We're Engineers. Here's Why We Chose Sales.

Hello everyone, and welcome to The Play by Quotain I'm your host, Jason He, co-founder of Quotain And today I'm joined by Alexander Talamonti CEO and co-founder of Quotain. Alex, normally you're interviewing salespeople, but we have a special episode today, don't we?

Yeah, it's pretty exciting. I'm glad to be, in the guest seat today. I'm just excited to see kind of how that goes. Jason's gonna be joining me in some future episodes when we talk with guests who he's primarily interacted with before. So we thought it was a good idea to introduce him to everyone who doesn't already know him.

Definitely. normally in these podcasts, you're interviewing salespeople who have scaled sales teams from zero to hundreds of millions of dollars, right? So it's a nice change of pace today. We'll be discussing more recent topics within AI, sales, and startups and seeing, our backgrounds, more of an engineering product background, how that changes our views on things pertaining to sales. I guess Alex, any immediate reactions towards coming into sales from a non-traditional background?

Yeah, so for people who don't know my background already, I started my career more or less in an engineering role. Actually, out of high school, I had an internship as like a QA engineer at this company called Kenari Adaptive Learning. So that was like the very first job that I had. I worked at Cava as people who check my LinkedIn would know. and I For the vast majority of my time, I had software engineering roles. So I did do operations at Phia. Yeah. I also did some product management kind of stuff at a few companies, but primarily software engineering. So software and product, not a lot of sales experience. And I've said this in some posts before, but sales isn't really something that you get to learn in. school either. I I haven't really encountered many classroom settings where sales is something that's been practiced. And so did definitely learn a lot of it on the job being founder of Quotain with you. Yeah. Right? I think as an engineer, you like to look at things and say, hey, this is a process that I can optimize. How do I start doing that? And that's the lens that I initially took towards looking at sales. s definitely still believe it. That's why quotain exists. But as any salesperson you'd ask would respond, it's also very much an art. Yeah. Right? And I think that's for engineers like myself and like someone like yourself who also didn't really come from a sales background. Probably where it gets a little bit difficult to initially bridge that gap. A lot of like repetitions and like Pattern recognition.

Definitely. yeah, I also came from a very different background, product focused.

Yeah, do you wanna you wanna explain what it was quickly?

Yeah, so I came from a product background, worked at companies like Reddit and Datadog with you, funny enough. also worked on various other industries, you know, mainly recruiting was a big space I was kinda in, which is kind of like sales, you know. I think everything kind of boils down to sales at the end the day, but sales as a role is still pretty different from other sorts of roles calling themselves, we do a bit of sales here or there. I think it's definitely an aspect of just human persuasion in all sorts of roles, and they just kind of call that sales. But I think sales is just the whole orchestration. of how do you get someone in the door, improve value, and continue to deliver value so that they'll continue to work with you. So I think there's some differences, some similarities here, but the question I want to ask you, Alex, is how did you fall into sales as the path you want to take the company in?

Well it a joint decision, of course, and not just me. But we recognized as software engineers whose job or career was fundamentally disrupted by AI, that Sales ends up becoming probably the most important part of founding a company. Obviously, you need some sort of technical idea, some differentiator, some insight, but without getting that to market, you're not you're not helping anyone. Yeah. Right? And so we recognized early on that as engineers, sales was the area that we needed to work on. Very common for YC founders. Have historically selected for technical founders and said, we believe we can teach these technical people sales. And we thought about how much AI had been able to disrupt software engineering. I mean, the job has completely changed. Yes. Some people would argue it's a solved problem at this point.

I don't know if it's completely solved, but it's very different than what it was when you were at least working the

Sure. I when I was a data dog back in 2024, I still had to read the code, right? I honestly like probably

Most engineers probably.

aren't reading code these days, right? Sales is like, in my opinion, still very much the same as it was fifteen years ago. I wouldn't say that about lead generation per se. I think that's a an area that's been targeted pretty substantially by AI, and you can see a number of different companies that have, you know, had varying levels of success there. But once you're actually having human to human conversation, which is The part of sales that actually gets the deals closed. It's pretty much the same as it's been 15 years ago, probably thousand years ago. Yeah. Right? Like it's just kind of, hey, are we solving a problem for you? Does our solution do that? are you willing to pay for it? Is it worth more than that problem is worth to you? Right. And then navigating all that and all the complexities with it. So we wanted to see like AI is transforming everything. How can we think about what a future looks like where sales is fundamentally using AI to its full extent. Yeah. And what does that look like? How can we build towards it?

