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

The Opening Introduction

Krithika Shankarraman: It seems like there’s a playbook for everything, there is a framework for everything, but the reality is you have to spend the hours and the time to really understand your customer.

Introducing the Guest

Lenny 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?

Krithika Shankarraman: 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 can 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?

ChatGPT’s Marketing Value

Lenny Rachitsky: If your advice is, “Don’t just copy what other companies do,” what should people be doing?

Product Management and Marketing Pair

Krithika Shankarraman: Put together a four-step process that has served me pretty well. The first step here is…

Consumer Tactics for Enterprise Products

Lenny Rachitsky: Today my guest is Krithika Shankarraman. 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 talk 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, 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 Krithika Shankarraman.

Krithika Shankarraman: Thank you so much for having me. I’m excited to be chatting.

No Ready-Made Playbooks

Lenny 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?

Krithika Shankarraman: It does. Not that I can take credit for it.

The Four-Step Diagnostic Framework

Lenny 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, why do you need marketing? It’s like the most magical thing in the history of the world. How much value does anything add to making it as successful? Can you just talk about just the value that a marketing person adds to a product like that that’s already incredible?

Analyzing Competition and Choosing Differentiation

Krithika Shankarraman: 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. I don’t know what it replaces. Should I be using search for this? Should I be using ChatGPT for this? 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 can do that. And yeah, maybe I should be using it for X, Y, Z reason in my own life.” And so I think you have 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 and conversion-oriented tactics that end up being in a playbook.

Lenny Rachitsky: So for folks that listen to this podcast, it’s a lot of product managers, product builders. A lot of them don’t have a lot of experience with marketing. I think it’s an important insight there of just, 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, here’s what you may not be good at and may need marketing help with.

The DATE Framework

Krithika Shankarraman: Yeah. When done right, product management and product marketing should be best friends, right? And you are 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 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.

Retool Case: From Passive to Proactive

Lenny Rachitsky: The other element of ChatGPT’s marketing success, I know that you spent a lot of time on the enterprise side, is just consumerish 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.

Krithika Shankarraman: 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 40 X-ed 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. I sat down with ChatGPT and I coded up a Python script that ended up functioning as our first lead qualification, lead-scoring model. That was used in production for way too long, longer than I’d care to admit.

Diagnosing Channels and Avoiding Vanity Metrics

Lenny 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 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 I don’t know if you just saw this, he just like, “At some point we will ask ChatGPT, how do we make money?”

Competitor Analysis: Stripe Connect’s Counter Strategy

Krithika Shankarraman: Yes. 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 kind of neatly fit the mold of SaaS-based pricing or seed-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.

Marketing Lessons: Retool to Stripe

Lenny Rachitsky: I will say, though, in terms of pricing, it feels like ChatGP, it works. It’s just like a monthly fee, talk 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 will this make money.” Now it seems so obvious.

Krithika Shankarraman: Truly was a research preview.

What Marketing Brought to Stripe

Lenny Rachitsky: And I remember Sam Altman just launched, “Here, check out this chat thing that we are trying with,” and then 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 kind of pointed out that with ChatGPT and OpenAI, there was no playbook, and you find that often people following playbooks don’t work. Talk about that insight.

Krithika Shankarraman: In my current role 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 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 was a combination of context, competitive landscape, and the overall sort of zeitgeist of when the company’s operating, how the company’s 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 and trying to follow in the footsteps of the tactics, you’re not paying enough attention to the inputs and, 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.

Three Chapters of Stripe Marketing

Lenny 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 there’s no playbooks that you… If your advice is, “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?

Continuous Diagnosis in High-Growth Companies

Krithika Shankarraman: Yeah. 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 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, “Hey, we really need to hire a demand gen leader. 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?”

That usually tells you very astutely, do you have product market fit? 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 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, we get a lot of interest, but once they’re in the room, they have a bunch of questions. They’re asking about, 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 throwing in more at the top of the funnel because you have a leaky funnel at the bottom. And so hiring a demand generator may be 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 analyzing your competitors’ approaches. So to me, this is not about being super laser focused on your competition because that leads to these local maxima rather than thinking about face 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 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 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. That bias of the sunk cause 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.

Unique Perspective from a Non-Marketer

Lenny 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 need to hire a demand gen person or a paid growth person or a SEO person, or I don’t know, content writer,” 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 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 inspiration and see where gaps exist. And then it 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. And then the final piece is just like, “Okay, here’s our path. Let’s test run some small scale tests to see if this would work.”

