so many different organizations and teams within your organization, they are the amalgamation that makes up your brand. And so if you think of these two things as separate silos, you are optimizing for entirely the wrong thing.

• 38:01Lenny Rachitsky?

  I've very viscerally learned the power of brand doing my newsletter. Like I so fear doing something very wrong in my newsletter. It's like saying something that's completely off or having something broken or sending an email by accident to everyone that's not ready. Like, I just feel like once I break that, just there's so much power and trust that people have built for what I share. And there's so much power that comes from that trust. Like if I launch a new podcast, you know, people will assume it will be good if they trust what I do and I maintain high quality. And so it's just like a constant fear I have now of hurting, of breaking that trust.

• 38:40Speaker 00

  Yeah, I mean, whether it's, uh, it's fear that drives you is questionable because I think it's also a commitment to your craft. But I think that's exactly right. Like a brand is an expectation that you create within your audience.

• 38:57Lenny Rachitsky?

  And, and to what you said, if you have a strong brand that people trust, everything gets easier. You pitch them a new product. Oh, I'm gonna go check. Like if Stripe's like, oh, we have a new billing service. Oh, I bet it'll be awesome because it's Stripe. Or if OpenAI launches something, you know, so that's, it just makes life easier if your brand is strong, if there's trust.

• 39:16Speaker 00

  Yeah. And you've got to take that responsibility seriously because even with something like Stripe, we know that people are going to come try out things that we put out the door. And so we wanted to make sure that that met up to people's expectations. And same thing with OpenAI. When we launched something, Even though we were trying to be first to market and that velocity was so important for the company, oftentimes it also came with sometimes putting the brakes on to kind of understand how can we improve the quality of the experience, how can we make sure that it is safe. So there were different criteria at the two companies, but a similar ethos overall for the brand experience that we wanted people to experience.

• 39:55Lenny Rachitsky?

  Let's actually come back to OpenAI. How long were they around until, before you joined? It was like many, many years, right?

• 40:01Speaker 00

  Many, many years. So OpenAI had been around for almost a decade as primarily a research organization. They had launched ChatGPT about a year before I joined. And so that was the first foray into saying, hey, our, our work is not just announcing research breakthroughs, it is about putting products into the market.

• 40:19Lenny Rachitsky?

  So there's a few questions I want to ask here. When is just like, when is it time to bring in a Krithika? Like, when is it like, okay, we need help here. We're like a bunch of smart people doing great work, people have the product, but like, hmm, I think we need a marketing person that knows what they're doing.

• 40:33Speaker 00

  I think the first criteria is having tremendous product market fit, which is really important because you're throwing fuel on the fire and you might be throwing different types of fuel on, on your particular fire. So one pillar for marketing that you have to think about is product marketing. So if you have a high velocity engineering organization and product organization that is putting out a lot of different features and your customers aren't able to keep track, maybe the engagement's not so high for some of the newer features versus some of the core features that you had in the past, a product marketer can really help bring a discipline of launch excellence and customer engagement. Differentiation in the market, how are you positioning the product?

• 41:14Speaker 00

  The second pillar for me is demand generation. So if you have much more of a sales-driven buyer journey in motion, how are you bringing the demand engines to bear so that your lead generation, your pipeline generation is staying really strong and solid? Or you might want to think about brand, right? Like you might want to think about community development as a big part of what you're doing as a company. So it really depends, but I think in all of these, you found a spark of product market fit before you're really going for it. The second for me is that you're distinguishing enough between capital M marketing and lowercase m marketing. And this is an important distinction I've learned over the years, which is capital M marketing, the marketing team, the marketing function at the company.

• 41:58Speaker 00

  Is responsible for those channels and artifacts and engines that are driving the funnel for the company, but they are not the end all be all of like the discipline of marketing. And that's where the lowercase m marketing comes in, which is what do you stand for as a company? What, what is the storyline that you're telling as a founder when you're talking to the press, to the, the larger business community? And then, you know, it really is a whole company motion where the product team is thinking about, how are we going to market? What are we going to market with? The sales team is figuring out what is the right ICP, the right customer profile that decision makers are, that we need to be reaching.

