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

It seems like there's a playbook for everything. There's a framework for

everything. There's a framework for everything. But the reality is you have

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 chat GPT is the fastest growing product in history. Let me ask you this. A lot of people might be

you this. A lot of people might be hearing like oh chat GPT. It's like why do you need marketing? Everyone knew of chat GPT. But when you clicked one Zoom

chat GPT. 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 catchup 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

impressions. I think those are all numbers. What is that

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? Put together

like a four-step process that has served me pretty well. The first step here is today my guest is Critica Shanka Ramen.

Critica 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 3 years.

She was also an early marketing leader at Retool and at Dropbox. She also did marketing for Android at Google.

Currently, she's 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

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With that, I bring you Critica Shanker Ramen. This episode is brought to you by

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Corithica, 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 uh leading marketing at these companies. And I want to start with

companies. And I want to start with OpenAI. No big deal. You were the first

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?

It it does. Not that I can take credit for it. We'll we'll talk about that. Uh

for it. We'll we'll talk about that. Uh

either way, nice job. Let me ask you this. A lot of people might be hearing

this. A lot of people might be hearing like, "Oh, Chad GPT, it's like like why do you need marketing? It's like the most magical thing in the history of the world." Like how much value does

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 chatbt or OpenAI had.

Everyone knew of Chat GBT. But when you clicked one zoom level further, the thing that came up was I don't know what to use it for. Like I don't know what it replaces. Like should I be using search

replaces. Like should I be using search for this? Should I be using chatbt for

for this? Should I be using chatbt for this? Or you how can it even help me?

this? Or you 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 chatt 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, they don't a lot of them don't have a lot of experience with marketing. I think it's an important insight there of just like

this is a thing marketing can help you with is helping people understand how to use your product, understand use cases understand examples, things like that.

So I think as we go through this, I think this is useful for folks to understand of like here's what you may not be good at and may need marketing help with. Yeah. When done right

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

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 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

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 lock step with the product management side. The other uh element of

management side. The other uh element of Chad GBT's marketing success. I know

that you spent a lot of time on the enterprise side is just like consumerish marketing tactics for enterprise products. Can you just talk

enterprise products. Can you just talk about that and 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 ChatGpt Enterprise, which was one of my first

launches at the company, our lead volume 40xed overnight. It was unanticipated

40xed overnight. It was unanticipated even beyond our wildest expectations.

And so some of the things that I had to do are not typical to marketing at all.

Like I sat down with ChachiBT 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 OpenAI just launched everyone was just like, how will you make money? How do you make money with

make money? How do you make money with something like this chatbot that's pretty interest like smart but sort of not that smart? I remember there's a video of Sam Alman being asked, "How do you make money with something like this?" and he's I don't know if you just

this?" and he's I don't know if you just saw this he just like at some point we will ask JGBT 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 pricing model and it's something that you've talked about in your newsletter and and so on but

there's a a value creation aspect to using AI that doesn't kind of neatly fit the mold of SASbased pricing or seatbased pricing or even usage based pricing. So I think there are still some

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

maximize. I will say though in terms of pricing, it feels like JB it's like a like it works. It's just like a monthly fee. Talk to it up to a certain limit.

fee. Talk to it up to a certain limit.

Uh it's wild to think back now there was a sense we will we don't have no idea how this make money like now it seems so obvious truly was a research preview and then they just and I remember Sam

Alman just launched here check out this chat thing that we are trying with and then it just the fastest product growth in history no big deal I want to come back to this point you made about this playbook anti-playbook kind of a

thinking you you kind of pointed out that with chat GPT and open AI there was there was no playbook and you find that often people following playbooks don't

work. Talk about that insight. In my

work. Talk about that insight. In my

current role and in my career, I've spoken with a lot of founders and typically the founders reach out because I've worked at companies that they look up to and they're looking for that playbook. They're looking for, hey, just

playbook. They're looking for, hey, just like tell me how Stripe did it. Tell me

how retool did it. Tell me how open AAI did it. And I really hesitate to share

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 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 just tell me how to do this. Uh, okay.

So, if there's no playbooks that like 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?