Krithika Shankarraman: Yeah. I’m a marketer through and through now. So I mean you got diagnose, D. Analyze, A. Take a different path, T. And experiment for the E. So it’s the DATE framework. I’ve just kind of coined it.

Turning Support Issues into Self-Serve Docs

Lenny Rachitsky: Oh, beautiful. Okay. We got a new framework hot off the presses. I love it. DATE, okay. So with differentiation, what’s your thoughts on saying you’re just a lot better or a lot cheaper?

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

Importance of Internal Reviews and Processes

Lenny Rachitsky: Awesome. Okay. So let’s go through an example of a company you did this with, and then this may take us to another company you worked at in the stories there.

Krithika Shankarraman: 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 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 demand engines was the name of the game. And here, 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.

Really, what you want to be looking at is your impact on either signups if you’re a self-serve product, 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 net new engines. So that was the diagnostic. When we looked at some of the competitors, we saw that they were doing a lot of content marketing. They were doing a lot of events programming. And we could’ve 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 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 types of event formats to see what actually worked best for us, and scaled the ones that worked and discarded the ones that didn’t.

Brand Consistency and the Value of Trust

Lenny Rachitsky: Okay, there’s so much here. So in the diagnose step, I think in kind of a between-the-lines piece of advice here is look at what’s already working. So you looked at, okay, 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.” There’s one more-

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

OpenAI’s Marketing Journey

Lenny Rachitsky: Got it. So they may be showing vanity metrics. 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 can we be doing differently?” Does it ever make sense just to do what they’re doing but do it better, or is that rarely a successful path?

Integrating Work and Life

Krithika Shankarraman: You still have to do something a little bit different. I recall a very specific example at Stripe where our product, Stripe Connect, which was made for marketplaces like Uber and Airbnb, where not only are you accepting money as a platform, you’re also paying out people on the seller side of the marketplace. 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 PayFac yourself. And a lot of the services, organizations, the consulting groups that were helping companies become PayFacs, 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.

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 PayFac without actually talking about ourselves as a PayFac 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. 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 there was 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.

Joining Thrive: From Deep Ops to Broad Vision

Lenny Rachitsky: Okay. And 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.

Krithika Shankarraman: I do not recommend that to anybody.

The Chameleon CMO

Lenny 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?

Brand Marketers Collaborating with AI

Krithika Shankarraman: 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, building that marketing function from the ground up, it really gave me the privilege of working very closely with our founders, 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. The experience really taught me the importance of deep product understanding as well. 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’re 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 yeah, the value of creating marketing artifacts that were deeply integrated with the company’s mission and the craftsmanship that went into the product was another lesson that I learned very deeply at Stripe.

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

Taste and Creativity in the AI Era

Krithika Shankarraman: Across my time at Stripe, marketings are very different purposes. And so I kind of see it in different epochs or chapters of my time at the company. The first chapter when I joined, our head of partnerships at the time, Cristina Cordova, handed me a Hackpad at the time, which is like a notion-

How Juniors Should Balance AI Tool Usage

Lenny Rachitsky: I remember Hackpad.

Krithika Shankarraman: Oh, yeah.

Pricing Strategies for AI Products

Lenny Rachitsky: It turned into Dropbox Paper.

Pricing Experiments for AI Products

Krithika Shankarraman: 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 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? 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. 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?

The AI Corner

Lenny 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 have a need for marketing and growth?

Krithika Shankarraman: 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. At some point, we really have to figure out how to scale our sales function. We have 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-shaped, people who could be flexible to those needs of the company.

The Failure Corner

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

Some Final Thoughts

Krithika Shankarraman: Yeah. If we did, we would still be talking about PCI compliance and payment gateways.

Lenny Rachitsky: There’s so much of what you share that reminds me of Raaz 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 your-

Krithika Shankarraman: Her first PM, actually. Yeah, Raaz is great.

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

Krithika Shankarraman: One thing it’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, “Is that really going to work? What developer is clicking on paid ads? Isn’t a better thing that we could be doing for them telling them to install ad block?” 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.

Lenny Rachitsky: The other really interesting corollary here is she was very big on avoiding the generic acronyms and classic industry norms, I forget what they were, for cloud security. But it’s just like, “We’re not this thing. We’re Wiz. Here’s what we do.”

