SaaStr 805: CRO Confidential - 5 Ways AI Has Already Changed SaaS Sales Forever with Perplexity's CBO. Hosted by Sam Blond

0:00Welcome to the official Sastr podcast where you can hear some of the best Sastr speakers. This is where the cloud meets. Up today on the Sastra podcast. Speed is the new mode, right? So if there's one takeaway, you have no excuse to not be moving faster, right? And really, you now have these superpowers at your fingertips. And I think something I like to tell folks is every question that you would ask in a meeting with some third party and an external party, you can be asking those questions of perplexity of different AIs in advance, right? So there's no excuse to not be informed. You should not actually be doing the discovery.

0:47You shouldn't be learning the discovery questions in real time. But I think the imperative is to move faster because your competitors are moving faster. Hey, everybody, get excited. We just hosted 10 ,000 of you at the Sastr Annual and AI Summit in the SFB area. It was insane. It was off the charts compared to last year. It was a deep dive on everything new, everything AI, everything go to market. And we're getting ready because Sastr AI is coming to London in December. It's Christmas with Sastr. On December 2nd and 3rd, we're bringing Sastr AI to the heart of Europe. This is your chance to connect with thousands of SaaS and AI executives, founders, and investors all sharing the secrets to scaling in the age of AI.

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2:55excited to be here another incredible saster annual big shout out to jason limkin and amelia and the whole saster team every year bigger and better than the last somehow thrilled to be here my name is sam blonde i have a series through saster called cro confidential i'm also the founder of a startup that's in stealth that's an end-to-end revenue platform. Enough about me. We have one of the coolest guests from one of the hottest tech companies in the world right now. Dimitri Shevilenko is chief business officer at Perplexity. I won't talk much about you or the business because I won't do it justice.

3:41Before we jump in, maybe just tell us a little bit about your background and tell us what Perplexity is. And then we're going to talk a lot about how folks should be leveraging AI in sales and more. Awesome. Well, thanks everybody for coming. Thanks, Sam, for doing this. Hopefully we have some fun. I'm Dimitri, CBO at Perplexity. For those that haven't tried Perplexity, it's an answer machine. You bring your hard questions and we do our best to answer them for you, grounding it in the high quality sources from the internet, from inside your organization, from high quality external sources. And it's been a real privilege to be part of the Perplexity journey.

4:21I started my career at Facebook, was at LinkedIn, was at Uber, had tastes of hyper growth and got addicted to that feeling and excited to be creating it once again with Perplexity. Awesome. Well, thank you for doing this. So let's see, coming into the show, I often do some research on the guests, listen to some podcasts, those sorts of things. For this one, I started with just asking Perplexity. It gave it a prompt around, this is who I am. This is a little bit about the show. This is my guest today, Dimitri and his role. What are the most important topics that we could include in the list of things to discuss today?

5:01Perplexity basically just built the show for us. They talk about AI coming for your job. This is one that I think is pretty quickly being disrupted. With that in mind, there are two really exceptional topics that I think you'll have maybe the most sophisticated view on than anyone in the world. The first is you're at this cutting edge AI company. You're also a former founder. And so one of the things that I want to do is talk about where we are today and how companies, specifically tech companies, should be leveraging AI within their go-to-market organizations. So that's topic one. We'll move on to the sort of intersection of product-led growth and sales-assisted customer acquisition.

5:45I think perplexity has a lot of revenue with a mix of sort of product-led or folks coming directly to the website and signing up, also sales-assisted. I think that's true across like, many if not most companies that are formed around AI and in B2B. So let's start with the former of the topics. If you are a startup founder today, you're starting a new business, you've been a startup founder before, most of what there is to know about AI's capabilities today, the products that exist in the market and more, what are the things that you are leveraging AI for as part of demand gen and customer acquisition?

6:27And then maybe what are some of the things that we aren't yet there? Yeah. I think we were talking about this backstage stage speed is the new mode right so the the one if there's one takeaway you have no excuse to not be moving faster right and really you now have these superpowers at your fingertips and you know I think something I like to tell folks is every question that you would ask in a meeting with some you know third party and an external party you can be asking those questions of perplexity of different AIs in advance, right? So there's no excuse to not be informed. You should not actually be doing the discovery, like you shouldn't be learning the discovery questions like in real time.

7:16Now we'll get into a tactic that I like to use that I think is the best of both worlds, but I think the imperative is to move faster because your competitors are moving faster. I get asked, you know, why is it that perplexity is in the position that we're in? And part of it is timing and part of it is execution speed. If we had, you know, we got lucky with timing, if we had founded the company six months before we did, GPT-3 would not have been good enough, the equivalent of it at that point in time. And we wouldn't have been able to create that initial magical experience of combining AI with the internet.