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 like a four-step process that has served me pretty well. The 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 genen leader. Like who do you know in your

leader. Like who do you know in your network that we should be thinking about? And I'm like, let's talk about

about? And I'm like, let's talk about your funnel. Do you have a lot of people

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? Like once you're already in the room and people are converting, you have found that problem statement that is uh critical to them

that is hurting them the most and your solution is resonating as uh a as a solve to that problem. And so that means yes, probably

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

that time. But on the other hand, if you say, "Yeah, I mean, like we get a lot of interest, but once they're in the room they have a bunch of questions. They're

asking about, you know, how do you compare to X competitor and Y competitor and why does it cost so much and etc etc., 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 like analyzing your

top. Second to me is like analyzing your competitor's approaches. So to me, this

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

company. But when you analyze your competitor's 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

is doing. And so driving a strategy that sort of sets the company apart is really critically important. I think it's so

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

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

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.

Like that 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

marketing. So experiment, test validate, give people that psychological safety to fail, especially your teams and organizations. And then yeah, once

and organizations. And then yeah, once you find what works, really double down on it. Let me summarize what you just

on it. Let me summarize what you just shared here. So essentially, if you uh

shared here. So essentially, if you uh think you're like, I need help with marketing or I have a problem and I think I'm going to I need to hire a demand genen person or a paid growth person or SEO person or uh I don't know

content, right? Or something like that.

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

diagnose. Spend time understanding what's the specific problem you want to solve. Then analyze. This is this is so

solve. Then analyze. This is this is so interesting. I've never heard it this

interesting. I've never heard it this way. So then it's analyze what your

way. So then it's analyze what your competition is doing so that you can then one find opport like uh inspiration and see where gaps exist and then sounds like the core part of it is just make

sure you differentiate and choose a different path versus just try to be the better thing or the cheaper thing and then the final piece is just like okay here's our path let's test run some

small scale test 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 the date framework. I just coined it. Beautiful. Okay, we got a new

it. Beautiful. Okay, we got a new framework. Hot off the

framework. Hot off the presses. I love it. Date. Okay, with um

presses. I love it. Date. Okay, with um 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 um 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

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 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

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 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 let's go through an example of of a company you did this with and this may take us to another company you worked at and the stories there. Yeah, one that comes to mind is

there. Yeah, one that comes to mind is definitely Retool. Retool was very

definitely Retool. Retool was very different from both my experiences at Stripe and at OpenAI because both Stripe and OpenAI for better or for worse were inbound companies, right? There was so

much latent demand that we were fighting off people breaking down the door trying to get to our products. With Retool

marketing was between the company and revenue and we had fantastic product market fit with the enterprise space with the developer community, but awareness was a challenge. And so, how

do we go out not just like wait inside of our house waiting for people to knock down the door, but rather step outside of our house and start introducing ourselves to the neighborhood? So

thinking about outbound channels and building demand engines was the name of the game. And here, you know, one of the

the game. And here, you know, one of the ways to think about that is, hey, should we just scale the paid marketing channels that we already have working for us? And that's when the diagnostic

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

funnel? Are they turning into salesqualified opportunities? What kind

salesqualified 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 a tweet got, number of impressions. I think those are all

impressions. I think those are all numbers. Like really what you

numbers. Like really what you want to be looking at is your impact on either signups if you're a self-s served product PLG or in in terms of a B2B

company sales leads and revenue that you're driving pipeline and opportunity that you're driving. So we diagnosed that and we found that for the most part our paid social channels were doing not

much for us and so we had to invest in new engines. So that was that

new engines. So that was that diagnostic. When we looked at some of

diagnostic. When we looked at some of the competitors, you know, we saw that they were doing a lot of content marketing, they were doing a lot of events programming and like we could have kind of followed in those

footsteps, but there was the ability to take a different path. And so what we decided to do was double down on customer marketing and customer storytelling because the thing that

differentiated Retool from a lot of the copycat competitors in the market was that we had terrific traction with true 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