Krithika Shankarraman: They are definitely a company that zags when others zig. I still have my Wiz socks, which have these beautiful 8-bit characters on them. Their branding really stands out in the sea of sameness in SaaS conferences.

Lenny 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?

Krithika Shankarraman: Yeah, and 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, these are the areas that people are confused about.”

Again, I kind of mentioned this 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 marketing and messaging, because 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. 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 rank backlog of landing pages that we produce 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 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.

Lenny 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.

Krithika Shankarraman: Talking to customers is at the top of the list.

Lenny Rachitsky:

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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 and especially startups try to avoid. Like, “Let’s just move fast. We don’t need to have all these meetings where people review stuff,” but I know you’re a big advocate of that. Talk about why that’s so important.

Krithika Shankarraman: 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 stems from this idea that we talked about a little bit, which is that marketing is an extension of your product. It’s the first touchpoint 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. 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 sort of unspoken rules of the organization. I’ve built up enough social capital that I can withdraw from to get something done. And I 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. 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.

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

Krithika Shankarraman: 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? 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.

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 it 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, and you don’t really have the slack in the system to be able to make any changes, then that review was worthless. 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 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.

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

Krithika Shankarraman: It’s funny because with 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 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 your company. So all of these variety of touch points 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.

Lenny Rachitsky: I’ve very viscerally learned the power of brand doing my newsletter. 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. 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. If I launch a new podcast, 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 breaking that trust.

Krithika Shankarraman: Yeah, I mean whether it’s fear that drives you is questionable because I think it’s also a commitment to your craft.

Lenny Rachitsky: Yeah, yeah.

Krithika Shankarraman: But I think that’s exactly right. A brand is an expectation that you create within your audience.

Lenny Rachitsky: And to what you said, if you have a strong brand that people trust, everything gets easier. You pitch them a new product. Like if Stripes like, “Oh, we have a new billing service.”

“Oh. Oh, I bet it’ll be awesome because it’s Stripe.” Or if OpenAI launches something. So it just makes life easier if your brand is strong, if there’s trust.

Krithika Shankarraman: Yeah, and you 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.

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

Krithika Shankarraman: 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 work is not just announcing research breakthroughs, it is about putting products into the market.”

Lenny Rachitsky: So there’s a few questions I want to ask here. When is a time to bring in a Krithika? When is it like, “Okay, we need help here”? Or, “A bunch of smart people doing great work, people have the product, but I think we need a marketing person that knows what they’re doing.”

Krithika Shankarraman: 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 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?

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? 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 and marketing and lowercase and marketing. And there’s an important distinction I’ve learned over the years, which is capital and marketing, the marketing team, the marketing function at the company 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 the discipline of marketing.

And that’s where the lowercase and marketing comes in, which is, what do you stand for as a company? What is the storyline that you’re telling as a founder when you’re talking to the press, to the larger business community? And then 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, that we need to be reaching?” And then it is this entire joining of the organizations to make that happen really effectively.

Lenny Rachitsky: Yeah. I think along these lines, there’s a reason Brian at Airbnb merged marketing, or product marketing and product management. However much of that actually happened or not, but the intention-

Krithika Shankarraman: I would be so curious to see a follow-up a few years on on how that’s been going.

Lenny Rachitsky: Yeah. Okay, let’s have Brian back to talk about that. That’d be really interesting. I wanted to actually ask, an interesting thing is happening with ChatGPT versus Claude, and it’s so interesting. Claude is arguably better at many things at code, at least at this point. Things are always changing. It seems to be a better writer in a lot of ways. People prefer it for writing, but it’s just like ChatGPT is just dominating. It’s like, that’s what people associate with AI now is just ChatGPT. It’s just caught mindshare globally. What is it, do you think, that allowed ChatGPT just to be that? Is it just first mover advantage? Is it some kind of other element? Has it been better longer? Something really interesting is going on there.

Krithika Shankarraman: 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 is a new breakthrough in AI that comes out from some lab or the other. There’s this one-upmanship on 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.

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. 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.

Lenny Rachitsky: It does feel like they are taking that responsibility really seriously, but it is a massive responsibility. Before we leave OpenAI, it feels like it may be the most impactful, important company in the world right now just because they 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 as a person working there, what’s something people may not know that’s a wonderful, positive element of how open AI works that’s just like, “Oh, that’s super interesting”? And then, what was maybe a challenge of working at OpenAI?

Krithika Shankarraman: 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 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 admired, 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 hurricane. So, all eyes are on OpenAI at all times, and I think that is a good thing because of the ramifications of the product. 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.