7:58If we had started six months later, there'd be somebody else on stage right now that would have like seized that moment. And so that's really kind of where I like to give advice for founders. Okay. That's awesome. So I think it's sort of the version of what I did with perplexity coming into this show. It's like, you're a founder or you're a sales rep. You have a meeting coming up, just prompt AI or perplexity with who you are, what your company does, who you're meeting with, what their role is, and ask them, like, how should we structure this call? What are the things that I should know going into the call?

8:36And so this is the sort of like meeting prep that used to be very manual that you can probably do in just a matter of seconds. And again, sort of like relating to preparing for this show, I saved probably 90 minutes to two hours on just sort of like prep for what are the things that we should talk about? Tell me about Dimitri just by prompting perplexity versus doing the listening to podcasts, a bunch of my own research. You're applying that same thing to meeting preparation. Yeah. And I think it's about just being with the time you saved, you actually then ask more questions, right? And going deeper.

9:11So what are perplexity's biggest challenges? Like, how have they tried to solve them? You know, once you're armed with the initial information, it should spark that curiosity. One of the most popular features in the product are the related questions that we show below the answer. Because the thing, you know, there's no end stop to knowledge and learning. The, you know, a good answer just begs more questions. and you actually want to, when you're then like going from meeting prep to the actual meeting, you want to carry that spirit with you. So what I like to do is I'll just share my screen and I will in real time start asking questions about the company that I'm talking to or the person, right?

9:55So it's like, hey, what are the biggest challenges company X is facing? How have they tried to solve them? So you kind of show your work in real time. And obviously it's easy for us to do it because it's showing our own product. But in some ways it's even more powerful for you all to do this because if you can prompt the right way and all of a sudden your solution, your product, your approach comes up in the AI generated answer or it points to that, man, that is authentic. That's powerful. It's transparent. And I've just seen that work really well. And I think that's a tactic of just in this new era, transparency is everything.

10:36And if a smart AI is pointing to a certain direction, that's going to help whoever you're meeting with gain conviction in that direction too. Okay. So I would categorize these things as combination of like meeting prep and meeting assistance that historically would take 10 to 20 times the amount of effort as it does today. Anything else that comes to mind before we sort of progress? Yeah, I mean, I think in general, at the earliest stages of startup development, and this isn't just using perplexity, but the rate at which you're prototyping and coming up with new concepts, getting feedback on them, that can all be accelerated dramatically, right?

11:21And so when you are then ready to put the pedal on the gas, you should have a lot more conviction and you've tried a lot more concepts. And so using tools like Cursor, we're going to have the ability to build mini apps and perplexity soon, or something's going to get announced called projects. It's not meant to be a coding replacement, but to quickly visualize different concepts and get feedback on them, that should no longer take a week, a month. That's like an hour. And you should be constantly running through your head. How can I do in one hour what used to take a day, in one day what used to take a week, in one week what used to take a month?

12:04And that's the right mental model here. Awesome. I'll add a little bit of my own color before we get into more mature businesses and how a company like Perplexity is leveraging the advancement of this technology. As an early stage founder myself, there are a few things within GoToMarket that I am leveraging today. The first is lead scoring. Historically, this used to be something that was pretty complicated that you would need maybe RevOps assistance with. and it was like very manual and very trial and error. Models are quite good at this today. So as you are building out your addressable market, the scoring of that addressable market, models are very good at.

12:49I think the second thing that I am taking advantage of, and again, like you're sort of behind if you aren't doing these things, is intent signals. So once you have a set of your database, it is scored based off of, you know, different tiers from a graphic information. you want to overlay intent signals on top of your scored database. So these are things like, where do I have connections that exist within buyers at these companies? Are they hiring for different roles? Whatever your individual intent signals are that you want to overlay on top of your addressable market, models are very good at that today.

13:25And there are several products that do this today. And then lastly, on the demand gen side, we're very good today at deciding the type of outreach to take advantage of given the account score and the intent signals. So if we want to prescribe, reach out to this account with this message through these channels because of these reasons. These three different steps here, score my database for me, overlay intent signals on top of my score database and then tell me what I should do to break into these accounts based off of the information that exists in these scores and intent signals. Models are very good at that today.

14:08And so these are things that I think like if you today aren't leveraging in go to market, acquiring customers, you're a little bit behind. And then you described the meeting prep, I think very well. Once you do have meetings on calendars, I think that the models are quite good at preparing you for that stuff. Okay, let's talk about as we get a little bit larger and introduce more complexity in the organization, potentially, you know, management structure and those sorts of things. How is a company like Perplexity taking it to the next level in terms of leveraging either your own technology or AI in general to do things that weren't possible even 12 months ago?