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

possible. And then we experimented. We

tried to put together webinars different types of sales dinners different type of event formats to see what actually worked best for us and scaled the ones that worked and and discarded the ones that didn't. Okay

there's so much here. So in the diagnose step, I think a kind of a uh 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 and really litigate some of those channels too because on the surface they might be working but

they're actually driving pipeline and revenue. Got it. So they may be showing

revenue. Got it. So they may be showing like vanity metrics top like numbers are nice at the top but they're not salesqualified potential. They don't

salesqualified potential. They don't actually stick around. Okay. And then

the analyze competition is really interesting. So again it's just like

interesting. So again it's just like what are they doing? What what can we be doing differently? Does it ever make

doing differently? Does it ever make sense just to do what they're doing? do

it better or is that like rarely a successful path? You still have to do

successful path? You still have to do something a little bit different. I

recall a very specific example at Stripe where uh you know our 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 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 payac yourself. And a lot of the

payac yourself. And a lot of the services organizations, the consulting groups that were helping companies become pays, 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 payac without actually like talking about ourselves as a payac 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 ownorous 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. Okay

that's a great segue to Stripe, which uh uh another company you were the very first marketing hire at. You were also I believe, the only marketing person for three years at Stripe. I do not

recommend that to anybody.

There's the lesson there. Uh okay, so let's talk about Stripe. What are some of the 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

founders? Oh man, there are so many things to choose from because I was Stripe for almost 8 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

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 importance of deep product understanding as well. Like you couldn't really play

as well. Like you couldn't really play act at understanding the product especially when developers are trained to spot bugs, right? So not only do they spot those bugs in code, they spot those

bugs in marketing and in blog posts. And

so if the marketing pieces are your first impression of the product, they are an extension of the product itself.

You have to hold yourself to a very high bar in terms of how you communicate about the product. And so we did a lot of investment in design work in polish in terms of how the marketing came

together and you know 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 I learned very deeply at Stripe. So

kind of along those lines uh 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

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? Across my time at Stripe

Stripe? Across my time at Stripe marketing are very different purposes.

And so I kind of see it in different epochs or or chapters of my time at the company. The first chapter when I

company. The first chapter when I joined, our head of partnerships at the time, Christina Cordova, handed me a an a hackpad at the time, which is like a a

notion. I remember Hackpad that turned

notion. I remember 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 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 northstar.

it." So usage became the northstar.

Engagement became the northstar rather than just the binary has it launched or not. The second chapter at Stripe was

not. The second chapter at Stripe was really starting to expand what a launch meant, right? So going from just putting

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 you know developer experience

as a function you built out developer relations to really have that that community feeling and vibe. And then it was about starting to think through the multi-product ecosystem. So Stripe went

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.

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

and especially in hyperrowth companies I think you have to run that diagnostic every 3 months every 6 months in order to stay adaptable and flexible because those top level goals do change you know at some point we really had to figure

out how to scale our sales function we had to figure out how to scale internationally and so being adaptable to that meant um constant rep prioritization 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. Coming back

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

would still be talking about PCI compliance and payment gateways. M uh

there's so much of what you share that reminds me of Ros from Whiz who also you were an engineer originally. She was a product person. Yeah. I think I don't

product person. Yeah. I think I don't know if she was an engineer but a product person. So it's your first PM

product person. So it's your first PM actually. Yeah. Raz is great. Okay. And

actually. Yeah. Raz is great. Okay. And

it's I think there's a few things that are so interesting here. One is you both have like non-marketing backgrounds like you went from another function and I think it you tell me it gives you like a whole new perspective on marketing not

just like the traditional education of marketing. Is there is there anything

marketing. Is there is there anything there? One thing that's definitely made

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?

Like what developer is clicking on paid ads? Isn't a better thing that we could

ads? Isn't a better thing that we could be doing for them telling them to install ad block? And so uh 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 correl here is uh she was very big on like avoiding the generic acronyms and like classic industry norms. I forget what they were for like cloud security, but it's just like we don't we're not this thing.

We're whiz here's what we do. They are

definitely a company that that zags when others zigg. I still have my whiz socks

others zigg. I still have my whiz socks which have these beautiful eight-bit characters on them. their branding

really stands out in the sea of sameness in SAS conferences. Okay. There's uh

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

themselves. Can you just talk about that insight and the power of doing something like that? Yeah, this was a great

like that? Yeah, this was a great practice that existed at Stripe even before I joined, which is all new hires would do a support rotation just to build empathy with our customers. So

users first was a very core operating principle for the company and we spent about 20% of our time collectively talking to customers, talking to users talking to non-users to understand their

needs, their gripes about the 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

confused about. Again, I kind of mentioned the sort of cheat code of talking to your customers and using the language that they use to describe their problems as a shortcut to fantastic

product marketing and messaging because it it really tells you what are their pain points and how can you meet them where they are. You want them nodding their heads along as they're reading your landing pages. And so when I was

doing the support rotation, there were thematic things that kept coming up. You

know, people were asking, "Hey, do you process subscription payments or recurring payments or can I pay people out with Stripe?" And I was like "Of course you could, but there's no reason you should know that because we don't

tell you anywhere." And so that ended up being a stacked rank backlog of landing pages that we produced that just educated people. And this is really

educated people. And this is really important when you have strong top offunnel 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

sales. It often never looks like talking to sales. It looks like a self-directed

to sales. It looks like a self-directed educational experience. Even the sales

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 and prioritize. These are really cool uh

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

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ads. There's something else that I know that you're a big advocate of, which is uh 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 like 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.

