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AI Engineer August 26, 2026 19m

Reverse-Engineering the AI Buyer — Aliisa Rosenthal, Acrew Capital

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  1. >> Hi everyone. My name is Alyssa and I >> Hi everyone. My name is Alyssa and I joined a little research lab called joined a little research lab called joined a little research lab called OpenAI a little over four years ago. OpenAI a little over four years ago. OpenAI a little over four years ago. When I joined it was When I joined it was When I joined it was you know a couple million in revenue. We you know a couple million in revenue. We you know a couple million in revenue. We had a self-serve API. We had some had a self-serve API. We had some had a self-serve API. We had some developers who found it and swiped a developers who found it and swiped a developers who found it and swiped a credit card and started building. Over the next few years I helped grow Over the next few years I helped grow the organization to several hundred the organization to several hundred the organization to several hundred people, grow our revenue to several people, grow our revenue to several people, grow our revenue to several billion on the enterprise side and and billion on the enterprise side and and billion on the enterprise side and and launched multiple products. So I really launched multiple products. So I really launched multiple products. So I really had the opportunity to be at the had the opportunity to be at the had the opportunity to be at the bleeding edge of bringing this somewhat bleeding edge of bringing this somewhat bleeding edge of bringing this somewhat alien technology to organizations from alien technology to organizations from alien technology to organizations from startups to massive enterprises and I'm startups to massive enterprises and I'm startups to massive enterprises and I'm going to share a little bit about what I going to share a little bit about what I going to share a little bit about what I learned along the way. So I think most organizations typically So I think most organizations typically have said okay, I'm ready to build out have said okay, I'm ready to build out have said okay, I'm ready to build out my go-to-market organization. I'm going my go-to-market organization. I'm going my go-to-market organization. I'm going to hire a bunch of sales people. I'm to hire a bunch of sales people. I'm to hire a bunch of sales people. I'm going to hire RevOps. I'm going to hire going to hire RevOps. I'm going to hire going to hire RevOps. I'm going to hire sales engineers and I'm going to build sales engineers and I'm going to build sales engineers and I'm going to build out my sales organization and then I'm out my sales organization and then I'm out my sales organization and then I'm going to figure out where the going to figure out where the going to figure out where the bottlenecks are and I'm going to add AI bottlenecks are and I'm going to add AI bottlenecks are and I'm going to add AI or I'm going to add automation to figure or I'm going to add automation to figure or I'm going to add automation to figure out how to scale this thing. out how to scale this thing. out how to scale this thing. My current advice to founders is do the My current advice to founders is do the My current advice to founders is do the opposite. So start with what you can opposite. So start with what you can opposite. So start with what you can automate. Start with there's so many automate. Start with there's so many automate. Start with there's so many tools available now in 2026 for a modern tools available now in 2026 for a modern tools available now in 2026 for a modern go-to-market or sales organization that go-to-market or sales organization that go-to-market or sales organization that have never been available before which have never been available before which have never been available before which really turns the entire playbook on its really turns the entire playbook on its really turns the entire playbook on its head. And you'll find that a lot of head. And you'll find that a lot of head. And you'll find that a lot of traditional sales leaders are very used traditional sales leaders are very used traditional sales leaders are very used to coming in and hiring a really big to coming in and hiring a really big to coming in and hiring a really big team and augmenting everything with team and augmenting everything with team and augmenting everything with humans, bringing in sales operations, humans, bringing in sales operations, humans, bringing in sales operations, sales engineers, lots of sales people, sales engineers, lots of sales people, sales engineers, lots of sales people, BDRs, SDRs. You can do so much of this BDRs, SDRs. You can do so much of this BDRs, SDRs. You can do so much of this through an automated approach now. So my

  2. through an automated approach now. So my through an automated approach now. So my my advice to founders is build the my advice to founders is build the my advice to founders is build the machine first before you build the team. machine first before you build the team. machine first before you build the team. Figure out what you can automate. Figure Figure out what you can automate. Figure Figure out what you can automate. Figure out where the bottlenecks are and what's out where the bottlenecks are and what's out where the bottlenecks are and what's broken and then add humans on top of broken and then add humans on top of broken and then add humans on top of that to get through those bottlenecks. that to get through those bottlenecks. that to get through those bottlenecks. So, just a story about how this played So, just a story about how this played So, just a story about how this played out at OpenAI. So, we launched ChatGPT out at OpenAI. So, we launched ChatGPT out at OpenAI. So, we launched ChatGPT in the end of 2022. When we launched it, in the end of 2022. When we launched it, in the end of 2022. When we launched it, we had no enterprise features we had no enterprise features we had no enterprise features whatsoever. And I got bombarded with whatsoever. And I got bombarded with whatsoever. And I got bombarded with organizations saying, "Hey, everyone in organizations saying, "Hey, everyone in organizations saying, "Hey, everyone in my company is using ChatGPT. Can I get my company is using ChatGPT. Can I get my company is using ChatGPT. Can I get SSO? Can I get an NDA? Can I get an SSO? Can I get an NDA? Can I get an SSO? Can I get an NDA? Can I get an invoice?" I had none of these things. I invoice?" I had none of these things. I invoice?" I had none of these things. I had no enterprise features whatsoever. had no enterprise features whatsoever. had no enterprise features whatsoever. Uh so, over the next few months, I Uh so, over the next few months, I Uh so, over the next few months, I begged and begged and begged our begged and begged and begged our begged and begged and begged our technical team, "Can we build an technical team, "Can we build an technical team, "Can we build an enterprise version of this product and enterprise version of this product and enterprise version of this product and we build some enterprise features?" And we build some enterprise features?" And we build some enterprise features?" And finally, 9 months later, we got finally, 9 months later, we got finally, 9 months later, we got approval. Now, over that 9-month time, approval. Now, over that 9-month time, approval. Now, over that 9-month time, the companies that had been the loudest, the companies that had been the loudest, the companies that had been the loudest, the companies that had gotten to me, the companies that had gotten to me, the companies that had gotten to me, were the bigger companies, were the were the bigger companies, were the were the bigger companies, were the large enterprises. So, I thought, "Okay, large enterprises. So, I thought, "Okay, large enterprises. So, I thought, "Okay, we should go out and build a really we should go out and build a really we should go out and build a really high-end product for all these high-end product for all these high-end product for all these enterprises that want to use us." So, we enterprises that want to use us." So, we enterprises that want to use us." So, we added every bell and whistle. We made it added every bell and whistle. We made it added every bell and whistle. We made it lightning fast. It was a very expensive lightning fast. It was a very expensive lightning fast. It was a very expensive product that we shipped. We went up product that we shipped. We went up product that we shipped. We went up market. We went way up market right out market. We went way up market right out market. We went way up market right out the gate. And, you know, we did fine. We the gate. And, you know, we did fine. We the gate. And, you know, we did fine. We We did pretty well. Um, you know, and We did pretty well. Um, you know, and We did pretty well. Um, you know, and and I think for most companies we did and I think for most companies we did and I think for most companies we did great. Uh but after about a quarter, we great. Uh but after about a quarter, we great. Uh but after about a quarter, we said, "Well, we should probably also said, "Well, we should probably also said, "Well, we should probably also offer a self-serve version. Not everyone offer a self-serve version. Not everyone offer a self-serve version. Not everyone wants to opt into this heavy sales wants to opt into this heavy sales wants to opt into this heavy sales process and start with these really high process and start with these really high process and start with these really high price points." So, then we released our price points." So, then we released our price points." So, then we released our self-serve motion in January of 2024, so self-serve motion in January of 2024, so self-serve motion in January of 2024, so about about about 4 months after our enterprise version,