14:44Yeah. I think one mental model is to assume that using a tool like Perflexity and other AIs, you can get to 80 % of an expert level in a lot of fields that are not your profession. So a good example is when I receive a contract, instead of immediately kicking over to the lawyer, I run it through Perflexity and I prompt and I ask, hey, what are the likely issues here and what should I actually discuss with my counsel? And that way, when I'm actually engaged with it, I'm not just pretending to be a lawyer and then going off of what the AI says. I don't think that's where the technology is. I know some founders do operate that way, but we're talking about more mature organizations.

15:30And for them, it's really about making that lawyer's time more efficient so that when a business counterpart comes to them with an ask, it's focused, they've already done their homework, and you're not wasting time on the broad review and you're zeroing in on the most pertinent issues. And so then take that same approach and think about engaging with a colleague in marketing, a colleague in design. You're able to, whatever your zone of responsibility is and you need to interface with others, you're able to anticipate a lot of what they may help you with. And so then when you do approach them, you're saving both sides a lot of time, right?

16:10And that's where we see incredible efficiencies. I think there's also when you have templates, right? So say you need to generate a proposal and you have three or four really good examples. People love uploading those into Perplexity spaces and then prompting, hey, can you generate an example, a proposal in the same style, but for this other company? And where Perplexity really excels is we're able to pull in all the real-time information about that company, what's specific to them and preserve the style of your templates but update it and personalize it for that company, right? And you should never then just take that output and immediately hit send.

16:53That's not, I think that's, it's not about replacing human judgment and oversight. It's about saving you that time to get to the 80 % quality first draft and then making sure you're applying your judgment, your intuition on that last mile. Awesome. I'll add a little bit of color as well. I think, you know, as companies mature a little bit, you get more data. And I think you can train a model about historical engagements that you've had with different companies and data on sort of like how to position your product. One of the things that Jason brings up a lot is how, Jason from Sastr brings up a lot is how effective their AI is at sort of like selling for Sastr.

17:40They have on their website, come talk to the chatbot. And I think I'll go a little bit further on that specific example, but I think generally speaking, transactional commodity-like sales will be disrupted in ways that support has been disrupted, where more and more revenue will be generated from just pure models converting website visitors to revenue without the sales touch. And I think that will continue to become increasingly true. You know, as I said, Jason was raving about how Sastr is leveraging their AI and I wanted to like play with it, see what all the hype is about. Let's see, beginning of last week, I went to Sastr and it was just like, hey, it feels like I'm pretty late, but is there still any sponsorships that I could take advantage of for next week's annual?

18:36And interestingly, what the model did is something that I think a sales rep would never do. And it sort of like downsold me. And what I mean by that was, you know, it sort of outlined here are the types of sponsorships that you can still move forward with that are available. Like I actually would, I being the model would recommend that you move forward with like either a gold booth, a silver sponsorship, or one of these brand type sponsorships, because one of the more advanced sponsorships, I don't know if it was the platinum or what it was exactly. It was like, you know, it's going to be pretty tough for you to take advantage of all that that that sponsorship level has to offer, given that we're eight days away from the event.

19:20And And that just built a lot of trust with the AI that I was speaking to. It's the type of experience that I just can't imagine that is what a sales rep would be recommending. Because, of course, they want to maximize the amount of revenue that the company generates and ultimately their commission. So I think that is maybe some proof of models and AI replacing salespeople, especially at the sort of transactional or almost commodity-style sales. Other end of the spectrum, you have the, I don't know, Endurals of the world that are selling weapons to the government. Probably need a human for that for the foreseeable future and then everything in between.

20:05Just building on that, I think the most essential quality for AI products and AI first products, as you project out, is what you were referring to, which I call trust. And you really have to trust a salesperson to have confidence they're not selling you something you don't need. But the trust threshold for an AI is even greater. And that informs everything we do at Perplexity. how do we create and preserve trust with our users? And trust will be the scarce asset of the agentic internet. And a lot of the products are built on top of it. So it's easy to create AIs that manipulate people, but that's a very short-term strategy.

20:52And for folks that want to build for the long-term, you have to build trust in at the foundation level of your product and how you prompt these different AIs. Yeah, I think that's smart. And then the second thing that comes to mind as companies mature a little bit, it's in the category of converting demand or opportunities to revenue. So closing revenue. And you might be a founder that manages some salespeople. You might be a sales leader that manages a team of salespeople. And this typically manifests in what I would describe as pipeline reviews where this can either be ad hoc or casual, where it's sort of like, you know, how's the opportunity with perplexity going?