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 touch point

your product. It's the first touch point your customers have with your product.

And ideally, you're setting expectations there in terms of what they should expect once they sign up for the product or commit to a contract and start using uh it within their companies. And when I

think about that, consistency is really really important. The other part, the

really important. The other part, the other facet of why process is important is because especially as you're in hyperrowth companies, scaling teams is part and parcel like what you're trying

to do. And when you bring in someone

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

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, 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

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

powerful. Nobody wants to do the wrong thing. They want the guardrails to

thing. They want the guardrails to understand what great looks like at the company. Can you speak more about what

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 organization. So anyone in the

the organization. So anyone in the marketing team, anyone in the product organization can join that forum. What

that does is it creates a fishbowl where you see sort of what are the themes that come out when somebody reviews a piece of content. Is it are they looking at

of content. Is it are they looking at the strategy? Are they looking at the

the strategy? Are they looking at the audience? Are they looking at the words?

audience? Are they looking at the words?

Are they looking at the sort of design approach? So you learn through osmosis

approach? So you learn through osmosis of looking at at some of these discussions and then I would say don't overdo it. I would say there are

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

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

to accomplish? Who are we trying to do it for? And what is the rough approach

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 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

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

audience. and two, it helps the rest of the 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 the need and value of having consistent and high quality marketing

communication. Why is that important?

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

be scrappy. We're not going to be obsessed with like perfect quality of our I don't know websites and emails.

Just like why is that important? Why do

you value that? Why should companies maybe value that more? It's funny

because the companies who value velocity actually do value their brand just as much. But often times they think

of these as two siloed separate initiatives that they have to put their head space and calories towards. And I

actually think they are not mutually exclusive. They are actually very

exclusive. They are actually very interconnected. And so when you

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 at 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 uh very viscerally learned the power of brand doing my

newsletter. Like I so fear doing

newsletter. Like I so fear doing something very wrong in my newsletter.

It's like saying something that's completely off or having something broken or sending an email by accident to everyone that's not ready. Like I

just feel like once I break that just there's so much power and trust that people have built for what I share and there's so much power that comes from that trust. like if I launch a new

that trust. like if I launch a new podcast, you know, people will assume it will be good if they trust what I do and I maintain high quality. And so it's

just like a constant fear I have now of hurting of breaking that trust. Yeah. I

mean whether it's uh it's fear that drives you is questionable because I think it's also a commitment to your craft. But I think

that's exactly right. Like a brand is an expectation that you create within your audience. And and to what what you said

audience. And and to what what you said if you have a strong brand that people trust, everything gets easier. You pitch

them a new product. Oh, I'm I'll check like if Stripe's like, "Oh, we have a new billing service. Oh, I bet it'll be awesome because it's Stripe." Or if OpenAI launches something, you know? So

that's it. Just makes life easier if your brand is strong, if there's trust.

Yeah. and 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

people's expectations. And same thing with OpenAI. When we launch something

with OpenAI. When we launch something even though we were trying to be first to market and that velocity was so important for the company, often times 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

experience? How can we make sure that it is safe? So there were different

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

experience. Let's actually come back to open AAI. How long were they around

open AAI. How long were they around until before you joined? It was like many many years, right? Many many years.