  3. 4 months after our enterprise version, 4 months after our enterprise version, and it just completely cannibalized our and it just completely cannibalized our and it just completely cannibalized our enterprise business. Uh it grew so much enterprise business. Uh it grew so much enterprise business. Uh it grew so much faster. It turns out most people just faster. It turns out most people just faster. It turns out most people just didn't want to talk to a salesperson, didn't want to talk to a salesperson, didn't want to talk to a salesperson, and our mid-market SMB sort of and our mid-market SMB sort of and our mid-market SMB sort of self-serve business was much higher self-serve business was much higher self-serve business was much higher growth than our and then our heavy growth than our and then our heavy growth than our and then our heavy enterprise business. So, it frustrated enterprise business. So, it frustrated enterprise business. So, it frustrated the sales reps cuz now they had to the sales reps cuz now they had to the sales reps cuz now they had to compete with self-serve. It sort of compete with self-serve. It sort of compete with self-serve. It sort of cannibalized the customer base. They cannibalized the customer base. They cannibalized the customer base. They sometimes they preferred to just sometimes they preferred to just sometimes they preferred to just move into the cheaper self-serve option. move into the cheaper self-serve option. move into the cheaper self-serve option. And so, that was a really valuable And so, that was a really valuable And so, that was a really valuable lesson. We should have launched with lesson. We should have launched with lesson. We should have launched with self-serve first, listen to feedback self-serve first, listen to feedback self-serve first, listen to feedback from our customers and what we they from our customers and what we they from our customers and what we they weren't getting from the self-serve weren't getting from the self-serve weren't getting from the self-serve product, and then figured out how to add product, and then figured out how to add product, and then figured out how to add build a more expensive enterprise build a more expensive enterprise build a more expensive enterprise offering, and then hire the team to sell offering, and then hire the team to sell offering, and then hire the team to sell it. So, we did it all backwards. Was a it. So, we did it all backwards. Was a it. So, we did it all backwards. Was a really really valuable learning really really valuable learning really really valuable learning experience, and from there we decided experience, and from there we decided experience, and from there we decided not to do that again. For every other not to do that again. For every other not to do that again. For every other product we launched at OpenAI, we made product we launched at OpenAI, we made product we launched at OpenAI, we made sure to to do it self-serve first, learn sure to to do it self-serve first, learn sure to to do it self-serve first, learn where we needed to tack on humans and where we needed to tack on humans and where we needed to tack on humans and add them. Uh the other thing I'll mention, and uh Uh the other thing I'll mention, and uh you know, uh if Everett's still here, you know, uh if Everett's still here, you know, uh if Everett's still here, nice uh shout-out to him. We used Clay nice uh shout-out to him. We used Clay nice uh shout-out to him. We used Clay at OpenAI, and it was really really at OpenAI, and it was really really at OpenAI, and it was really really useful for us. So, in the beginning, we useful for us. So, in the beginning, we useful for us. So, in the beginning, we were just completely overwhelmed with were just completely overwhelmed with were just completely overwhelmed with inbound, which I know sounds like such a inbound, which I know sounds like such a inbound, which I know sounds like such a champagne problem, but it was me and champagne problem, but it was me and champagne problem, but it was me and four sales sales reps, and we were four sales sales reps, and we were four sales sales reps, and we were getting, you know, 10,000 inbound a day.