• 42:39Speaker 00

  And then it is this entire joining of the organizations to make that happen really effectively.

• 42:47Lenny Rachitsky?

  Yeah, I think along these lines, there's a reason Brian at Airbnb merged marketing and, or product marketing and product management, however much that actually happened or not. But that the intent is.

• 42:57Speaker 00

  I would be so curious to see a follow up a few years on, on how that's been going.

• 43:01Lenny Rachitsky?

  Yeah, that's a, okay, let's have Brian back to talk about that. That'd be really interesting. I wanted to actually ask, so an interesting thing is happening with chat GPT versus Claude. And if like, it's so interesting. Claude is arguably better at many things at code, at least at this point. You know, things are always changing. People, it seems to be a better writer in a lot of ways. People prefer it for writing, but it's just like chat GPT is just dominating. It's like, that's what people associate with AI now is just chat GPT. It's just like caught my mind share globally. What is it, do you think that allowed chat GPT just to be that? Is it just first mover advantage? Is it some kind of other element? Is it just best been better longer? Like something really interesting is going on there.

• 43:46Speaker 00

  One of the things that comes to mind is the orientation when it comes to large language models and AI in general is that we're just at the very beginning innings of this whole. Paradigm shift. And so every single week, there's a new breakthrough in AI that comes out from some lab or the other. There's this one upmanship on, you know, point changes and eval numbers and so on and so forth. But I think to customers, the users of the product, the things that make it delightful are the same things that make any product delightful. And there's a sense of loyalty that builds up over time when there is a shorter and smaller delta between your expectations and your reality.

• 44:30Speaker 00

  And where those expectations are exceeded, it is accretive to the brand and your loyalty to the product. And where there is a negative delta, that tends to be something that it really detracts. I guess, long story short, what I'm trying to say is that all of these companies have to think in a much more long-term oriented fashion because it's not about a race of the best chatbot and the best outputs. It's about how does AI become a positive force for humanity? And so that's going to take a lot of change management and a lot of collaboration between a variety of different organizations, rather than just the companies themselves and the product experience itself, because it's going to permeate every aspect of our lives, our personal lives, our academic lives, our work lives.

• 45:15Speaker 00

  And so to make that transformation happen, my hope is these companies are not super focused on just their competition and one-upmanship, but rather thinking about the paradigm changes that need to happen for our society at large.

• 45:30Lenny Rachitsky?

  It does feel like they are taking that responsibility really seriously, but it is a massive responsibility. Before we leave OpenAI, I like, it feels like it may be the most impactful, important company in the world right now, just because they're seem to be at the furthest edge of where AI is going. And so it's just such an interesting place to study. So let me ask you this, just like as a person working there, what's like something people may not know that's a like a wonderful, positive element of how OpenAI works? That's just like, oh, that's super interesting. And then what was maybe a challenge of working at OpenAI?

• 46:08Speaker 00

  A surprising thing that surprised me at the company was just the warmth and intellectual curiosity of my peers and leaders at the company and truly the sort of

• 46:20Speaker 00

  Commitment to the mission of making artificial intelligence that benefits all of humanity was not just lip service. It was something that was embodied day to day. The sort of questioning that happened, the sort of pressure testing that happened, the rigor with which products were developed, go to market strategies were developed, was bar none. And so that's something that I really admire and it was a privilege to be a part of that organization. I think challenging, of course, is just being at the eye of the storm, right? The eye of the eye of the hurricane. And so all eyes are on OpenAI at all times. And I think that is a good thing because of the ramifications of the product.

• 47:00Speaker 00

  But it also really raised the stakes in terms of how we operated and with what scrutiny, everything that we did was looked at with.

• 47:09Lenny Rachitsky?

  Do you recommend that sort of experience for people? Because I imagine work life balance wasn't great. I imagine there was a lot of stress and worry constantly. Who's like the right person? Like, when in your career is this a sort of gig to take on versus not?