So OpenAI had been around for almost a decade as primarily a research organization. They had launched chat GPT

organization. They had launched chat GPT about a year before I joined. And so

that was the first foray into saying hey our our work is not just announcing research breakthroughs it is about putting products into the market. So

there's a few questions I ask here. One

is just like when is it time to bring in a critica? Like when is it like okay we

a critica? Like when is it like okay we need help here or like a bunch of smart people doing great work. People love the product but like I think we need a marketing person that knows what they're doing. I think the first criteria is

doing. I think the first criteria is having tremendous product market fit which is really important because you're throwing fuel on the fire and you might be throwing different types of fuel on on your particular fire. So one pillar

for marketing that you have to think about is product marketing. So if you have a high velocity engineering organization and product organization that is putting out a lot of different features and your customers aren't able

to keep track, maybe the engagement's not so high for some of the newer features versus some of the core features that you had in the past. A

product marketer can really help bring a discipline of launch excellence and uh customer engagement, differentiation in the market. How are you positioning the

the market. How are you positioning the product? The second pillar for me is

product? The second pillar for me is demand generation. So if you have much

demand generation. So if you have much more of a salesdriven buyer journey in motion, how are you bringing the demand engines to bear so that your lead generation, your pipeline generation is

staying really strong and solid? Or you

might want to think about brand, right?

Like you might want to think about community development as a big part of what you're doing as a company. So it

really depends, but I think in all of these you found a spark of product market fit before you're really going for it. The second for me is that you're

for it. The second for me is that you're distinguishing enough between capital M marketing and lowercase M marketing. And

this is an important distinction I've learned over the years, which is capital M marketing, the marketing team, the marketing function at the company is responsible for those channels and

artifacts and engines that are driving the funnel for the company, but they are not the end- all beall of like the discipline of marketing. And that's

where the the lowercase M marketing comes in, which is what do you stand for as a company? Uh what what is the storyline that you're telling as a founder when you're talking to the press

to the the larger business community?

And then you know it really is a whole company motion where the product team is thinking about how are we going to market what are we going to market with the sales team is figuring out what is

the right ICP the right customer profile that decision makers are um that we need to be reaching and then it is this

entire joining of the organizations to make that h really effectively there.

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

been going. Yeah, that's okay. Let's

have Brian back to talk about that.

That'd be really interesting. I wanted

actually to ask so an interesting thing is happening with JGBT versus Claude.

And if like it's so interesting, Claude is arguably better at many things at code at least at this point. You know

things are always changing. People it

seems to be a better writer in a lot of ways. People prefer it for writing, but

ways. People prefer it for writing, but it's just like chat GPT is just dominating. It's like that's what people

dominating. It's like that's what people associate with AI now is just chat GBT.

It's just like caught my mind share globally. What is it do you think that

globally. What is it do you think that allowed chatbt just to be that? Is it

just first mover advantage? Is it some kind of other element? Is it just has 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.

And so every single week there's a new breakthrough in AI that comes out from some lab or the other. there's this

oneupmanship on, you know, point changes and eval numbers and and so on and so forth. But I think to to customers, the

forth. But I think to to customers, the users of the product, the things that make it delightful are the same things that make any product delightful. And uh

there's there's a sense of loyalty that builds up over time when there is a shorter and and smaller delta between your expectations and your reality. And

where those expectations are exceeded you it is accretive to the brand and your loyalty to the product. And where

there is a 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

work lives. And so to make that transformation happen, my hope is these companies are not super focused on just their competition and and oneupmanship but rather thinking about the paradigm

changes that need to happen for our society at large. It does feel like they are taking that responsibility really seriously, but it is a massive

responsibility. Before we leave

responsibility. Before we leave OpenAI, I like it feels like it may be the most impactful important company in the world right now just because they're seem to be at the furthest edge of where

AI is going. And so it's just such an interesting place to study. So let me ask you this just like as a person working there, what are what's like

something people may not know that's a like a wonderful positive element of how OpenAI works that's just like oh that's super interesting. And then what's what

super interesting. And then what's what was maybe a challenge of working at OpenAI? A surprising thing that

OpenAI? 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

service. It was something that was embodied dayto-day. the sort of

embodied dayto-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 Barna and and so that's

something that I really admire and it was a privilege to be a part of that organization. I think challenging of

organization. I think challenging of course is just being at the eye of the storm, right? The eye of the eye of the

storm, right? The eye of the eye of the hurricane. And so all eyes are on OpenAI

hurricane. And so all eyes are on OpenAI at all times. And I I think that is a 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 uh looked at with. Do you recommend that sort of uh

with. Do you recommend that sort of uh experience for people? Because uh I imagine work life balance wasn't great.