  4. getting, you know, 10,000 inbound a day. getting, you know, 10,000 inbound a day. I mean, it was just the most staggering I mean, it was just the most staggering I mean, it was just the most staggering problem to deal with this tidal wave of problem to deal with this tidal wave of problem to deal with this tidal wave of inbound. And, you know, if I could go inbound. And, you know, if I could go inbound. And, you know, if I could go back in time, there's so much I would back in time, there's so much I would back in time, there's so much I would have done differently. I would have, have done differently. I would have, have done differently. I would have, first of all, added way more fields to first of all, added way more fields to first of all, added way more fields to our sign-up form, like phone number, our sign-up form, like phone number, our sign-up form, like phone number, because eventually when we did catch up because eventually when we did catch up because eventually when we did catch up and we built all the automation and we and we built all the automation and we and we built all the automation and we figured out how to handle these leads, I figured out how to handle these leads, I figured out how to handle these leads, I didn't have a lot of information to go didn't have a lot of information to go didn't have a lot of information to go follow up with people. So, add a very follow up with people. So, add a very follow up with people. So, add a very in-depth sales form. It can be optional, in-depth sales form. It can be optional, in-depth sales form. It can be optional, but if people are willing to give you but if people are willing to give you but if people are willing to give you their phone number, you should get it, their phone number, you should get it, their phone number, you should get it, cuz at some point you might want to call cuz at some point you might want to call cuz at some point you might want to call them or have AI call them. Um so, gather them or have AI call them. Um so, gather them or have AI call them. Um so, gather as much info as you can. Try to respond as much info as you can. Try to respond as much info as you can. Try to respond to everyone, and I I you know, I wish I to everyone, and I I you know, I wish I to everyone, and I I you know, I wish I would have done this, at least just sent would have done this, at least just sent would have done this, at least just sent some email out saying, "Hey, we hear some email out saying, "Hey, we hear some email out saying, "Hey, we hear you. We don't have our enterprise you. We don't have our enterprise you. We don't have our enterprise product ready yet. You're on our product ready yet. You're on our product ready yet. You're on our waitlist. You're on our list. Tell us waitlist. You're on our list. Tell us waitlist. You're on our list. Tell us XYZ about what you're looking for." Just XYZ about what you're looking for." Just XYZ about what you're looking for." Just some sort of automated email campaign to some sort of automated email campaign to some sort of automated email campaign to make them feel like we cared. Because make them feel like we cared. Because make them feel like we cared. Because when we finally did launch our when we finally did launch our when we finally did launch our enterprise product 9 months later, enterprise product 9 months later, enterprise product 9 months later, almost every company went out and talked almost every company went out and talked almost every company went out and talked to you said, "Well, you never got back to you said, "Well, you never got back to you said, "Well, you never got back to me." And I went out and I brought to me." And I went out and I brought to me." And I went out and I brought Microsoft Copilot. Um so, that was a Microsoft Copilot. Um so, that was a Microsoft Copilot. Um so, that was a that was a really hard lesson. that was a really hard lesson. that was a really hard lesson. Um and then similarly on outbound, uh Um and then similarly on outbound, uh Um and then similarly on outbound, uh you know, there's lots of great tools you know, there's lots of great tools you know, there's lots of great tools out there now. Clay is one of them. I out there now. Clay is one of them. I out there now. Clay is one of them. I hear really great things about Nooks. Uh hear really great things about Nooks. Uh hear really great things about Nooks. Uh there are really wonderful tools to there are really wonderful tools to there are really wonderful tools to start researching, sequencing, dialing, start researching, sequencing, dialing, start researching, sequencing, dialing, and automate as much as the outbound and automate as much as the outbound and automate as much as the outbound pipeline gen as you can, so your reps pipeline gen as you can, so your reps pipeline gen as you can, so your reps can focus on the qualified leads and the can focus on the qualified leads and the can focus on the qualified leads and the high value conversations.

  5. So, this is my biggest advice to any So, this is my biggest advice to any company starting to build their company starting to build their company starting to build their go-to-market motion is just make it easy go-to-market motion is just make it easy go-to-market motion is just make it easy on your buyers. on your buyers. on your buyers. Uh don't give them homework. Don't make Uh don't give them homework. Don't make Uh don't give them homework. Don't make them go and fill out a form or if you them go and fill out a form or if you them go and fill out a form or if you can avoid it, integrate something can avoid it, integrate something can avoid it, integrate something without you hand-holding them through without you hand-holding them through without you hand-holding them through that. Never say, "Hey, go do these five that. Never say, "Hey, go do these five that. Never say, "Hey, go do these five things and then come back to me." or "Go things and then come back to me." or "Go things and then come back to me." or "Go ask this person about this and come back ask this person about this and come back ask this person about this and come back to me." You do as much of the work for to me." You do as much of the work for to me." You do as much of the work for them. You hand-hold them through that. them. You hand-hold them through that. them. You hand-hold them through that. Maybe that means you have to set up Maybe that means you have to set up Maybe that means you have to set up hackathons and come in their office and hackathons and come in their office and hackathons and come in their office and do it with them in person. Um maybe that do it with them in person. Um maybe that do it with them in person. Um maybe that means you have to set up some sort of means you have to set up some sort of means you have to set up some sort of Zoom session and do it live with them. Zoom session and do it live with them. Zoom session and do it live with them. But, whatever you do, don't send your But, whatever you do, don't send your But, whatever you do, don't send your buyer away to do something and wait for buyer away to do something and wait for buyer away to do something and wait for them to come back because you lose total them to come back because you lose total them to come back because you lose total control of the sales cycle and it makes control of the sales cycle and it makes control of the sales cycle and it makes everything take longer. everything take longer. everything take longer. Secondly, remove as much friction as you Secondly, remove as much friction as you Secondly, remove as much friction as you can in the buying process. Fewer options can in the buying process. Fewer options can in the buying process. Fewer options is better on pricing. Make the paperwork is better on pricing. Make the paperwork is better on pricing. Make the paperwork easy and fast. Make the approval flow as easy and fast. Make the approval flow as easy and fast. Make the approval flow as manageable as possible. We've already manageable as possible. We've already manageable as possible. We've already talked about investing in self-service, talked about investing in self-service, talked about investing in self-service, doing that up front before you add on doing that up front before you add on doing that up front before you add on humans. And the other thing I'll hammer humans. And the other thing I'll hammer humans. And the other thing I'll hammer home is to avoid pilots at all cost. Um home is to avoid pilots at all cost. Um home is to avoid pilots at all cost. Um and this is something that comes up when and this is something that comes up when and this is something that comes up when I talk to founders a lot is they say, I talk to founders a lot is they say, I talk to founders a lot is they say, "We are stuck in pilot hell. We've got "We are stuck in pilot hell. We've got "We are stuck in pilot hell. We've got all of these pilots going on. None of all of these pilots going on. None of all of these pilots going on. None of them are converting. They're so much them are converting. They're so much them are converting. They're so much work." Or if they do convert, it just I work." Or if they do convert, it just I work." Or if they do convert, it just I have to run an entire sales process all have to run an entire sales process all have to run an entire sales process all over again. I sell the pilot. I invest over again. I sell the pilot. I invest over again. I sell the pilot. I invest really heavily in managing the pilot.