Lenny 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 the right… When in your career is this a sort of gig to take on versus not?

Krithika Shankarraman: 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? 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? I’m not one of those marketers who can pick up any product and market it. I have to have that conviction behind the product itself.

And then 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.

Lenny Rachitsky: Let’s shift to talking about Thrive, which is where you work now, and 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 for marketing?

Krithika Shankarraman: Yeah, surprisingly, more people know about Thrive these days than used to even just a few years ago. Thrive’s 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, 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 when it comes to the types of organizations that we work with. And in the end, 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.

Lenny Rachitsky: And so what are some things you’ve learned so far? Because I imagine this is a very different experience. I don’t know, especially things that you’ve changed your mind on even, working with a bunch of companies, early stage versus, what can I say?

Krithika Shankarraman: 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 it can span B2C, B2B, B2D.

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. 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 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 engagements that are the most exciting is that you are building and going into uncharted territory alongside these founders.

Lenny Rachitsky: I bet they’re all like, “Krithika, what is the playbook for growing this B2B SaaS company?” And you’re like, “Nope.”

Krithika Shankarraman: And I say, “There is none.”

Lenny Rachitsky: Damn. But 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.

Krithika Shankarraman: 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. 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 a demand and growth-oriented CMO. And I think this chameleon CMO concept 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. 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 interest, 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.

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

Krithika Shankarraman: Before AI can come in handy. Some of the most 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 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. 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 T-shaped marketer is getting a little bit easier.

Lenny Rachitsky: That’s such a good point. A good segue to an AI question. Hey, we got to talk about AI. One of your former colleagues, Kevin Garcia, wanted me to ask you something. He suggested I 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, you should. And you’re a voracious reader. And he wanted just to poke at what you think about just how taste and creativity and writing change in the era of AI.

Krithika Shankarraman: I think it’s going to become so much more important. First of all, I will say I am not a ChatGPT hyphen person. I was an em dasher well before it became a ChatGPT thing.

Lenny Rachitsky: Me too. Me too. I hate that. But just for people don’t know, people are filtering out em dashes, right? Because they think ChatGPT is the only thing using em dashes?

Krithika Shankarraman: Yeah, and I don’t know what to do about it because this is such a core part of my identity, but-

Lenny Rachitsky: That’s a big statement, the em dash.

Krithika Shankarraman: To take a step back though, 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 them subsuming their efforts. So to build taste, there’s plenty of past episodes that you yourself have recorded that get into building that work. But to me, that is going to be a real differentiator for not only great marketers but great companies to stand out in the field.

Lenny Rachitsky: There’s a concept that I love that recently I learned from Guillermo at Vercel. He calls it exposure hours. That’s when I asked him how to build taste, and that’s kind of a value they have at their company is just 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.

Krithika Shankarraman: Yeah.

Lenny Rachitsky: Yeah.

Krithika Shankarraman: And 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.

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

Krithika Shankarraman: 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, 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. So if you’re not leveraging some of these tools, you will be putting yourself at a disadvantage. But understanding the underlying mechanics, this is why I would still be a very firm believer in STEM education, is that you understand the fundamental concepts. 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.

Lenny 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. I guess I could just, maybe this time I’ll just ask ChatGPT to help me with this one.”

Krithika Shankarraman: 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, 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.

Lenny Rachitsky: That’s something that stuck with me from my chat with Toby Lutke from Shopify. We were chatting about just what is the most important things to incubate in your child? And his answer I loved, which is just, “Curiosity.”

Krithika Shankarraman: I love that.

Lenny Rachitsky: Yeah, and that’s what you’re kind of speaking to is just 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.

Krithika Shankarraman: 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?

Lenny Rachitsky: That reminds me. 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’s focus on the AI and pricing strategy. Just 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?

Krithika Shankarraman: Again, there’s no playbook. 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, but it also helped them focus up market, on higher ACV deals.

And so that trade-off is really hard to make, 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 seed-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, especially with agents coming into play. How you pay for AI workers is going to be very different. What is that unit of completion for things like code generators? It’s going to be a Wild, Wild West before we come up with something that is as internalized now as seed-based pricing or usage-based pricing.

Lenny Rachitsky: Wild indeed. I want to actually follow this insight you had around Retool. That’s really interesting. Yeah, 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.