Alex, I'm curious, we went through Y C, speaking from your experience and also just what you've learned, leading sales for this long time, what advice would you give to, YC founders who are in the batch right now or just finished up, who are still struggling to figure out sales?

It's a very good question. It certainly depends on who you're selling to. I'm gonna be speaking from a B2B kind of experience and specifically from a B2B software kind of experience. We don't sell to the government right now. we don't really sell to consumers either. So there's my disclaimer. Yeah. But I think one of the key things to realize is that with sales, the very first thing you have to do is just start getting out there. Right? I don't think anyone ever feels ready to go and start selling. YC certainly makes the argument that you need to go and launch as soon as possible. And that's more marketing, but it's it's the same idea, which is that before you feel ready, that's the right time to start selling. some people sell even before they have a product, sometimes even before they have an idea, although that's kind of I don't know what you're selling in that scenario. you know, the very first thing is to kind of like take a new mindset of like, okay. I don't need to be ready to start selling. I just need to go and start talking to people. but if we want to like think about some more practical things, I would say one, I definitely would start with a YC launch if you're a YC founder, but even if you're not just starting with like launching on LinkedIn, it's marketing, but marketing and sales are incredibly interlaced.

Revenue.

Revenue, right? Like if we think just more from a revenue perspective, that's a great way to start building your inbound funnel, Because if you have an idea that at least some people are willing to be early adopters for, then you'll start getting that feedback immediately. Yeah. And what you want to optimize for early on as a founder who is still kind of figuring out like pre-PMF, you want to optimize for just having as many relevant conversations as possible. And I qualify it with relevant because talking to your mom and dad, if they're not your ICP or in your industry obviously isn't going to be what you need, but you should be trying to talk to as many of the people who would either be users of or buyers of your product as you can.

Yeah, that's really interesting. I guess we've definitely fallen to that pitfall ourselves before. But I'm curious here, let's say you're able to get a hold of, your ICP and it's more of a feedback chat rather than an actual selling conversation. What's your delineation here on how to have founders move from discovery, customer discovery to actual like sales discovery?

Yeah, that's a good question. I think from the very early chats that you're having, I wouldn't I wouldn't be surprised if they are just feedback chats. Right? That being said, that LinkedIn post, right, that should actually be bringing in proper sales conversations. Because rarely are people going and they see your cool LinkedIn YC launch and they're like, hey, like, I want to reach out to you to give you some feedback on like what I think is wrong with your product. Like that's not why they're reaching out, right? They're reaching out because usually these folks are like pretty Early adopters of technology, they like to keep tabs on what the newest startups are doing, and they're like, hey, this YC company just launched something that resonates with me. That's again a wonderful opportunity to have these sales conversations. But I'll use a tactic that we've used, for instance, as an example here. So we, Jason and I, have booked a lot of meetings with folks using boardy, funnily enough. go boardy. and there's definitely like a trap there where if You say outright, hey, I'm gonna go and I'm trying to sell to you. Yeah, they're probably just not gonna pick up, right? Because like they're they don't wanna get pitched. You don't wanna get pitched either. It's a double opt-in, so you're r you're run you're running that risk as well. but otherwise you do fall into that trap of like having feedback conversations. I think the two things to kind of take away from that are one, if you are having a feedback conversation, try and turn it into some sort of way to get intros to other folks. Like a partnership. Right, exactly. Because you wanna you wanna approach these conversations as hey, I'm actually trying to provide you value as well. So feedback you're actually usually extracting value from someone. So they're they're giving to you. Yep. So you want to think about how you can give to them when you're doing these conversations.

Some examples of how you give in gave in the past.

