Lenny's Podcast: Product | Career | Growth - Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman

Starting point is 00:00:00 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. You were the first marketing hire at OpenAI. I believe ChatGPT is the fastest growing product in history. I'm asking this. A lot of people might be hearing like, oh, Chad GPT, it's like, why do you need marketing? Everyone knew of ChatGPT.

Starting point is 00:00:20 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 the sort of use case epiphany where people could say, I had no idea Chatship BT 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? If your advice is don't just copy what other companies do, what should people be doing?

Starting point is 00:00:49 Put together like a four-step process that has served me pretty well. The first step here is... Today, my guest is Krithika Shanka Raman. Krithika was the first marketing hire and VPR 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.

Starting point is 00:01:21 In our conversation, we talked through all of the biggest lessons that she has learned about how to market your product from her time. 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, have you become an annual subscriber of my newsletter. You get a year free of a bunch of world-class

Starting point is 00:02:01 products, including Superhuman, Notion, Linear, Perflexity, and Granola, and more. Check it out at Lenny's newsletter.com and click bundle. With that, I bring you Krithika Shankar Ramen. This episode is brought to you by Epo. Epo is a next generation AB testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and Drow. Raff Kings rely on Epo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features.

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Starting point is 00:04:14 Ready to see it in action, head to Airtable.com slash Lenny to book a demo. That's Airtable.com slash Lenny. Krithika, thank you so much for being here and welcome to the podcast. Thank you so much for having me. I'm excited to be chatting. 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 Open AI. 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 best.

Starting point is 00:04:59 fastest growing product in history. Does that resonate? It does, not that I can take credit for it. We'll talk about that. Either way, nice job. Let me ask you this. A lot of people might be hearing like, oh, chat GPT. It's like, why do you mean 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? You just talk about just like the value that a marketing person adds to a product like that. That's already incredible. Yeah. When you think about all of the different stages of the funnel, awareness was clearly not the problem that chat chbt or open AI had. Everyone knew of chat chit. 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

Starting point is 00:05:41 what it replaces. Like, should I be using search for this? Should I be using chat chapit for this? Or how can it even help me? And so the work of marketing ended up becoming creating the sort of use case epiphany where people could say, I had no idea chat chad chad pt could do that. And yeah, maybe I should be using it for XYZ 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. 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 like this is a thing marketing can help you with is helping people understand.

Starting point is 00:06:26 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. Yeah, 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.

Starting point is 00:06:53 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. The other element of chat GPT's marketing success, I know that you speak, spent a lot of time on the enterprise side is just like consumer-ish marketing tactics for

Starting point is 00:07:29 enterprise-y products. Can you just talk about that? And it feels like that's emerging more and more just like consumer tactics for enterprise products. 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 ChatGBTGPT Enterprise, which was one of my first launches at the company,

Starting point is 00:08:02 our lead volume 40X to 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, lead scoring model that was used in production for way too long, longer than I'd care to admit. It's so funny, I think about when Chad GPT first launched and OpenA, I just launched, everyone was just like, how will you make money?

Starting point is 00:08:31 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 saw this. He just like, at some point, we will ask chat GPT, how do we make money? 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

Starting point is 00:08:54 pricing model. And it's something that you've talked about in your newsletter and so on. But there's a value creation aspect to using AI that doesn't kind of 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. I will say, though, in terms of pricing, it feels like JETCP, it's like it works.

Starting point is 00:09:31 It's just like a monthly fee, chalk 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 old is to make money. Like now it seems so obvious. Truly was a research preview. And then they just, and I remember Sam only just launch here, check out this chat thing that we are trying with. and then just the fastest product growth in history. No big deal.

Starting point is 00:09:52 I want to come back to this point you made about this playbook, anti-playbook kind of thinking. You kind of pointed out that with chat GPT and Open AI. There was no playbook, and you find that often people following playbooks don't work. Talk about that insight. In my current role and in my career, I've spoken with a lot of founders,

Starting point is 00:10:12 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 Open AI 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'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 kind of copying the

Starting point is 00:10:46 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 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. So let's follow that thread because everyone's like, God damn, I need a play. I just tell me how to do this. Okay. So there's no playbooks that, like if your advice is don't just

Starting point is 00:11:25 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? 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

Starting point is 00:12:08 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 like, 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? 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 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 it 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.