  6. really heavily in managing the pilot. really heavily in managing the pilot. And then I have to start all over again And then I have to start all over again And then I have to start all over again from scratch once the pilot I get a yes from scratch once the pilot I get a yes from scratch once the pilot I get a yes to move forward on the sales cycle. So, to move forward on the sales cycle. So, to move forward on the sales cycle. So, use pilots sparingly. They should be not use pilots sparingly. They should be not use pilots sparingly. They should be not the default, but the option for your the default, but the option for your the default, but the option for your most valuable, most valuable, most valuable, uh highest paying, biggest revenue uh highest paying, biggest revenue uh highest paying, biggest revenue opportunities. Now, how do you get out opportunities. Now, how do you get out opportunities. Now, how do you get out of a pilot? Because every customer will of a pilot? Because every customer will of a pilot? Because every customer will ask you for one. They'll say, "I need to ask you for one. They'll say, "I need to ask you for one. They'll say, "I need to try this out. I need a POC. It's part of try this out. I need a POC. It's part of try this out. I need a POC. It's part of our process. I need to validate this our process. I need to validate this our process. I need to validate this works in my environment. It meets my works in my environment. It meets my works in my environment. It meets my needs. We have, you know, all of these needs. We have, you know, all of these needs. We have, you know, all of these things we need to validate and check things we need to validate and check things we need to validate and check on." Just remember, as soon as you give on." Just remember, as soon as you give on." Just remember, as soon as you give someone access to your product, you're someone access to your product, you're someone access to your product, you're giving away a lot of power and leverage giving away a lot of power and leverage giving away a lot of power and leverage in the deal cycle. So, there's lots of in the deal cycle. So, there's lots of in the deal cycle. So, there's lots of ways to get around these objections ways to get around these objections ways to get around these objections without a pilot. You can introduce them without a pilot. You can introduce them without a pilot. You can introduce them to another customer. You can do an eval to another customer. You can do an eval to another customer. You can do an eval on on part of their data. You can do a on on part of their data. You can do a on on part of their data. You can do a demo with their custom data and you do demo with their custom data and you do demo with their custom data and you do it over Zoom rather than handing them it over Zoom rather than handing them it over Zoom rather than handing them access to it. You can give them an access to it. You can give them an access to it. You can give them an opt-out clause. It's not something you opt-out clause. It's not something you opt-out clause. It's not something you do when you're a giant company, but when do when you're a giant company, but when do when you're a giant company, but when you're a startup, you can get away with you're a startup, you can get away with you're a startup, you can get away with these things. So, sign a contract, you these things. So, sign a contract, you these things. So, sign a contract, you have 90 days to opt out if it doesn't have 90 days to opt out if it doesn't have 90 days to opt out if it doesn't meet your needs, and that shifts the meet your needs, and that shifts the meet your needs, and that shifts the onus of trying out the product and onus of trying out the product and onus of trying out the product and validating it uh onto them cuz the the validating it uh onto them cuz the the validating it uh onto them cuz the the clock is ticking on them now. Uh so, it clock is ticking on them now. Uh so, it clock is ticking on them now. Uh so, it gives you a lot more control over the gives you a lot more control over the gives you a lot more control over the deal. And then another one I like to do deal. And then another one I like to do deal. And then another one I like to do is I say, "Well, our normal uh contracts is I say, "Well, our normal uh contracts is I say, "Well, our normal uh contracts are 3 years, but we'll do a 1-year POC are 3 years, but we'll do a 1-year POC are 3 years, but we'll do a 1-year POC with you." So, there's all kinds of ways with you." So, there's all kinds of ways with you." So, there's all kinds of ways to sort of negotiate your way around a to sort of negotiate your way around a to sort of negotiate your way around a POC without putting tons of resources POC without putting tons of resources POC without putting tons of resources and getting stuck in them.

  7. and getting stuck in them. and getting stuck in them. The other thing is security. Security is The other thing is security. Security is The other thing is security. Security is where deals tend to stall out and die where deals tend to stall out and die where deals tend to stall out and die over time. Uh there's a lot you can over time. Uh there's a lot you can over time. Uh there's a lot you can automate now. There's so many wonderful automate now. There's so many wonderful automate now. There's so many wonderful tools on the market to build these trust tools on the market to build these trust tools on the market to build these trust portals where, you know, companies can portals where, you know, companies can portals where, you know, companies can come in and they can auto sign an NDA. come in and they can auto sign an NDA. come in and they can auto sign an NDA. They can self-serve for your pen test They can self-serve for your pen test They can self-serve for your pen test and security documentation. There's AI and security documentation. There's AI and security documentation. There's AI products that can auto fill out your products that can auto fill out your products that can auto fill out your security questionnaires. So, automate a security questionnaires. So, automate a security questionnaires. So, automate a as much as the security as you can, and as much as the security as you can, and as much as the security as you can, and most companies will tell you, "Oh, I most companies will tell you, "Oh, I most companies will tell you, "Oh, I need to get on a call. I need to talk need to get on a call. I need to talk need to get on a call. I need to talk for 2 hours." Push back on that. You for 2 hours." Push back on that. You for 2 hours." Push back on that. You know, push them towards your trust know, push them towards your trust know, push them towards your trust portal and then make them come to you portal and then make them come to you portal and then make them come to you and say, "Here, you know, here's what I and say, "Here, you know, here's what I and say, "Here, you know, here's what I couldn't find. Here's what wasn't couldn't find. Here's what wasn't couldn't find. Here's what wasn't available. Here's why I need a call." available. Here's why I need a call." available. Here's why I need a call." And try to automate security because a And try to automate security because a And try to automate security because a lot of it really can be automated now, lot of it really can be automated now, lot of it really can be automated now, which is really really uh speeds up the which is really really uh speeds up the which is really really uh speeds up the sales cycle. Um so, another thing we learned, another Um so, another thing we learned, another expensive story, and this goes back to expensive story, and this goes back to expensive story, and this goes back to sort of building the Porsche before the sort of building the Porsche before the sort of building the Porsche before the Prius, is we built this this really Prius, is we built this this really Prius, is we built this this really high-end product, this enterprise high-end product, this enterprise high-end product, this enterprise product, and we set the price really product, and we set the price really product, and we set the price really high. We set it initially ChatGPT high. We set it initially ChatGPT high. We set it initially ChatGPT Enterprise was $60 per user per month.