So there's certainly the opportunity to try and strike up referral partnerships with folks if you have a common customer, And it's like, okay, maybe they have other needs that they that could be fulfilled through some of your YC connections, That's a nice way to offer up something. as a founder, you are building your network in this industry. And so these folks, whoever they are, for us it's salespeople, but like As you are building up your network, they probably also want to talk to people who are in their industry. That's that's kind of why they're talking to you. So that's the easiest way to say, hey, look, we had a great conversation. I'm opening my network up to you. if there's anyone that you know isn't in my network that you wanna talk with, I'm more than happy to make that introduction. It might not be sales, it might just be they wanna chat about some problem that they're having or whatnot. But I think that's a good way to start.

Mm-hmm. Yeah, that's super interesting. I think really having that like serving mindset of like, yo, what value can we really provide to you and can we earn the right to, you know deliver enough value to work together and see, what comes out of that. I think like as founders you really have to do things that don't scale. So if you were to recommend the founder, like various channels for them to explore, obviously it differs by market here, but you know, do you recommend them going to conferences or flying to see their prospects or you know, what else would you recommend these founders to do to really leverage their reputation and you know do things that don't scale?

I think that yes, conferences is great. Everyone knows the every founder at least knows the Patrick Collison, John Collison installation, Where they pulled up to people's houses and installed Stripe for them. that's the classic example. It's still a good one. Nope. Right. I think conferences is kind of like the popular version of that nowadays where you go to a a conference and you're able to say, Hey, I'm the founder of this company, I I can solve your problems. I can be really custom. I can give you special deals. that's that's things that like an SDR who would go to the same conference wouldn't have the authority to say. So that's something that's pretty important. I think even doing cold calls. You and I have been doing a bunch of cold calls recently, people seem to respond a little bit better to you being the founder of a company. It's just a little bit more interesting than they respect

They respect it a little bit.

it a little bit more. and So you're able to probably get on conversations just a little bit more as well. those are some good examples of like where being the founder definitely helps and it's like as a founder then you should leverage the fact that you're a founder by mentioning it, right? You don't want to say, Hey, I'm Alex with Quotain, I'm Alex the founder of Quotain People feel more special being talked to directly by the founder. Okay. I wanna flip it on you a bit, Jason. What do we think the future of sales actually looks like?

It's a good question. I think it's, you know, very hard to make definite guesses because there's always a step change every six months in the effectiveness of AI, right? If you were to tell us there what Fable was was in late twenty twenty five, my mind would probably be blown. If you told us that there is an open weight model of Fable level that is available when Fable was getting released and, you know, secured by Anthropic, I would also have been mind blown, you know. And obviously there's consequences there, but To bring that back to the point of what does sales look like? I still think sales is fundamentally human. Because sales is, you're developing trust between two parties here. And the trust is, can this other party help me? It's not always, functions and features, because often when you go as a rep, you're pitching functions and features. But at the end the day, it's who do they trust the most to solve their problem? It's kind of how I think it. And I think it's Pretty hard to trust an AI to solve your problem. Or not not to solve your problem, maybe, but to trust them as a party. I don't know. What do you think about that?

Well yeah, this is something you and I talk about a decent amount. Trust, in my opinion, requires the ability for the party to knowingly misbehave and feel consequences for that. I think in particular, as a human, you have a reputation. And the price of breaking that reputation is a loss in trust. Now If ChatGPT tells me that I should just mix bleach and vinegar, and then I do that and I die, ChatGPT will say, oops, you're absolutely correct. I shouldn't have mentioned you should do that. Yeah. And there's really nothing, like, you know, yeah, you can go sue up in the eye whatever, but that's not like again, that's that's towards a human, Like there's there's n ChatGPT doesn't feel bad that it violated your trust. It might say it does, but at least as far as we're aware right now, it doesn't. And that weightiness, that actual emotional cost is why trust can in my opinion only happen between two people.