Starting point is 00:13:07 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 differences. 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 competitor's 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

Starting point is 00:13:44 kind of give you a useful baseline. 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

Starting point is 00:14:22 cross-apply and bring in and steal into your own domain or vertical instead. And in 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 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. Let me summarize what you

Starting point is 00:15:07 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 going to, I need a hire a demand gen person or a paid growth person or a CEO person or, I don't know, content, right, 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, you'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 sounds like the core part of it is just make sure you differentiate and choose a different path

Starting point is 00:15:44 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 could work. I'm a marketer through and through now. So, I mean, you've got diagnosed D, analyze A, take a different path, T, and experiment for the E. So it's the date framework. I just coined it. Oh, beautiful. Okay, we got any framework. Cut off the presses. I love it. Date. Okay.

Starting point is 00:16:12 So with differentiation, what's your thoughts on being saying you're just a lot better or a lot cheaper? 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 same. 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're looking for something that aligns with their values, aligns with what their goals are. And so if you can be really

Starting point is 00:16:55 crisp on understanding the user need, understanding what is the problem 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. Awesome. Okay. So let's go through an example of a company you did this with. And this may take us to another company you worked at in the stories there. Yeah.

Starting point is 00:17:19 One that comes to mind is definitely Retool. Retool was very different from both my experiences at Stripe and at Open AI because both Stripe and Open AI 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 a 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

Starting point is 00:17:54 introducing ourselves to the neighborhood. So thinking about outbound channels and building demand engines was the name of the game. And here, you know, one of the first of the 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

Starting point is 00:18:37 is your impact on either signups of your 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 have 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

Starting point is 00:19:20 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 type of event formats to see what actually work best for us and scale the ones that worked and discarded the ones that did it. Okay, there's so much here. So in the

Starting point is 00:20:04 diagnosed up, I think it 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 a start expanding our top of funnel with all these different channels. And really litigate some of those channels too because on the surface they might be working, but they're actually driving pipeline and revenue.

Starting point is 00:20:38 Got it. So they may be showing like vanity metrics. Like numbers are nice at the top, but they're not sales qualified potential. They don't actually stick around. Okay. And then the analyzed competition is really interesting. So again, it's just like, what are they doing? What can we be doing differently?

Starting point is 00:20:53 Does it ever make sense just to do what they're doing but do it better? Or is that like rarely a successful path? 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,

Starting point is 00:21:13 the seller side of the marketplace. And we were really, 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 PFAC 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,

Starting point is 00:21:38 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 Pfac without actually like 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. Like here's all the things that you have to do. And by the way, if this feels onerous or annoying, it is.

Starting point is 00:22:11 And you should use Stripe Connect instead. So we're still a little bit of a zinging 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. or revenue that it drives for the company. Okay. And this is a great segue way to Stripe, which another company, you were the very first marketing

Starting point is 00:22:33 higher at. You're also, I believe, the only marketing person for three years at Stripe. I do not recommend that to anybody. 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? Oh, man, there are so many things to choose from because I was Stripe, but for almost

Starting point is 00:22:55 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. The experience really taught me the

Starting point is 00:23:36 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 did 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,

Starting point is 00:24:05 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 craftsmanship that went into the product was another lesson that I learned very deeply at Stripe. 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.

Starting point is 00:24:35 What is it that marketing most adds to a product like Stripe? 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 are head of partnerships at the time, Dina Cordova handed me a hackpad at the time, which is like a notion dot. I remember a hackpad that turned into Dropbox paper. That's right. And so she had kept a hackpad, a secret hackpad away from the engineering team, which

Starting point is 00:25:07 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 that 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 Nordstar. Engagement became the Nordstar rather than just the binary,

Starting point is 00:25:38 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 pull 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.

Starting point is 00:26:22 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? 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? 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.

Starting point is 00:27:06 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 teaching, people who could be. flexible to those needs of the company. Coming back to your point about how there's no playbooks, is that a 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. Yeah, if we did, we would still be talking about PCI compliance and payment gateways. There's so much of what you share that reminds me of Roz from WIS,

Starting point is 00:27:44 who also, you were an engineer originally. She was a product person. Yeah, I think, I don't know if he was an engineer, but a product person. And so it's your – Their first PM, actually. Yeah, RAS is great. Okay. And it's – I think there's a few things that are so interesting here.

Starting point is 00:27:57 One is you both have like non-marketing backgrounds. Like you went from up another function. And I think it – you tell me, it gives you like a whole new perspective on marketing, not just like the traditional education of marketing. Is there anything there? 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?