21:34And you get an update from the sales rep. Over time, it becomes a little bit more formalized where, you know, my experience, and this was true even up to something like 12 months ago, you have this incredibly sophisticated RevOps influence process around, you have a 30 minute meeting with each of your sales reps. And in that meeting, there is within your CRM, all of the deals that have the sales rep notes that are like ready in different categories for you to talk about, you know, each of the sort of risks and, you know, highest probabilities with the different deals. And then through that, you kind of get to a forecast and, you know, everything is like so perfect about this process.

22:16And RevOps has set up this like beautiful spreadsheet in CRM. The only problem is it's entirely wrong. and you have a sales rep that is adding their own subjective experience about the account. They may want to influence the sales manager to think that the deal is going to close, or they may be forgetting about what actually happened on the call. And back to your point around trust, today, you should have a model that is reading all communication with the buyer, the opportunity, the customer, and that's over generally email, you also should have an AI that is joining all of your calls. And the AI should be the one that is preparing for that meeting.

23:00And so when you come in, it's not actually the sort of like sales rep subjective information about the opportunity. This is like very matter of fact, you have a prompt given all of the data that you have in the model. What are the risks about this deal? What do you think the probability of this deal closing is? What are the suggestions that you have for the sales rep? And so if you are not doing this today with a model, this like pipeline review, sort of pipeline hygiene type application, you are a bit behind in something that wasn't totally possible 12 months ago. Yeah. The one thing that you can rely on in terms of the direction of AI progress is the context windows will expand, right?

23:45You'll be able to feed more into the prompt and get a useful output. Right now, yeah, they claim million tokens, 10 million tokens. When you start going up to that size of input, the quality deteriorates on the output, but that's not, you know, you have to assume it will get better. And yeah, you'll be able to just feed in, not necessarily train a new model, but just in the prompt, pass in every conversation you've had with a potential client and get that honest readout and benchmark it against the other prospects. Okay, we're moving just so fast with the progression of the technology and in the way that people are coming up with applying it.

24:28And we talked about a lot of these things that even 12 months ago, they were either less good than they are today, certainly less trustworthy or not possible. and in your seat being at truly the cutting edge of you probably having even access to things that aren't available publicly today you know if we're sitting here this time next year i think it's you know really hard to project out beyond 12 months what are the types of things that you're excited about that we can expect over you know the course of the rest of this year yeah i like to answer that by saying what won't change because in some ways that's a harder challenge and i think the you know going back to where we started coming up with the right questions to ask will become the critical skill right and you can say that's a form of like prompting but preserving the spark of curiosity and knowing where to take the next question that's because the answers will keep getting smarter, the products of perplexity will be better at incorporating many different sources, but it won't solve the cold start challenge, right?

25:43And so the cold start spark, that's the thing to focus in on. That's the thing that you can project will remain an evergreen problem. I think where we want to take the technology is to become a lot more proactive rather than being reactive, right? So instead of you having to always ask for the update of what's happening with this account, we're able to detect those changes that are meaningful and surface that to you, right? And whether that be your personal life, your professional life, transcending there, having these technologies become more personalized, become more proactive. I think that's what I would expect 12 months from now.

26:23Awesome. I'll try and layer in a couple tactical things that I think will change with the way that companies, how companies leverage technology. I talked about the different piecemeal things that today models are very good at. Scoring accounts, overlaying intent signals, determining what the best outreach strategy to ultimately generate a meeting and close revenue is. you know today these things sort of manifest in like a very piecemeal approach where you have maybe one product or service or one approach to doing the account scoring and then you have to sort of like check the work and see if it's correct and then you have like a different model different company different product that is doing the intent signals then you have a different model or product ever you want to think about that's doing the outreach strategy i think there will be a sort of like unified platform that comes together that takes all of these sort of disparate piecemeal processes and basically combines them.

27:31So you can effectively say like, this is my TAM, I want meetings. And the output can be, these things are still happening behind the scenes, but they're all happening in one sort of unified end-to-end platform. And I think because of that, what will start to happen for technology companies, for technology founders, so much more of the success of the business will be predicated on finding product market fit, like delivering customer value rather than being exceptional at developing and scaling go-to-market because I think that the models are going to start to become really good at that. And so for technical folks, I think that's hopefully music to your ears where it's like, you can really focus on solving customer problems, building the product, finding product market fit.

28:21And gosh, the risk around hiring the right SDR leaders and teams is far more abstracted away because the technology can get so much better at this stuff. Yeah. I mean, I think we're a good example of how this may play out. We have around over 5 ,000 enterprise clients for Prophexity enterprise pro and we have five sellers and so that i mean that also speaks to like the plg motion of having a consumer facing version of perplexity is very popular and that effectively reaches every enterprise that could potentially become an enterprise customer but i think that's there's a version of that that's true for many businesses how do you have use ai to bridge that kind of enterprise version of what you want to sell with the easy to get the 80-20 of the value consumer accessible version that may distribute itself.