• 47:25Speaker 00

  I'm a big believer of what Claire Hughes Johnson, who was COO at Stripe, used to share with us, which is there is a concept of a work life blend and sort of making sure that you're working at a company that has three components. I think first and foremost is always people. So are the people that you're surrounding yourself with ones that push your thinking, who are kind, who are genuinely interesting people to spend your hours with? Because you're spending a vast majority of your time with them. The second to me is product, right? Like, do you go to sleep thinking about the product, waking up, wanting to put it into the hands of more people because you know it is going to be good for them or useful to them? That's something, you know, I'm not one of those marketers who can pick up any product and market it.

• 48:10Speaker 00

  I have to have that conviction behind the product itself. And then the third is sort of potential, right? Not just potential for the company to do well, but potential for your discipline to have an impact on the trajectory of the company. And so when you have that kind of potent combination, it can really change your perspective on what's draining, what's energizing. But being very self-aware of what gives you energy is also very helpful to align with the needs of the company also.

• 48:41Lenny Rachitsky?

  Let's shift to talking about Thrive, which is where you work now. And I talk about what your role is. And what's interesting, I think, about this role is you get to work now with a bunch of different startups instead of go really deep with one. So share what you do there. And then what are some things you've learned there so far from a perspective of marketing?

• 48:59Speaker 00

  Yeah, surprisingly, more people know about Thrive these days than used to even just a few years ago. And Thrive is a very unique type of investment company. And sometimes when I made the leap, people used to ask me, oh, was this always in your ambition to make the leap into the investment side of the house? And I can honestly say it wasn't. But I think being at a firm like Thrive really gives you a very different perspective. And it strengthens your ability to be a stronger operator, whether that's in marketing or go to market or strategic finance or whatever other pillar within the company there is. Yeah, Thrive's mission is to be the most meaningful partner to founders. And so there's a lot of high concentration, high conviction investments each year. And Thrive is also unique in that it's a network of builders.

• 49:43Speaker 00

  And so they are really pulling their investment strategies from having been founders themselves. So my role at the company is to help our entire portfolio with all of their marketing needs. So sometimes it means being interim CMO for some portion of time until they find a great leader to fill that seat. Sometimes it means pressure testing their strategy and making sure that their growth targets are ambitious enough. Sometimes it means looking at a Figma file for a landing page that's going out the next day and making sure the words are as good as they can be. And that variety across a bunch of industries, a bunch of stages of companies, everything from a company that hasn't even been incorporated yet, all the way to Databricks and Stripe and OpenAI

• 50:27Speaker 00

  when it comes to the types of organizations that we work with. And then, yeah, the variety of domains can range from consumer to healthcare to defense, to B2B SaaS, to AI. So It is a variety pack in the best way possible.

• 50:43Lenny Rachitsky?

  And so what are the, what are some things you've learned so far? Cause I imagine this is a very different experience. That I don't know, especially things you've like, like changed your mind on even. Working with a bunch of companies, early stage versus.

• 50:57Speaker 00

  It's a really different method of operating. And so when you're in the leadership role for marketing within a single organization, you have at least a medium term North Star in terms of what your teams are trying to drive for the company. And as much context switching as there might be, there is still one company, ideally one product, one buyer journey. That hasn't always been the case, especially with OpenAI and Stripe, but. And it can span B to C, B to B, B to D. Thrive is very different in that if you want to be a meaningful partner to the founders, you cannot just jump from 30 minute call to 30 minute call to 30 minute call. You have to go deep to understand the context.

• 51:39Speaker 00

  And if anything, it's really underscored my ethos that you as a marketer, the best thing that you can bring to the table is your adaptability and flexibility. So to really diagnose and not just try to spot patterns and themes and playbooks for these companies, but rather be very deep in the trenches with them to understand their unique context, their unique concerns, their unique characteristics and their values and what they want to bring into the world. The, the reason that they want to work with Thrive is not because we are bringing our past experiences to the table, but rather because they're trying to do something new that has never been done in the world. And so those are the engagements that are the most exciting is that you're building

• 52:21Speaker 00

  and going into uncharted territory alongside these founders.