  8. Enterprise was $60 per user per month. Enterprise was $60 per user per month. Now, we were really the first ones on Now, we were really the first ones on Now, we were really the first ones on the market, and we didn't know what the market, and we didn't know what the market, and we didn't know what pricing was going going pricing was going going pricing was going going Uh so, we we basically priced it Uh so, we we basically priced it Uh so, we we basically priced it according to how expensive it was for us according to how expensive it was for us according to how expensive it was for us to serve it. And then all the other to serve it. And then all the other to serve it. And then all the other products came out on the market, Copilot products came out on the market, Copilot products came out on the market, Copilot and Gemini and Anthropic at a much lower and Gemini and Anthropic at a much lower and Gemini and Anthropic at a much lower price point. And we realized we had set price point. And we realized we had set price point. And we realized we had set the price too high. the price too high. the price too high. So, we eventually went and we did lower So, we eventually went and we did lower So, we eventually went and we did lower the price. And what we did, we changed the price. And what we did, we changed the price. And what we did, we changed the model to basically a license fee a the model to basically a license fee a the model to basically a license fee a bare fee to use the product and then bare fee to use the product and then bare fee to use the product and then move to usage base. And then we just saw move to usage base. And then we just saw move to usage base. And then we just saw a the barrier to entry went down. So, we a the barrier to entry went down. So, we a the barrier to entry went down. So, we had so many more companies signing had so many more companies signing had so many more companies signing licenses and signing contracts with us. licenses and signing contracts with us. licenses and signing contracts with us. And then usage went up over time as more And then usage went up over time as more And then usage went up over time as more as we started the barrier to entry went as we started the barrier to entry went as we started the barrier to entry went down. Because when it was $60 per month, down. Because when it was $60 per month, down. Because when it was $60 per month, organizations would come in and say, organizations would come in and say, organizations would come in and say, well, I'm only buying this for a subset well, I'm only buying this for a subset well, I'm only buying this for a subset of my team or only for my developers or of my team or only for my developers or of my team or only for my developers or only for my investors. I'm not going to only for my investors. I'm not going to only for my investors. I'm not going to buy buy it for my whole company. It's buy buy it for my whole company. It's buy buy it for my whole company. It's too expensive. But once we lowered the too expensive. But once we lowered the too expensive. But once we lowered the threshold, it spread like wildfire. threshold, it spread like wildfire. threshold, it spread like wildfire. Everyone started using it and it was a Everyone started using it and it was a Everyone started using it and it was a much better pricing model that we much better pricing model that we much better pricing model that we learned the hard way. I know over time learned the hard way. I know over time learned the hard way. I know over time now seats are out. This this has become now seats are out. This this has become now seats are out. This this has become common knowledge. We learned it the hard common knowledge. We learned it the hard common knowledge. We learned it the hard way. And I also know that now usage is way. And I also know that now usage is way. And I also know that now usage is also getting pushed back as company push also getting pushed back as company push also getting pushed back as company push back on as companies are seeing cost of back on as companies are seeing cost of back on as companies are seeing cost of usage skyrocket. There's easy ways usage skyrocket. There's easy ways usage skyrocket. There's easy ways around this. So, you could for example, around this. So, you could for example, around this. So, you could for example, cap. You can say, hey, we have a cap. You can say, hey, we have a cap. You can say, hey, we have a dashboard. You can cap your spend per dashboard. You can cap your spend per dashboard. You can cap your spend per month. Most companies don't end up using month. Most companies don't end up using month. Most companies don't end up using that, but they like to know that it's that, but they like to know that it's that, but they like to know that it's there. You can cap certain employees there. You can cap certain employees there. You can cap certain employees spend. But people like the idea that spend. But people like the idea that spend. But people like the idea that it's a low barrier to entry. People can it's a low barrier to entry. People can it's a low barrier to entry. People can use it. If they're using it, ideally use it. If they're using it, ideally use it. If they're using it, ideally they're getting value out of it. And they're getting value out of it. And they're getting value out of it. And then there's ways to handle the then there's ways to handle the then there's ways to handle the objections of what if the cost spirals objections of what if the cost spirals objections of what if the cost spirals out of control.

  9. All right. So, we've talked about All right. So, we've talked about building the machine. When do you hire building the machine. When do you hire building the machine. When do you hire the humans? When do you start bringing the humans? When do you start bringing the humans? When do you start bringing on sales people? Sales people are on sales people? Sales people are on sales people? Sales people are expensive. expensive. expensive. You know, they're that's a big hire. You know, they're that's a big hire. You know, they're that's a big hire. They're they're you know, how do you They're they're you know, how do you They're they're you know, how do you know when the time is right? It's know when the time is right? It's know when the time is right? It's basically when you're starting to hit basically when you're starting to hit basically when you're starting to hit you've gone as far as you can in your you've gone as far as you can in your you've gone as far as you can in your sales process and you're really having a sales process and you're really having a sales process and you're really having a lot of companies saying, I just need to lot of companies saying, I just need to lot of companies saying, I just need to talk to somebody whether it's I need a talk to somebody whether it's I need a talk to somebody whether it's I need a demo. I just need to look someone in the demo. I just need to look someone in the demo. I just need to look someone in the eye and build the trust here. And you're eye and build the trust here. And you're eye and build the trust here. And you're going to have that as you start to move going to have that as you start to move going to have that as you start to move up market naturally. Bigger companies up market naturally. Bigger companies up market naturally. Bigger companies are going to want to look shake the are going to want to look shake the are going to want to look shake the hands of a human and have a conversation hands of a human and have a conversation hands of a human and have a conversation with them. On that note, I will say with them. On that note, I will say with them. On that note, I will say avoid the pull-up market as long as you avoid the pull-up market as long as you avoid the pull-up market as long as you can resist it because once you get a big can resist it because once you get a big can resist it because once you get a big customer, they'll come and they'll say, customer, they'll come and they'll say, customer, they'll come and they'll say, "I can spend a million dollars, 10 "I can spend a million dollars, 10 "I can spend a million dollars, 10 million dollars with you." And it's very million dollars with you." And it's very million dollars with you." And it's very tempting to want orient your whole tempting to want orient your whole tempting to want orient your whole business around that. They will take so business around that. They will take so business around that. They will take so many of your resources. As soon as you many of your resources. As soon as you many of your resources. As soon as you have this enterprise customer, they will have this enterprise customer, they will have this enterprise customer, they will take so many of your legal, security, take so many of your legal, security, take so many of your legal, security, product, engineering, sales resources. product, engineering, sales resources. product, engineering, sales resources. So, you want to be really, really picky So, you want to be really, really picky So, you want to be really, really picky about who those first big enterprise about who those first big enterprise about who those first big enterprise partners are. Eventually, you're going partners are. Eventually, you're going partners are. Eventually, you're going to need, most likely, not everyone, but to need, most likely, not everyone, but to need, most likely, not everyone, but eventually you most likely are going to eventually you most likely are going to eventually you most likely are going to need some humans to help have these need some humans to help have these need some humans to help have these conversations.