I imagine there was a lot of stress and worry constantly. uh who's like the

worry constantly. uh who's like the right person like when in your career is this a a sort of gig to take on versus not. I'm a big believer of what um Clare

not. I'm a big believer of what um Clare Hughes Johnson who was CEO at Stripe used to share with us which is there is a concept of a work life blend and and sort of making sure that you're working

at a company that has three components.

I I think first and foremost is always people. So, are the people that you're

people. So, are the people that you're surrounding yourself with ones that push your thinking, who are kind, who are genuinely interesting people to spend

your hours with because you're spending a vast majority of your time with them.

The second to me is product, right?

Like, do you go to sleep thinking about the product, waking up wanting to put it into the hands of more people because you know it is going to be good for them or useful to them. that something you

know I I'm not one of those marketers who can pick up any product and market it. I have to have that conviction

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 do 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 uh shift to talking about thrive which is where you work now and I talk about what your role is and what's interesting I think about this role is you get to work now with a bunch of different startups instead of go really

deep with one. So share what you do there and then what are some things you've learned there so far uh from a perspective of marketing. Yeah

surprisingly more people know about Thrive these days than used to even just a few years ago. And Thrive is a very unique type of investment company. And

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. You know, 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

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 uh 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 yeah the the variety of domains can range from consumer to healthcare to defense to B2B SAS to AI. So it is a

variety pack in the best way possible.

And so what are the what are some things you've learned so far because I imagine this is a very different experience uh that I don't know especially things you've like like changed your mind on

even uh working with a bunch of companies early stage versus it's a really different me method of operating um and so when you're in the leadership

role for marketing within a single organization you have at least a medium-term northstar 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. Uh that hasn't always been the

journey. Uh that hasn't always been the case, especially with OpenAI and Stripe but and it can span B to C, B2B, 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-minut call to 30 minute call. You have to go deep to

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 the reason that they want to work with Thrive is not because we are bringing our past experiences to the table, but rather because they're trying to do something new that has never been

done in the world. And so those are the engagements that are the most exciting is that you're building and going into uncharted territory alongside these founders. I bet they're all like

founders. I bet they're all like critica, what is the playbook for growing this B2B SAS company? And you're

like, no. And I say there is none. Damn.

But we got we got the framework that we talked about. Okay. I want to zoom out a

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 uh 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 t like a T-shaped marketer. And uh

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

brand marketing. And that kind of becomes your calling card in the world.

Like if a company needs brand expertise they go for this kind of flavor of CMO.

Or if a company needs to really grow their pipeline or their demand gen or their consumer growth, they go for more of like a demand and growth oriented

CMO. And I think this chameleon CMO

CMO. And I think this chameleon CMO concept is is a bit of a novel one in that again I think modern marketing leaders have to be really good at a

bunch of different things. They have to be very analytical. 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

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. That sounds very hard. I I

love this meta visual 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. You know

some of the most like brand marketers can become very analytical with the support of a tool like chatbt. If your eyes glaze over when you

chatbt. If your eyes glaze over when you look at giant dumps of CSVs, it's 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, you know, 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 chatbt to be more of a brainstorm partner and really push your thinking on

the creative side. So I think becoming a non-Just T-shaped marketer is getting a little bit easier. That's such a good point. A good segue to an AI question.

point. A good segue to an AI question.

We got to talk about AI. One of your former colleagues, Kevin Garcia, wanted me to ask you something. He suggested I ask you about taste and creativity in AI. So he said that you're one of the

AI. So he said that you're one of the best writers that he's ever worked with.

You combine technical background with creative taste. You do pottery shirt and

creative taste. You do pottery shirt and you're 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. I think

it's going to become so much more important. First of all, I will say I am

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 GP. Me too. I hate that that just for

GP. Me too. I hate that that just for people don't know talk like people are filtering out M dashes right because I think JGBT is the only thing using M dash I don't know what to do about it

because this is such a core part of my identity but that's a big statement dash 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 dril that is generated by AI can be generated by AI that power is at anyone's fingertips tips. But truly the

the companies that are going to distinguish themselves are the ones that show their craft, that they show their true understanding of the product, the true understanding of their customer and

connect the two in meaningful ways. If

they can use AI to augment their efforts to make that happen, that's better than than subsuming their efforts. So to

build taste, you know, there's there's plenty of past episodes that you yourself have recorded that get into building that work. But to me, that is going to be a a real differentiator for

not only great marketers, but great companies to just to stand out in the field. There's a a concept that I love

field. There's a a concept that I love that recently I learned from GMO at at Verscell. He calls it exposure hours as