• 52:26Lenny Rachitsky?

  I bet they're all like, Krithika, what is the playbook for growing this B to B SaaS company? And you're like, no.

• 52:29Speaker 00

  And I say, there is none.

• 52:31Lenny Rachitsky?

  Damn. But we got, we got the framework that we talked about. Okay. I want to zoom out a little bit and talk about just career advice for marketing people. Whether it's early stage or later stage, you have this concept, the chameleon CMO. Talk about that and why that's important for marketing folks to think about.

• 52:48Speaker 00

  Yeah, the conventional wisdom for many CMOs is to be like a T-shaped marketer. And what that means is go deep in one of these pillars that we talked about. Product marketing, demand marketing, brand marketing. And that kind of becomes your calling card in the world. Like if a company needs brand expertise, they go for this kind of flavor of CMO. Or if a company needs to really grow their pipeline or their demand gen or their consumer growth, they go for more of like a demand and growth oriented CMO. And I think this chameleon CMO concept is is a bit of a novel one in that, again, I think modern marketing leaders have to be really good at a bunch of different things. They have to be very analytical.

• 53:32Speaker 00

  They have to be best friends with the data science pod because they need to understand the impact of their marketing. They of course have to bring creativity, but it is in service to the buyer journey. It is in service to revenue goals and goals that they share with the sales team or the product team and so on. So, marketing operating in a silo is no longer a real possibility. So, the ability to diversify your interests, maybe going from T-shaped to comb-shaped is probably the right approach here so that you can go deeper in different domains when it is useful for the company through the diagnostic that you do.

• 54:08Lenny Rachitsky?

  That sounds very hard. I love this meta visual of the comb shape. It sounds like I have so much to learn, so many little skills to build.

• 54:16Speaker 00

  This is where AI can come in handy. You know, some of the most like brand marketers can become very analytical with the support of a tool like ChatGPT. If your eyes glaze over when you look at giant dumps of CSVs, it's it's nice to have a partner that is nonjudgmental to kind of push your thinking and to help you understand the details of the data behind the brand work that you might be doing or vice versa, like if you're a very creative. Product marketer, a very analytical growth marketer, you can work with ChatGPT to be more of a brainstorm partner and really push your thinking on the creative side. So I think becoming a non just T-shaped marketer is getting a little bit easier.

• 55:00Lenny Rachitsky?

  Hmm, that's such a good point. A good segue to an AI question. We got to talk about AI. One of your former colleagues, Kevin Garcia, wanted me to ask you something. He suggested ask you about taste and creativity in AI. So he said that you're one of the best writers that he's ever worked with. You combine technical backgrounds with creative taste. You do pottery, he shared. And you're a voracious reader. And he wanted just to poke at what you think about just how tasting creativity and writing change in the era of AI.

• 55:31Speaker 00

  I think it's going to become so much more important. First of all, I will say I am not a ChatGPT hyphen person. Like I was an M-dasher well before it became a ChatGPT.

• 55:41Lenny Rachitsky?

  Me too. I hate that, that just for people don't know, like people are filtering out M-dashes, right? Because they think ChatGPT is the only thing using M-dashes.

• 55:49Speaker 00

  I don't know what to do about it because this is such a core part of my identity, but.

• 55:54Lenny Rachitsky?

  That's a big statement.

• 55:58Speaker 00

  To take a step back, though, you know, I think if anything, taste is going to become a distinguishing factor in the age of AI. Because there's going to be so much drivel that is generated by AI, can be generated by AI, that power is at anyone's fingertips. But truly, the companies that are going to distinguish themselves are the ones that show their craft, that they show their true understanding of the product, the true understanding of their customer, and connect the two in meaningful ways. If they can use AI to augment their efforts to make that happen, that's better than than subsuming their efforts. So to build taste, you know, there's, there's plenty of past episodes that you yourself have recorded that get into building that work, but.