Starting point is 00:28:19 like 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. And 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. 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 cloud security, but it's just like, we don't, we're not this thing.

Starting point is 00:28:51 We're whiz. Here's what we do. They are definitely a company that Zags win others. I still have my Wiz socks, which have these beautiful eight-bit characters on them. Their branding really stands out in the sea of sameness in SaaS conferences. 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 the biggest customer support issues and you

Starting point is 00:29:15 turn those into docs to help people serve themselves. Can you just talk about that insight and the power of doing something like that? 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, like, these are the areas that people are confused about. Again, I kind of mentioned the sort

Starting point is 00:29:55 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. 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

Starting point is 00:30:34 that we produced that just educated people. And this is really important when you have strong top a funnel of 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 a great way and a great program to figure out what content we should focus on Prioritux. These are really cool. Just little ways as a new marketing person you can add value really quickly

Starting point is 00:31:19 is kind of what I'm taking away. Talking to customers is at the top of the list. 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 one billion professionals, including 130 million decision makers. And that's where it stands apart from other ad platforms. You can target your ad buyers

Starting point is 00:32:02 by job title, industry, company, role, seniority, skills, even company revenue, all the professionals 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 slash podlennie. That's LinkedIn.com slash pod lenny. 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.

Starting point is 00:32:41 Like, let's just move fast. We don't need to like have all these meetings or people review stuff. But I know you're a big advocate of that. Talk about why that's so important. 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 process. 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

Starting point is 00:33:11 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 hypergrowth 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.

Starting point is 00:33:54 I understand the unspoken rules of the organization. I've built up enough social capital that I can withdraw from to get something done. 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. 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.

Starting point is 00:34:32 great looks like at the company. Can you speak more about what this looks like, say a startup wants to start implementing something like this? Two simple processes that you could put into place today is one set up a forum called marketing review. This can be an 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 organizations. 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?

Starting point is 00:35:11 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 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. 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

Starting point is 00:36:17 organization learn from each other. 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 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.

Starting point is 00:36:40 Just like, why is that important? Why do you value that? Why should companies maybe value that more? 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.

Starting point is 00:37:08 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?

Starting point is 00:37:39 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. 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

Starting point is 00:38:14 an email by accident to everyone that's not ready. I just feel like once I break that, 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.

Starting point is 00:38:34 And so it's just like a constant fear I have now of breaking that trust. Yeah, I mean, whether 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.

Starting point is 00:38:57 And to what you said, if you have a strong brand that people trust, everything gets easier. You pitch them on a new product, oh, I'm going to 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 opening AI launch or something, you know. So it just makes life easier if your brand is strong, if there's trust. 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 opening eye. When we launched something, even though we were trying to be

Starting point is 00:39:34 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. Let's actually come back to OpenAI. How long were they around until before you joined? It was like many, many years, right? Many, many years. So Open AI had been around for almost a decade. As primarily a research organization, they had launched Chat GPT about a year before I joined. And so that was the first foray into saying, hey, our work is not just announcing research breakthroughs.

Starting point is 00:40:15 It is about putting products into the market. So there's a few questions I'm asking here. When is it time to bring in Acrithica? 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, I think we need a marketing person that knows what they're doing. I think the first criteria is having tremendous product market fit, which is really important because you're throwing fuel on the fire.

Starting point is 00:40:39 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, 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

Starting point is 00:41:09 engagement. Differencesation 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 and 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

Starting point is 00:41:34 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 And this is an important distinction I've learned over the years, which is capital M marketing, the marketing team, the marketing function of 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 like the discipline of marketing. And that's where the lower case M marketing comes in, which is, what do you stand for as a

Starting point is 00:42:13 company? 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. And then it is this entire joining of the organizations to make that happen really effectively. Yeah, I think along these lines, there's a reason and Brian at Airbnb merged marketing and product marketing and product management, however much

Starting point is 00:42:55 that actually happened or not. But the intent is. I would be so curious to see a follow-up a few years on on how that's been going. Yeah, that's okay. Let's have Brian back to talk about that. That'd be really interesting. I want to actually ask, so an interesting thing is happening with JATGPT versus Claude. And 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 about a writer in a lot of ways. People prefer it for writing. But it's just like chat chitp t is just dominating.

Starting point is 00:43:27 It's like, that's what people associate with AI now is just chat chitp t. It's just like caught mind share globally. What is it do you think that allowed chaty pt just to be that? Is it just first move for advantage? Is it some kind of other element? Is it just been better, longer? Like something really interesting is going on there. 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.