Verscell. 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 get increase your exposure hours to great stuff because that is how you build

taste. I love that it's such a simple

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 the world. It's not

particularly dealflow news or competitive news or anything like that but is things that we have seen that resonated with us for whatever reason.

along these lines of not overrelying on JGBT AI tools for writing and creativity feels like there's going to be a big issue with people just starting earlier in their career where they just like

never learn how to do the thing and they just rely really heavily on chat and tools like that to write to email to communicate well I guess is there do you have any advice for folks that are early

career just like how to find that balance of over not overlying but still leveraging these tools I think there's two schools of thought

here. One is that sort of the domain

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

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

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

itself changing. And so if you're not leveraging some of these tools, you will be putting yourself at a disadvantage.

But understanding the underlying mechanics, you know, this is why I would still be a very firm believer in in STEM education is that you understand the fundamental concepts 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.

Yeah. easier said than done because there's all these tools now and you're just like, "Hey, I need to write a report for school." Like, I guess I could just maybe I'll this time I'll just ask JPT to 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.

You if 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 um how to apply them.

That's something that stuck with me from my chat with Toby Lucky from Shopify. We

were chatting about just like what is the most important things to uh incubate in your child and his answer I loved which is just uh which curiosity and I love that. Yeah. And that's what you're

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

more deeply 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. That reminds me, I wanted to

else has. That reminds me, I wanted to come back to sort of close out our conversation. I wanted to come back to

conversation. I wanted to come back to pricing strategy. I had that in my notes

pricing strategy. I had that in my notes here and I haven't gone back to it. Uh

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

AI product. What are some tips some piece of advice to think this through?

Any general frameworks use? Again

there's no playbook. So the 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 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-s served 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 was

ACV deals. And so that trade-off was really hard to make. And so the only way we could do it was through experimentation and piloting to build conviction. So I would say AI is no

conviction. So I would say AI is no different in that you kind of have to test the market to see what works. Uh is

it a seedbased 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 to go off of. 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 seedbased pricing or usage based pricing wild indeed I want to actually follow this uh insight you had around retool that's really interesting so yeah what was so you uh

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 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 and 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

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

self-hosted. It was that for a variety of different reasons, regardless of your company's size, you might want self-hosted. So that insight kind of led

self-hosted. So that insight kind of led us to say, hey, where is the delineation here? Because the sales team should be

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.

Awesome. Okay, two final questions before we get to a very exciting lightning round. I'm going to take you

lightning round. I'm going to take you to a couple recurring segments on this podcast. The first is AI corner. And

podcast. The first is AI corner. And

with AI corner, what I try to get to is some way that you have figured out to use an AI tool in your work to do better work to do faster work to be more

efficient. Is there something there that

efficient. Is there something there that you could share? And if not, that's also totally cool. Oo, it is it is hard to

totally cool. Oo, it is it is hard to pick because there's not many things I don't use AI for these days. And often

times 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 their environment, their competitive landscape. We can do that

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

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 um the ability to mix AI tooling that accelerates work that you're already doing and then AI based tools that unlock superpowers that wouldn't

otherwise be available to you unless you're going deep into you know Google groups archives or talking to people across the organization to pull out things that are inside of their brain.

that kind of institutional knowledge being made more accessible by AI is actually more powerful sometimes than than the tools themselves. And in fact even at OpenAI, it's one of the things

that we advised most enterprises to invest in first is their own operational efficiency rather than just the AI magic dust they could sprinkle on top of their

product experience for their customers.

Awesome. Okay, final segment of the podcast we call fail corner. And the

idea here is we got 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

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

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?

Again, this question is hard because there's so many things to choose from as as potential examples here. And you're

absolutely right, Lenny, and 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

remembers it. It was ahead of its market. We launched it back in 2014. It

market. We launched it back in 2014. It

was supposed to be the platform with which e-commerce companies would tap into social commerce, you know, the buy buttons if you 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 as much as one side of the marketplace or you might have some conviction that you need to put something into the market for a particular moment in time, the timing of

the market really matters and the timing of multiple parties coming together to make a platform work really matters. And

so the learning here was like we hadn't gone deep enough into the market dynamics. We hadn't done enough user

dynamics. We hadn't done enough user research. Did people really want this?

research. Did people really want this?