• 56:41Speaker 00

  To me, that is going to be a real differentiator for not only great marketers, but great companies to just to stand out in the field.

• 56:50Lenny Rachitsky?

  There's a concept that I love that recently I learned from Guillermo at Versal. He calls it exposure hours as a that's when I asked him how to build taste. And that's kind of a value they have at their company is just get increase your exposure hours to great stuff because that is how you build taste. I love that. It's such a simple, actionable thing you can do.

• 57:09Speaker 00

  Yep. At Thrive, we have this share channel, which is just sharing things that we're seeing out into the world. It's not particularly deal flow news or competitive news or anything like that. But it is things that we have seen that resonated with us for whatever reason.

• 57:23Lenny Rachitsky?

  Along these lines of not over relying on chat GPT AI tools for writing and creativity, it feels like there's going to be a big issue with people just starting earlier in their career where they just like never learned how to do the thing. And they just rely really heavily on chat GPT and tools like that to write, to email, to communicate well. I guess, is there, do you have any advice for folks that are early career, just like how to find that balance of over not over relying, but still leveraging these tools?

• 57:52Speaker 00

  I think there's two schools of thought here. One is that sort of the domain, the discipline itself stays static and the way that you approach it changes over time. So whether you're going at it in a manual way or an automated way or an AI augmented way. But I think the other school of thought, which I more believe in is that the discipline itself is changing. And so what it means to market a product, what it means to show up as a fantastic operator is in and itself changing. And so if you're not leveraging some of these tools, you will be putting yourself at a disadvantage. But understanding the underlying mechanics, you know, this is why I would still be a very firm believer in in STEM education is that you understand the fundamental concepts.

• 58:36Speaker 00

  And then you can have a choice and optionality in how you decide to apply those concepts. But the concepts themselves have to be there in the foundations.

• 58:46Lenny Rachitsky?

  Yeah, easier said than done because there's all these tools now and you're just like, hey, I need to write a report for school. Like, I guess I could just, maybe this time I'll just ask chat GPT to help me with this one.

• 58:56Speaker 00

  Yeah, the mindset of learning has to be maybe the one that. We have to really imbue as a value because being of that growth mindset, you, if you go to school just to earn the grades or to finish the coursework, it's a very different mindset than if you go to school to learn those concepts and to understand how to apply them.

• 59:19Lenny Rachitsky?

  That's something that stuck with me from my chat with Toby Luckey from Shopify. We were chatting about just like, what is the most important things to incubate in your child? And his answer I loved, which is just, which curiosity.

• 59:32Speaker 00

  I love that.

• 59:33Lenny Rachitsky?

  Yeah. And that's what you're kind of speaking to is just like, if you're curious about learning, you'll almost avoid some of these things or you'll use these tools in a really interesting way just to learn things more deeply.

• 59:43Speaker 00

  And that stays with you into your career, right? Because you can either go into your career trying to get to that next ladder in the promotion rung, or you can get there to bring a genuine curiosity to what makes us different? What makes our customers tick? And how do we find those unique insights that can unlock something that nobody else has?

• 1:00:04Lenny Rachitsky?

  That reminds me, I wanted to come back to sort of close out our conversation. I wanted to come back to pricing strategy. I have that in my notes here and I haven't gone back to it. So let me just, let's focus on the AI and pricing strategy. Just like, say someone is trying to figure out pricing for their product and they have some kind of AI product. What are some tips, some piece of advice to think this through? Any general frameworks you use?