  10. conversations. conversations. So, who do you hire? You hire someone So, who do you hire? You hire someone So, who do you hire? You hire someone who is AI native, who really gets AI, who is AI native, who really gets AI, who is AI native, who really gets AI, who lives it, who can authentically sell who lives it, who can authentically sell who lives it, who can authentically sell it because they're really bought into it because they're really bought into it because they're really bought into it. This is not a reseller right now, it. This is not a reseller right now, it. This is not a reseller right now, but this is more and more becoming the but this is more and more becoming the but this is more and more becoming the norm with sellers, with account norm with sellers, with account norm with sellers, with account executives. Uh you want them to practice executives. Uh you want them to practice executives. Uh you want them to practice what they preach, you want them to be what they preach, you want them to be what they preach, you want them to be efficient, you want them to be bought efficient, you want them to be bought efficient, you want them to be bought into the culture of your organization. into the culture of your organization. into the culture of your organization. Why do you need them? I'm calling this Why do you need them? I'm calling this Why do you need them? I'm calling this the revenge of the steak dinner. As more the revenge of the steak dinner. As more the revenge of the steak dinner. As more and more of this becomes automated, as and more of this becomes automated, as and more of this becomes automated, as you have the automated outbound, the you have the automated outbound, the you have the automated outbound, the automated demo, the automated security automated demo, the automated security automated demo, the automated security checklist, more and more companies are checklist, more and more companies are checklist, more and more companies are craving in-person times with humans. So, craving in-person times with humans. So, craving in-person times with humans. So, conferences, conference booths work conferences, conference booths work conferences, conference booths work really well, dinners work really well. really well, dinners work really well. really well, dinners work really well. And they're, by the way, not that And they're, by the way, not that And they're, by the way, not that expensive to set up a dinner with some expensive to set up a dinner with some expensive to set up a dinner with some buyers, some customers, some prospects. buyers, some customers, some prospects. buyers, some customers, some prospects. It's a very effective tool, and you do It's a very effective tool, and you do It's a very effective tool, and you do still at this at this moment in time still at this at this moment in time still at this at this moment in time need humans to run those dinners. need humans to run those dinners. need humans to run those dinners. Uh so, let's talk a little bit about Uh so, let's talk a little bit about Uh so, let's talk a little bit about hiring sales people and how you pay hiring sales people and how you pay hiring sales people and how you pay them. Um this comes up a lot at OpenAI. them. Um this comes up a lot at OpenAI. them. Um this comes up a lot at OpenAI. We were notorious because we still have We were notorious because we still have We were notorious because we still have not given out comp plans. Um it was not not given out comp plans. Um it was not not given out comp plans. Um it was not necessarily my intention to wait this necessarily my intention to wait this necessarily my intention to wait this long. I just kind of kept kicking the long. I just kind of kept kicking the long. I just kind of kept kicking the can down the road and saying, can down the road and saying, can down the road and saying, "Eventually, I'll pay commission." And "Eventually, I'll pay commission." And "Eventually, I'll pay commission." And then we just the team got bigger and it then we just the team got bigger and it then we just the team got bigger and it got harder and harder. I do think OpenAI got harder and harder. I do think OpenAI got harder and harder. I do think OpenAI is finally about to put in commission.

  11. is finally about to put in commission. is finally about to put in commission. Uh but we we made a we made it really Uh but we we made a we made it really Uh but we we made a we made it really far without any comp plans. I would not far without any comp plans. I would not far without any comp plans. I would not necessarily say that is the right path necessarily say that is the right path necessarily say that is the right path for every company to follow. I think for every company to follow. I think for every company to follow. I think OpenAI could get away with that because OpenAI could get away with that because OpenAI could get away with that because of the equity packages and the way the of the equity packages and the way the of the equity packages and the way the company was increasing in value, but in company was increasing in value, but in company was increasing in value, but in general, it's really hard to hire the general, it's really hard to hire the general, it's really hard to hire the best enterprise sellers in the market if best enterprise sellers in the market if best enterprise sellers in the market if you don't pay a variable. That said, you you don't pay a variable. That said, you you don't pay a variable. That said, you can get away with it for your first few can get away with it for your first few can get away with it for your first few hires. Those first few sales hires are hires. Those first few sales hires are hires. Those first few sales hires are usually wired a little bit differently. usually wired a little bit differently. usually wired a little bit differently. They're there to build the company. They're there to build the company. They're there to build the company. They're there for the equity. They want They're there for the equity. They want They're there for the equity. They want to roll up their sleeves. They want to to roll up their sleeves. They want to to roll up their sleeves. They want to contribute. They're not necessarily as contribute. They're not necessarily as contribute. They're not necessarily as motivated just by commission and by a motivated just by commission and by a motivated just by commission and by a W-2. So, you can get away with it really W-2. So, you can get away with it really W-2. So, you can get away with it really for the first two or three sales hires. for the first two or three sales hires. for the first two or three sales hires. Eventually, you're going to want to hire Eventually, you're going to want to hire Eventually, you're going to want to hire kind of more coin-operated enterprise kind of more coin-operated enterprise kind of more coin-operated enterprise sellers. They're very motivated by the sellers. They're very motivated by the sellers. They're very motivated by the cash compensation, and so eventually cash compensation, and so eventually cash compensation, and so eventually you'll need to put in a comp plan. So, you'll need to put in a comp plan. So, you'll need to put in a comp plan. So, just I get this question a lot, so I just I get this question a lot, so I just I get this question a lot, so I just wanted to put it out there on how just wanted to put it out there on how just wanted to put it out there on how to think about building out comp plans. to think about building out comp plans. to think about building out comp plans. Simpler is better, but have upside for Simpler is better, but have upside for Simpler is better, but have upside for out-performers. out-performers. out-performers. Um so, I love this slide. I saw this Um so, I love this slide. I saw this Um so, I love this slide. I saw this early in my career in sales, and I just early in my career in sales, and I just early in my career in sales, and I just think it's um it's a really great think it's um it's a really great think it's um it's a really great reminder of what you're actually reminder of what you're actually reminder of what you're actually selling. You're not selling your tool.