Starting point is 00:44:00 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 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 delight. 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.

Starting point is 00:44:36 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

Starting point is 00:45:22 competition and one-upmanship, but rather thinking about the paradigm changes that need to happen for our society writ large. 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 there seem to be at the this 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 are, what's like something people may not know that's a like a wonderful positive element of how open AI works? That's just like, oh, that's super interesting. And then what's what was maybe a challenge of working at open AI?

Starting point is 00:46:08 A surprising thing that surprised me at the company was just the warm than 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,

Starting point is 00:46:33 the rigor with which products were developed, go-to-market strategies were developed, was Barnett. And so that's something that I really admire. 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 Open AI at all times.

Starting point is 00:46:55 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. 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?

Starting point is 00:47:25 I'm a big believer of what Claire Hughes-Johnson, who a CEO 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

Starting point is 00:47:49 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 something, you know, 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 the third is sort of potential, right?

Starting point is 00:48:16 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. 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.

Starting point is 00:48:52 So share what you do there. And then what are some things you've learned there so far from our perspective of marketing? Yeah, surprisingly, more people know about Thrive these days than used to even just a few years ago. And that'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.

Starting point is 00:49:32 Yeah, Thriye'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.

Starting point is 00:50:06 Sometimes it means looking at a Figma file for a landing page that's going out the next. 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 data bricks and stripe and open AI when it comes to the types of organizations that we work with. And then 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. And so what are some things you've learned so far?

Starting point is 00:50:46 Because I imagine this is a very different experience that I don't know, especially things that you've like changed your mind on even working with a bunch of companies early stage versus. It's a really different method of operating. And so when you're in the leadership role for marketing within a single organization, 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

Starting point is 00:51:21 with Open AI and Stripe, but it can span B to C, B to B to 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. 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

Starting point is 00:52:08 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 and going into uncharted territory alongside these founders. I bet they're all like, Krithica, what is the playbook for growing this BW SaaS company? And you're like, no. And I say there is none. 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. 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

Starting point is 00:53:07 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 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.

Starting point is 00:53:53 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. That sounds very hard. I love this metaphysical of the cope shape. It sounds like I have so much to learn, so many little skills to build. This is where AI can come in handy. Some of the most like brand marketers can become very analytical with the support of a tool like chat chip. If your eyes glaze over when you look at giant dumps of CSVs, it's nice to have a partner that is non-judgmental 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 Chad GPD to be more of a brainstorm partner and really push your thinking on the creative side.

Starting point is 00:54:53 So I think becoming a non-just T-shaped marketer is getting a little bit easier. That's such a good point. It gets like way to an AI question. We've got to talk about AI. One of your former colleagues, Kevin Garcia, wanted me to ask you something. He suggested to 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.

Starting point is 00:55:19 You do pottery shirt. 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. I think it's going to become so much more important. First of all, I will say I am not a chat GPT-hyphen person. Like I was an M-Dasher well before it became a chat-G-T. Me too. I hate that, but just for people don't know, like people are filtering out M-Dashes, right?

Starting point is 00:55:46 Because I think chat-GPT is the only thing using their dashes. I don't know what to do about it because this is such a core part of my identity. But 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, or 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,

Starting point is 00:56:23 and connect the two in meaningful ways. If they can use AI to augment their efforts to make that happen, that's better than subsuming their efforts. So to build taste, you know, there's plenty of past episodes that you yourself have recorded that get into building that work. But to mean, that is going to be a real differentiator for not only great marketers, but great companies to stand out in the field. There's a concept that I love that recently I learned from Guillermo at Vursell.

Starting point is 00:56:55 He calls it exposure hours. as a, that's when I asked them 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. Yeah. At Thrive, we have this share channel, which is just sharing things that we're seeing out into

Starting point is 00:57:14 the world. It's not particularly deal flow news or competitive news or anything like that, but it's things that we have seen that resonated with us for whatever reason. Along these lines of not overlying on chat, GBT, 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 never learn 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.

Starting point is 00:57:42 I guess, do you have any advice for folks that are early career, just like how to find that balance of not over relying, but still leveraging these tools? 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,

Starting point is 00:58:23 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 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.