• 1:00:25Speaker 00

  Again, there's no playbook. So I feel like it's such a non-answer, but I think the real answer is experimentation. And we found this firsthand multiple times at Stripe, but also at retool. I think there was a very visceral example where we decided to bring our free product into the hands of more users and sort of what was available in the free plan. And then there was another one that we tested out as a pricing function where we decided to do. Something quite controversial, which is to take the thing that our sales team was gated on, a self-hosted version of Retool, and made that available self-serve to anybody who wanted it. They didn't have to talk to a salesperson. And that kind of blew up the funnel, right? Because the amount of pipeline that the sales team saw had diminished considerably,

• 1:01:09Speaker 00

  but it also helped them focus upmarket on higher ACV deals. And so that trade-off was really hard to make. And so the only way we could do it was through experimentation and piloting to build conviction. So I would say AI is no different in that you kind of have to test the market to see what works. Is it a seat-based model? Is that where people are deriving value? Or is the way that they speak about the value of the product something quite different? Is it hours saved? Is it the amount of things that they could do now that they couldn't do before? And so there might be a metric there to go off of. And I don't think anyone solved it. Like, there's, especially with agents coming into the play,

• 1:01:51Speaker 00

  like how you pay for AI workers is going to be very different. You know, what is that unit of completion for things like code generators is going to be, it's going to be a wild, wild west before we come up with something that is as internalized now as seat-based pricing or usage-based pricing.

• 1:02:10Lenny Rachitsky?

  Wild indeed. I want to actually follow this insight you had around Retool. That's really interesting. So you had, what was, so you opened up self-hosted Retool. What was the insight there? Because this might be useful to people that convinced you to play with that. Seems like a big deal change to how you price and do trials.

• 1:02:30Speaker 00

  There were two guiding principles here. One is, do people actually want to talk to sales before they get a self-hosted thing? And sort of like the SSO tax, right? Like, is that really the thing that you want to get your value on? And so that was one. And so we saw a lot of demand from smaller customers that still wanted self-hosted for a variety of reasons, because they worked in regulated industries, or they worked with very private data and PII. And so it wasn't just something that was, hey, if you have 10,000 employees at your company and you're an enterprise, you want self-hosted. It was that for a variety of different reasons, regardless of your company's size, you might want self-hosted. So that insight kind of led us to say, hey, where is the delineation here? Because the

• 1:03:11Speaker 00

  sales team should be talking to larger customers, landing larger deals. And so to align those two was one of the driving principles.

• 1:03:19Lenny Rachitsky?

  Awesome. Okay. Two final questions before we get to a very exciting lightning round. I'm going to take you to a couple of recurring segments on this podcast. The first is AI Corner. And with AI Corner, what I try to get to is some way that you have figured out to use an AI tool in your work to do better work, to do faster work, to be more efficient. Is there something there that you could share? And if not, that's also totally cool.

• 1:03:46Speaker 00

  Ooh, it is, it is hard to pick because there's not many things I don't use AI for these days. And oftentimes, it's a catalyst and an accelerant to the work that I'm already doing. But I think it can actually unlock my ability to talk to dozens of companies across the Thrive portfolio in any given week. And the ability to get deep on their context, their, their environment, their competitive landscape, we can do that because of the tools and the products that Thrive has invested in from an engineering perspective. So we have internal tools that are driven with AI that give us a lot of insights and access to expertise for these companies. So we can show up as more meaningful partners in a day-to-day basis.

• 1:04:29Speaker 00

  So I think the ability to mix AI tooling that accelerates work that you're already doing, and then AI-based tools that unlock superpowers that wouldn't otherwise be available to you unless you're going deep into, you know, Google Groups archives or talking to people across the organization to pull out things that are inside of their brain. That kind of institutional knowledge being made more accessible by AI is actually more powerful sometimes than, than the tools themselves. And in fact, even at OpenAI, it's one of the things that we advised most enterprises to invest in first is their own operational efficiency, rather than just the AI magic

• 1:05:11Speaker 00

  dust they could sprinkle on top of their product experience for their customers.

• 1:05:15Lenny Rachitsky?

  Awesome. Okay, final segment of the podcast we call Fail Corner. And the idea here is we have all these amazing guests, all these super successful people on the podcast, all these stories of epic wins and nothing but success. And I think in reality, that's not the case. And it's important for people to hear that things aren't always up and to the right and always win, win, win. Is there a story from your career you can share where things didn't work out? And what you learned from that experience?