  12. selling. You're not selling your tool. selling. You're not selling your tool. You're not selling your product. You're You're not selling your product. You're You're not selling your product. You're selling what that tool or that product selling what that tool or that product selling what that tool or that product does to your champion or your buyer. And does to your champion or your buyer. And does to your champion or your buyer. And this is where I do think humans are this is where I do think humans are this is where I do think humans are still very helpful. They're very good at still very helpful. They're very good at still very helpful. They're very good at value selling, and I think AI does still value selling, and I think AI does still value selling, and I think AI does still have some ways to go on value selling. have some ways to go on value selling. have some ways to go on value selling. So, until we totally crack that, I do So, until we totally crack that, I do So, until we totally crack that, I do think we're going to need those steak think we're going to need those steak think we're going to need those steak dinners, and we're going to need those dinners, and we're going to need those dinners, and we're going to need those humans to sell value. humans to sell value. humans to sell value. All right. So, that's me. You can grab a All right. So, that's me. You can grab a All right. So, that's me. You can grab a one-pager of this with that QR code. Um one-pager of this with that QR code. Um one-pager of this with that QR code. Um also really easy to find on LinkedIn. also really easy to find on LinkedIn. also really easy to find on LinkedIn. I'm the only one with my crazy spelling I'm the only one with my crazy spelling I'm the only one with my crazy spelling of a name with A L I I S A. Feel free to of a name with A L I I S A. Feel free to of a name with A L I I S A. Feel free to reach out if you have questions, and it reach out if you have questions, and it reach out if you have questions, and it looks like I have a couple minutes for looks like I have a couple minutes for looks like I have a couple minutes for Q&A here. Q&A here. Q&A here. >> Okay. How First question right here. >> Okay. How First question right here. >> Okay. How First question right here. >> Yeah, I uh >> Yeah, I uh >> Yeah, I uh Can you hear me? Can you hear me? Can you hear me? >> I can. >> I can. >> I can. >> Okay. Yeah, I was just curious about um >> Okay. Yeah, I was just curious about um >> Okay. Yeah, I was just curious about um you talked about the POCs and pilots you talked about the POCs and pilots you talked about the POCs and pilots should be the exception, but then should be the exception, but then should be the exception, but then there's also the self-serve first there's also the self-serve first there's also the self-serve first motion. How do you reconcile that? motion. How do you reconcile that? motion. How do you reconcile that? Because Because Because you know, the POC or pilot then becomes you know, the POC or pilot then becomes you know, the POC or pilot then becomes just do they get help when they go off just do they get help when they go off just do they get help when they go off and do self-serve? and do self-serve? and do self-serve? And they need your help to be And they need your help to be And they need your help to be successful. successful. successful. >> Great question. I am sort of thinking of >> Great question. I am sort of thinking of >> Great question. I am sort of thinking of PLG, so people coming and self-serving PLG, so people coming and self-serving PLG, so people coming and self-serving and just using your product is very and just using your product is very and just using your product is very different from a POC, which is usually a different from a POC, which is usually a different from a POC, which is usually a contracted period of time where they contracted period of time where they contracted period of time where they have access to your product and they have access to your product and they have access to your product and they have support and resources from your have support and resources from your have support and resources from your team and you're giving them sort of team and you're giving them sort of team and you're giving them sort of services and support along the way. So, services and support along the way. So, services and support along the way. So, you're right. That is access like you're right. That is access like you're right. That is access like self-serve access to your product is self-serve access to your product is self-serve access to your product is totally fine and great and you can stage totally fine and great and you can stage totally fine and great and you can stage gate that or limit that with gate that or limit that with gate that or limit that with um consumption, um consumption, um consumption, uh time box it, um or um

  13. uh time box it, um or um uh time box it, um or um uh feature gate it and those are all uh feature gate it and those are all uh feature gate it and those are all really valid ways to have people sort of really valid ways to have people sort of really valid ways to have people sort of build a natural PLG funnel into your build a natural PLG funnel into your build a natural PLG funnel into your product. When I talk about POCs, I'm I'm product. When I talk about POCs, I'm I'm product. When I talk about POCs, I'm I'm specifically referring to more handheld specifically referring to more handheld specifically referring to more handheld services uh oriented POCs that require a services uh oriented POCs that require a services uh oriented POCs that require a sales engineer or salesperson to sort of sales engineer or salesperson to sort of sales engineer or salesperson to sort of supervise. supervise. supervise. >> Hey Alyssa Roy. Um >> Hey Alyssa Roy. Um >> Hey Alyssa Roy. Um quick question on forward deployed quick question on forward deployed quick question on forward deployed engineers. How do you think about them engineers. How do you think about them engineers. How do you think about them fitting into the sales cycle? fitting into the sales cycle? fitting into the sales cycle? >> Yeah. I mean, in an ideal world, we >> Yeah. I mean, in an ideal world, we >> Yeah. I mean, in an ideal world, we wouldn't need them. Uh eventually, wouldn't need them. Uh eventually, wouldn't need them. Uh eventually, hopefully we get continual learning and hopefully we get continual learning and hopefully we get continual learning and these models can just figure out the these models can just figure out the these models can just figure out the inner organization and how to just inner organization and how to just inner organization and how to just immediately become smart. Uh I do think immediately become smart. Uh I do think immediately become smart. Uh I do think for now, the thing with a forward for now, the thing with a forward for now, the thing with a forward deployed engineer is on the one hand, deployed engineer is on the one hand, deployed engineer is on the one hand, they're expensive, they're hard to hire. they're expensive, they're hard to hire. they're expensive, they're hard to hire. I think there's something like 55,000 I think there's something like 55,000 I think there's something like 55,000 job wrecks for forward deployed job wrecks for forward deployed job wrecks for forward deployed engineers right now and about 5,000 engineers right now and about 5,000 engineers right now and about 5,000 people who know how to do that job. So, people who know how to do that job. So, people who know how to do that job. So, they're hard to hire. If they're you they're hard to hire. If they're you they're hard to hire. If they're you know, they're you're getting more and know, they're you're getting more and know, they're you're getting more and more of them available. more of them available. more of them available. The positive is they make the product The positive is they make the product The positive is they make the product really sticky cuz once you've invested really sticky cuz once you've invested really sticky cuz once you've invested in that sort of services element of in that sort of services element of in that sort of services element of we're going to have someone come and we're going to have someone come and we're going to have someone come and help you uh integrate the product, your help you uh integrate the product, your help you uh integrate the product, your customer is unlikely to go anywhere soon customer is unlikely to go anywhere soon customer is unlikely to go anywhere soon because they feel like they've got a because they feel like they've got a because they feel like they've got a customized tool that works uniquely for customized tool that works uniquely for customized tool that works uniquely for them. So, I would say obviously the in them. So, I would say obviously the in them. So, I would say obviously the in an ideal world, your product works an ideal world, your product works an ideal world, your product works without the forward deployed engineering without the forward deployed engineering without the forward deployed engineering uh cuz they are very hard to get right uh cuz they are very hard to get right uh cuz they are very hard to get right now, but the the positive is then you now, but the the positive is then you now, but the the positive is then you have a you have a sticky customer who's have a you have a sticky customer who's have a you have a sticky customer who's with you for a long time. So, if you can with you for a long time. So, if you can with you for a long time. So, if you can if you can find good forward deployed if you can find good forward deployed if you can find good forward deployed engineers, they they certainly do pay engineers, they they certainly do pay engineers, they they certainly do pay dividends.