Starting point is 00:58:46 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 I'll, this time. I'll just ask Chad Shabitia, help me with this one. 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,

Starting point is 00:59:11 it's a very different mindset than if you go to school to learn those concepts and to understand how to apply that. That's something that stuck with me for my chat with Toby Luckke 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 curiosity. I love that. Yeah. And that's what you're kind of speaking to is just like if you're curious about learning,

Starting point is 00:59:37 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. And that stays with you into your career, right? Because you can either go into your career or 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? That reminds me. I wanted to come back to sort of close out our conversation. I want to come back to pricing strategy. I have that in my notes here,

Starting point is 01:00:10 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 use? 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

Starting point is 01:00:52 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 upmarket on higher ACV deals. And so that tradeoff is 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 seed-based model? Is that where people are deriving value? Or is the way that they speak about the value of the product something

Starting point is 01:01:34 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 on. off of it. And I don't think anyone solved it. Like there's, especially with agents coming into the, to play, 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 seed-based pricing or usage-based pricing. Wild indeed. I want to actually follow this insight you had at a retool. That's really interesting. So you had what was, so you opened up self-hosted retool. What was the insight there?

Starting point is 01:02:22 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. 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? Like is that really the thing that you want to gate 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

Starting point is 01:03:04 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 sales team should be talking to larger customers, land, larger deals. And so to align those two was one of the driving principles. Awesome. Okay. Two final questions before we get to a very exciting lighting around. I'm going to take you to a couple recurring segments on this podcast. The first is AI Corner. And with AI Corner, what I try to get to 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.

Starting point is 01:03:46 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 process. 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

Starting point is 01:04:22 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 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 Google Group's archives or talking to people across the organization to pull out things that are inside of their brain, that kind of institutional knowledge

Starting point is 01:04:53 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.

Starting point is 01:05:15 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 into the right

Starting point is 01:05:36 and always win, win, win. Is there a story from your career you can share where things didn't work out? what you learned from that experience. 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 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 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,

Starting point is 01:06:16 you know, 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. 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,

Starting point is 01:06:51 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 system? 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. This reminds me of when Kevin Wheel was on the podcast talking about Libra, which was this

Starting point is 01:07:26 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. for them to send money internationally for free. What a dream that would be. Okay, Carithica, 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 a very exciting lightning round? 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

Starting point is 01:08:04 playbook for everything. There's 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, like what are you bringing to the table, and not just your product, but your company's values,

Starting point is 01:08:29 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. With that, we've reached our very exciting lightning round. We have five questions for you. Are you ready? Hit me.

Starting point is 01:08:52 Here we go. What are two or three books that you find yourself recommending most to other people? 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.

Starting point is 01:09:19 So I would say one of the best reads in the last couple of years has been Madeline Miller's Circe, which is a retelling of a Greek myth. So lyrical prose, beautiful writing, highly recommend. 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. And mine. 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? 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. 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?

Starting point is 01:10:03 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. That's two guests in a row that said granola. And I'll give a plug. You get a year free of granola to become an annual subscriber of my newsletter for not just you,

Starting point is 01:10:29 but your whole company up to some limit. check out Lenny's newsletter.com and click bundle and sign up and get in granola. So cool. Happy to help Lenny. 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? 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.

Starting point is 01:11:02 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 tradeoffs that we're making or why we're making certain decisions. So I could not espouse that philosophy enough. I love that this isn't, because I think when people fear for hear that, it's about your own happiness, but I love that it's about other people perceiving how

Starting point is 01:11:34 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 GPTs using M-dashes a lot, which are like these long dashes. They have to use like special couple 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 because they're assuming it's generated by chat GPT, there's like content that has

Starting point is 01:12:01 m dashes they assume isn't real. Will you continue using m dashes in spite of all this? I have begrudgingly reduced my usage of m dashes, but you will not pry them out of my cold dead hands if you if you tried. 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. No, it's it's option shift minus. Option shift. 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- The M-Dash in the Oxford comma, the two core tenets of my toolbox. Is it an Oxford comma where you add the comma at the end or you don't?

Starting point is 01:12:39 You keep the comma at the end. You keep, okay, 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? N-M-Dash, yeah, that's for ranges of numbers. Okay, okay, I love that you know all this. Okay, well, with that, Krithica, 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

Starting point is 01:13:00 to reach out, maybe work with you? And how can listeners be useful to you? Critics.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. And then what's the best wait for them to reach out to you. Is it just on your website? Yes, please. Amazing. We'll link to that. In the show notes, Krithika, thank you so much for being here. Thank you for having me. 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.

Starting point is 01:13:45 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 Lenny'spodcast.com. See you in the next episode.

Lenny's Podcast: Product | Career | Growth - Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman

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