• 1:05:44Speaker 00

  Again, this question is hard because there are so many things to choose from as potential examples here. And you're absolutely right, Lenny, in that like most careers are not the sort of linear journeys that are reflected on somebody's LinkedIn profile. Now, I'll talk about a fantastic success, which is called Stripe Relay, which you probably, I'm just kidding, because nobody remembers that. It was ahead of its market. We launched it back in 2014. It was supposed to be the platform with which e-commerce companies would tap into social commerce, the buy buttons, if you remember that. And it launched to a lot of fanfare, but then eventually failed. Like it didn't produce the sort of revenue or the numbers that we had expected.

• 1:06:28Speaker 00

  And the understanding here was that as much as one side of the marketplace, or you might have some conviction that you need to put something into the market for a particular moment in time, the timing of the market really matters. And the timing of multiple parties coming together to make a platform work really matters. And so the learning here was like, we hadn't gone deep enough into the market dynamics. We hadn't done enough user research. Did people really want this? And if they did, what were their alternatives? What was the stacks that they were operating in? And would they adopt a net new tool versus one that integrated into existing systems directly? Like their e-commerce inventory management systems and so on.

• 1:07:09Speaker 00

  And so for that reason, I think, again, it was ahead of its market and ahead of its time. But A clear flop regardless of the effort that we put into that launch.

• 1:07:22Lenny Rachitsky?

  This reminds me of when Kevin Weal was on the podcast talking about Libra, which was this cryptocurrency project that Facebook ran. And he's just like, okay, that was a terrible time to launch something like that where people trusted Facebook the least in history. And now may be a good time to try something like that, basically a cryptocurrency platform to send money internationally for free. What a, what a dream that would be. Okay, Krithika, is there anything else you wanted to share? Or maybe something you wanted to re-mine people of from what we've talked about? Just to leave folks with a final nugget before we get to our very exciting lightning round.

• 1:07:55Speaker 00

  If, if there's one thing that folks take away, I hope it is that they know that there isn't one clear answer to any of the marketing problems. It, it seems like there's a playbook for everything. There's a framework for everything. But the reality is the work is, is hard. You have to spend the hours and the time to really understand your customer. And there is no replacement for that. And there isn't going to be even with the advent of AI. And the other part of it is to deeply understand your product as well. Like what are you bringing to the table? And not just your product, but your company's values, your unique approach that you're bringing to the table. And really be intentional and thoughtful about that because

• 1:08:37Speaker 00

  in the absence of that, nothing is going to be a substitute to bring that combination of ingredients together.

• 1:08:45Lenny Rachitsky?

  With that, we've reached our very exciting lightning round. We have five questions for you. Are you ready?

• 1:08:51Speaker 00

  Hit me.

• 1:08:52Lenny Rachitsky?

  Here we go. What are two or three books that you find yourself recommending most to other people?

• 1:08:57Speaker 00

  On the professional side, one book that I recommend to most people is April Dunford's book on positioning called Obviously Awesome. She does a great job breaking down how to position a product from scratch if you've never had to do that.

• 1:09:11Speaker 00

  And she's just so great for her real talk. So really highly recommend that. And then I love. Fiction. So I would say one of the best reads in the last couple of years has been Madeleine Miller's Circe, which is a retelling of a Greek myth. So lyrical prose, beautiful writing, highly recommend.

• 1:09:32Lenny Rachitsky?

  Love the combo. April Dunford, we're huge fans of her on the podcast. She's been on twice. I think her book is in my background. We'll link to her episodes.

• 1:09:39Speaker 00

  And mine.

• 1:09:40Lenny Rachitsky?

  Oh, wow. Okay. So cool. Yeah, she's the best. Okay. Next question. Do you have a favorite recent movie or TV show that you have really enjoyed?

• 1:09:48Speaker 00

  I'm really late to the game, but I'm finally catching up on Severance. So no spoilers, but I'm about halfway through the first season.

• 1:09:54Lenny Rachitsky?

  Wow. Okay. It's hard to avoid the spoilers. But yeah, keep going. It's amazing. Do you have a favorite product you recently discovered that you really love?