And if they did, what were their alternatives? What was the stacks that

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 uh 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 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 the

history and now may be a good time to try something like that. Basically, a

cryptocurrency platform to send money internationally for free." What a what a dream that would be. Okay, Carria, is there anything else you wanted to share or maybe uh something you wanted to

remind people of from what we've talked about? Just to leave folks with a final

about? Just to leave folks with a final nugget before we get to our 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 it seems like there's a playbook for everything. There's a

framework for everything. But the

reality is the work is is hard. You have

to spend the hours and the time to really understand your customer. And

there's no replacement for that. And

there isn't going to be even with the advent of AI. And the other part of it is to deeply understand your product as well like what are you bringing to the table and not just your product but your

company's values your unique approach that you're bringing to the table and really be intentional and thoughtful about that because 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

together. With that, we've reached our very exciting lightning round. We have

five questions for you. Are you ready?

Hit me. Here we go. What are two or three books that you find yourself recommending uh 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

Obviously Awesome. She does a great job breaking down how to position a product from scratch if you've never had to do that. Um and she's just so great for her

that. Um and she's just so great for her real talk. So really highly recommend

real talk. So really highly recommend that. And then I

that. And then I love fiction. So I would say one of the

love fiction. So I would say one of the best reads in the last couple of years has been Meline Miller's Cersei, which is a retelling of a Greek myth. So

lyrical pros, beautiful writing. Highly

recommend. Love the combo. April

Dunford, we're huge fans of her on the podcast. She's been on twice. Uh I think

podcast. She's been on twice. Uh I think her book is in my background. Uh we'll

link to her episodes and mine. Oh wow.

Okay. So cool. Yeah, she's the best. Uh

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 weigh the spoilers. Uh, but yeah, keep going. It's

spoilers. Uh, but yeah, keep going. It's

amazing. Do you have a favorite product you recently discovered that you really love? Granola for meeting notes. I I

love? Granola for meeting notes. I 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

Granola. And I'll give a plug. You get a year free of granola if you become an annual subscriber of my newsletter. Uh

for not just you, but your whole company up to some limit. Check out

lenniesnewletter.com and click bundle and sign up and you get granola. Uh, so

cool. Help, buddy. It's helping Granola and me, I guess. Yeah, it's great. Okay

thank you. Uh, 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. 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 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 uh I I could not espouse that philosophy enough. I love that this isn't because I

enough. 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 uh other people perceiving how something did and setting

their expectations correctly.

Final question. Okay, we already talked about the mdash, but I want to ask you again uh like what I'm finding is so the story here is basically people have discovered JGBT is using M dashes a lot which are like these long dashes that

you have to use like special couple letters on the keyboard to use. Uh, 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 Chad GBT. There's like

content that has M dashes they assume isn't real. Uh, will you continue using

isn't real. Uh, will you continue using M dashes in spite of all this? I have

begrudgingly reduced my usage of M dashes, but 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

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. It's It's option shift minus. Option

in. It's It's option shift minus. Option

shift. I have to like type it. I can't

conceptualize in my head. Uh yeah. And

then there's like actual rules for when an M dash is the right thing versus there dash and the Oxford comma. The two

core tenants of my toolbox. Is an Oxford comma where you add the comma at the end or you don't. You keep the comma at the end. Yeah, I'm all I'm all for that too.

end. Yeah, I'm all I'm all for that too.

It looks so weird without it. Uh but

there's also like another M like a shorter not M dash I guess it's called something else, right? There's like M dash. Yeah, and that's for ranges of

dash. Yeah, and that's for ranges of numbers. Okay. Okay. I love that you

numbers. Okay. Okay. I love that you know all this. Okay. Well, with that Critica, this has been so fun and so awesome. Thank you so much for being

awesome. Thank you so much for being here. Two final questions. Where can

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?

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 upand cominging 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 way for

chat. And then what's the best way for them to reach out to you? Is it just on your website? Yes, please. Amazing.

your website? Yes, please. Amazing.

We'll link to that in the show notes.

Critica, thank you so much for being here. Thank you for having me. Bye

here. Thank you for having me. Bye

everyone. Thank you so much for listening. If you found this valuable

listening. If you found this valuable you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider

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

lennispodcast.com. See you in the next

lennispodcast.com. See you in the next episode.