Krithika Shankarraman: There were two guiding principles here. One is, do people actually want to talk to sales before they get a self-hosted thing? It’s sort of like the SSO attacks, right? Is that really the thing that you want to gate your value on? 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 size, you might want self-hosted. So that insight kind of led us to say, “Hey, where is the delineation here? Because the sales team should be talking to larger customers, landing larger deals.” And so to align those two was one of the driving principles.

Lenny Rachitsky: Awesome. Okay. Two final questions before we get to our very exciting lighting around. 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 or do faster work, to be more efficient. Is there something there that you could share? And if not, that’s also totally cool.

Krithika Shankarraman: Ooh, 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 I 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 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.

So I think the ability to mix AI tooling then 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 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 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 dust they could sprinkle on top of their product experience for their customers.

Lenny 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?

Krithika Shankarraman: And again, this question’s hard because there’s so many things to choose from as potential examples here. And you’re absolutely right, Lenny, in that most careers are not the sort of linear journeys that are reflected on somebody’s LinkedIn profile. No, I’ll talk about a fantastic success, which is called Stripe Relay, which you probably… Oh, I’m just kidding because nobody remembers it. 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. It didn’t produce the sort of revenue or the numbers that we had expected.

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 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? 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.

Lenny Rachitsky: This reminds me of when Kevin Weil was on the podcast talking about Libra, which was his 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 our 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 dream that would be. Okay. Krithika, is there anything else you wanted to share or maybe something you wanted to remind 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.

Krithika Shankarraman: 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 seems like there’s a playbook for everything, there is a framework for everything, but the reality is the work 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. 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 in the absence of that, nothing is going to be a substitute to bring that combination of ingredients together.

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

Krithika Shankarraman: Hit me.

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

Krithika Shankarraman: 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, 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 years has been Madeline Miller’s Circe, which is a retelling of a Greek myth. Lyrical prose, beautiful writing, highly recommend.

Lenny 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.

Krithika Shankarraman: And mine.

Lenny 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?

Krithika Shankarraman: 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.

Lenny Rachitsky: Wow, okay. It’s hard to weigh the spoilers, but yeah, keep going. It’s amazing. Do you have a favorite product you’ve recently discovered that you really love?

Krithika Shankarraman: Granola for meeting notes because, all right, 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 furiously typing away. And so the ability to augment my notes and bullet points has been a game changer.

Lenny 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 lennysnewsletter.com and click Bundle, and sign up and get Granola. So cool. I love that.

Krithika Shankarraman: Happy to help, Lenny.

Lenny 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?

Krithika Shankarraman: 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, 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.

Lenny 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 a something did and setting their expectations correctly. Final question. Okay, we’ve already talked about the em dash, but I want to ask you again. What I’m finding is, so the story here is basically people have discovered ChatGPT’s using em dashes a lot, which are these long dashes that you have to use special couple letters on the keyboard to use. I’m a huge… I use these all the time, and people are starting to filter them out on Twitter because they’re assuming it’s generated by ChatGPT. There’s content that has em dashes they assume isn’t real. Will you continue using em dashes in spite of all this?

Krithika Shankarraman: I have begrudgingly reduced my usage of em dashes-

Lenny Rachitsky: Same.

Krithika Shankarraman: … but you will not pry them out of my cold dead hands if you tried.

Lenny Rachitsky: Oh, man, me too. I don’t even know. It’s like command, options, dash or something to even put it in there.

Krithika Shankarraman: No, it’s option, shift, minus.

Lenny Rachitsky: Option, shift, minus.

Krithika Shankarraman: Yeah.

Lenny Rachitsky: I have to type it. I can’t conceptualize in my head. Yeah, and then there’s actual rules for when an em dash is the right thing versus, there’s a middle-

Krithika Shankarraman: Em dash and the Oxford comma, the two core tenets of my toolbox.

Lenny Rachitsky: Is an Oxford comma where you add the comma at the end or you don’t? Is that the-

Krithika Shankarraman: You keep the comma at the end. You must.

Lenny Rachitsky: Okay. I’m all for that, too. It looks so weird without it. But there’s also another, like a shorter not em dash. I guess it’s called something else, right? There’s like-

Krithika Shankarraman: The en dash, yeah.

Lenny Rachitsky: En dash.

Krithika Shankarraman: That’s for ranges of numbers.

Lenny 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?

Krithika Shankarraman: Krithix.com is where you’ll find links to all 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.

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

Krithika Shankarraman: Yes, please.

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

Krithika Shankarraman: Thank you for having me.

Lenny 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.

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