• 1:10:03Speaker 00

  Granola for meeting notes. I love taking meeting notes as a way to stay engaged in the conversation and to pay a lot of attention. But I also know I'm like furiously typing away. And so the ability to augment my notes and bullet points has been a game changer.

• 1:10:20Lenny Rachitsky?

  That's two guests in a row that said granola. And I'll give a plug. You get a year free of granola if you become an annual subscriber of my newsletter for not just you, but your whole company up to some limit. Check out Lenny's newsletter.com and click bundle and sign up and get granola. So cool.

• 1:10:36Speaker 00

  Happy to help, Lenny.

• 1:10:38Lenny Rachitsky?

  It's helping granola and me, I guess. Yeah, it's great. Okay, thank you. Two more questions. Do you have a favorite life motto that you find useful in work or in life?

• 1:10:49Speaker 00

  My teams have now gotten tired of me saying this, but I say it all the time, which is the delta between expectations and reality is the function for unhappiness. And so it is much easier to change expectations than it is reality. And so I tend to spend a lot of my energy making sure that expectations are set, not just with customers when it comes to our external marketing, but internally with stakeholders, project partners, and even within the team, so that they understand what are some of the trade offs that we're making or why we're making certain decisions. So I could not espouse that philosophy enough.

• 1:11:25Lenny Rachitsky?

  I love that this isn't, because I think when people first hear that, it's about your own happiness. But I love that it's about other people perceiving how something did and setting their expectations correctly. Final question. Okay, we already talked about the M dash, but I want to ask you again. Like what I'm finding is, so the story here is basically people have discovered chat GPT is using M dashes a lot, which are like these long dashes that you have to use like special couple of letters on the keyboard to use. I'm a huge, I use these all the time and people are starting to like filter them out on Twitter. Cause they're assuming it's generated by chat GPT. There's like content that has M dashes. They assume isn't real. Will you continue using M dashes in spite of all this?

• 1:12:06Speaker 00

  I have begrudgingly reduced my usage of M dashes, but I, but you will not pry them out of my cold, dead hands if you, if you tried.

• 1:12:15Lenny Rachitsky?

  Oh man, me too. And it's like, I don't even know. It's like command options dash or something to even put it in.

• 1:12:20Speaker 00

  No, it's, it's option shift minus.

• 1:12:22Lenny Rachitsky?

  Option shift minus. I have to like type it. I can conceptualize in my head. Yeah. And then there's like actual rules for when an M dash is the right thing versus a, there's like a middle.

• 1:12:32Speaker 00

  M dash and the Oxford comma, the two core tenants of my toolbox.

• 1:12:36Lenny Rachitsky?

  Is it Oxford comma where you add the comma at the end or you don't?

• 1:12:39Speaker 00

  You keep the comma at the end.

• 1:12:40Lenny Rachitsky?

  You keep, okay, I'm all, I'm all for that too. It looks so weird without it. But there's also like another, like a shorter, not M dash, I guess it's called something else, right? There's like.

• 1:12:48Speaker 00

  End dash. Yeah, that's for ranges of numbers.

• 1:12:51Lenny Rachitsky?

  Okay, okay. I love that you know all this. Okay. Well, with that, Krithika, this has been so fun and so awesome. Thank you so much for being here. Two final questions. Where can folks find you online if they want to reach out, maybe work with you? And how can listeners be useful to you?

• 1:13:05Speaker 00

  krithix.com is where you'll find links to all of my online presences. And one of my personal missions this year is to meet as many of the up and coming marketing talents in the world. So anyone that you know is earlier career, ambitious, but really showing their impact at their organization. Please introduce them to me. I would love to chat.

• 1:13:26Lenny Rachitsky?

  And then what's the best way for them to reach out to you? Is it just on your website?

• 1:13:29Speaker 00

  Yes, please.

• 1:13:30Lenny Rachitsky?

  Amazing. We'll link to that in the show notes. Krithika, thank you so much for being here.

• 1:13:34Speaker 00

  Thank you for having me.

• 1:13:35Lenny Rachitsky?

  Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.