  14. >> Hi Alyssa. Um >> Hi Alyssa. Um for startup working on like their first for startup working on like their first for startup working on like their first 10 customers, would you go like the clay 10 customers, would you go like the clay 10 customers, would you go like the clay route or would you do something else? route or would you do something else? route or would you do something else? >> Uh I'm sorry, when you say the clay >> Uh I'm sorry, when you say the clay >> Uh I'm sorry, when you say the clay route, what do you mean specifically? route, what do you mean specifically? route, what do you mean specifically? >> Like using something like clay for >> Like using something like clay for >> Like using something like clay for automated outbound. automated outbound. automated outbound. >> Got it. No, your first 10 customers are >> Got it. No, your first 10 customers are >> Got it. No, your first 10 customers are going to be different. Um they're going going to be different. Um they're going going to be different. Um they're going to be really more design partners. Um to be really more design partners. Um to be really more design partners. Um and they're going to need to be much and they're going to need to be much and they're going to need to be much more handheld. So, I I'm talking a more handheld. So, I I'm talking a more handheld. So, I I'm talking a little bit more when you're beyond the little bit more when you're beyond the little bit more when you're beyond the first sort of design partners and you first sort of design partners and you first sort of design partners and you have some product market fit and you're have some product market fit and you're have some product market fit and you're starting to scale the organization. For starting to scale the organization. For starting to scale the organization. For those first partners, you want to be those first partners, you want to be those first partners, you want to be very particular and picky about who you very particular and picky about who you very particular and picky about who you choose. On the one hand, it's it's sort choose. On the one hand, it's it's sort choose. On the one hand, it's it's sort of a gift to a company to let them be of a gift to a company to let them be of a gift to a company to let them be your design partner. There's exclusivity your design partner. There's exclusivity your design partner. There's exclusivity to it, there's scarcity to it. They to it, there's scarcity to it. They to it, there's scarcity to it. They really help give you a lot of feedback really help give you a lot of feedback really help give you a lot of feedback on your product, but you want someone on your product, but you want someone on your product, but you want someone who's going to work well with you, who's who's going to work well with you, who's who's going to work well with you, who's going to understand this is going to understand this is going to understand this is realistically where my product is. This realistically where my product is. This realistically where my product is. This is where my enterprise features are. Um is where my enterprise features are. Um is where my enterprise features are. Um so, you want to be thoughtful about who so, you want to be thoughtful about who so, you want to be thoughtful about who those first few customers are. One those first few customers are. One those first few customers are. One tactic I love to do on the design tactic I love to do on the design tactic I love to do on the design partner side is go to a company that has partner side is go to a company that has partner side is go to a company that has a great logo, but work on like their a great logo, but work on like their a great logo, but work on like their internal product or some sort of product internal product or some sort of product internal product or some sort of product that's not their main production, so that's not their main production, so that's not their main production, so that they're willing to take a little that they're willing to take a little that they're willing to take a little bit more risks with you and bypass some bit more risks with you and bypass some bit more risks with you and bypass some security processes, but then you get the security processes, but then you get the security processes, but then you get the logo on your site and you can go to logo on your site and you can go to logo on your site and you can go to companies and say, "Hey, I work with companies and say, "Hey, I work with companies and say, "Hey, I work with this company." And it opens the door to this company." And it opens the door to this company." And it opens the door to potentially sign a bigger agreement with potentially sign a bigger agreement with potentially sign a bigger agreement with that company over time.

  15. that company over time. that company over time. And I think we're at time here. Sorry. Ideally, they're relationships you Ideally, they're relationships you already have, either companies you've already have, either companies you've already have, either companies you've worked with or your investors are worked with or your investors are worked with or your investors are introducing you or they're you know, introducing you or they're you know, introducing you or they're you know, friends at at companies cuz you want friends at at companies cuz you want friends at at companies cuz you want these to be very friendly uh uh these to be very friendly uh uh these to be very friendly uh uh uh processes and experiments in the uh processes and experiments in the uh processes and experiments in the beginning. beginning. beginning. Great. All right. Thank you.

Summary

The main theme is about building a scalable go-to-market strategy for tech products, drawing on the speaker's experience at OpenAI. Key subjects include the evolution of AI technology and the traditional sales playbook versus an automated approach. The practical takeaway is to prioritize building an automated "machine" before hiring a large human team, focusing on efficiency and automation first to drive growth.

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