Yeah. I guess, to answer more of the original question of what does AI in sales actually look like in the future, we're already seeing certain jumps with, you know, people are getting better at prospecting. They're using tools like Clay or the AI versions competitors of Clay to do prospecting a lot easier. They're able to find their exact ICP. They're able to automate a lot of the busy, like process oriented work that was happening beforehand, and potentially even able to pass certain judgments on. As well, not all, because at the end of the day, your prospect really depends on your judgment and your view of your leads list. But you can have it figure out the best way to find out certain data. let's say you have a super niche industry and certain signals around. Maybe you want to find Google images that show how much corn is in someone's like you know, farm, right? You can use that to you can use more creative signals now that are able to write scripts and automate than you previously weren't able to do. I think that really unlocks the difference between now and like what sales was like three, four years ago where it was very much more manual, people were just, you know, going off normal signals. but going beyond that, right, I feel like sales hasn't really transformed with AI. And there's many reasons.

I can tell you why. I based on what you just said, I had an idea. I think that what you just described in terms of sales and like being able to do these all kind of more creative things. What it's done is it's actually simply lifted up the playing field, if you will. Now everyone can do these creative plays. Before maybe you had like if you had a team of 20 or something, you could you could make this script that goes through and looks at Google image data and finds the amount of corn that someone has and you can sell your you tortilla chip solution But now that everyone can run these creative plays, the question then becomes again, how do you differentiate yourself?

Yeah. It's a really, really hard problem. And I think that honestly combines with some of marketing as well because it's like, you've seen the startups that are flying planes across San Francisco or are buying all the seats at a baseball game in Cincinnati because they're like ICP is r resides there, So I think a lot of these more creative ways that combine like marketing sales together are what ultimately builds trust in makes you stand out. if you just host a normal event or just another dinner without anything interesting, I think it's gonna be tougher and tougher for, people to say, I'm gonna spend my free time doing this, or I'm gonna spend post work time going to something this and build trust with a vendor. but, kind of to change directions here, I honestly think though, a lot of the more transactional sales, will probably become automated. And, there's already this notion of like self-serve, probably like growth and That's already existing, but for some reason, I don't know why, certain smaller tier transactional like products, let's say you're on like a starter plan for payroll software. Okay. you just want to know that it does your payroll. Yeah and maybe does some of the legal entity stuff for you. And you just have a few questions you want answered. maybe you'll ask AI, maybe you'll ask, the sales rep. And sometimes sales rep may or may not know, but they're definitely gonna say, yeah, we can do that because they're trying to sell you that solution. Yeah. At the end of the day, it's a very transactional interaction because you need a payroll provider here. Yes. And they obviously provide this clear thing to you. And, I've definitely hopped on these calls before. It's like, you know, we schedule like thirty minutes, I think I take ten minutes because, you I have some questions I'm asking and they can show me a demo of the platform. Yeah, but

I you already knew you wanted to buy it though.

I don't really know if I want to see a whole demo of the platform. As a founder, I just want to know that it works for me and it like does what I need it to in this very specific slot. Yeah.

So do you think that having an AI sales rep that could go through those specific questions with you, maybe even on email or just sends you videos, right? do you think that would be a better user experience for your needs as a founder?

I think so, because a lot of my purchasing decisions are done async. And what that means is like it's a combination of, looking at GEO, AEO, whatever you want to call it, and having that influence, how would you rank these paper providers for my specific use case? I trust my like ChatGPT or Claude a lot more than, someone else's some vendor specific Chat GPT or Claude. So I want myself to do that research first. And then it's like, okay, there's certain questions or answers that I Can't get unless I talk to the provider specifically. And maybe they don't want to release that to the public. Well,

Yeah.

and you know, I'll be forced to take a discovery call just so I can understand this information. Even though it's very clear that you know I want this at what if if it's like a good price compared to its competitors, right? Because ultimately that's how I'm making my buying decisions. So, if the vendor here is like, yes, this person is qualified, we want to share pricing information with them. Then it's like, okay, I probably want to ask them very specific questions, get those answered, and see if that meets my criteria to move on. I think what it does leave is me as like a buyer now. Do I have so much more power where I just like, let's say, all my payroll providers have this sort of AI thing, I can just ask them to compare and just make a decision from there? Or is it a more complex interaction where they will say, hey, it looks like you were talking to, let's say payroll providers A's bot. And we'll match that. We actually make it a little bit deeper, right? That would be interesting. Because it's like they're giving up some of their alpha by having this AI seller being available to you.

Maybe that's why they wouldn't do then.

Exactly. So it's tough to say, but once again, it's like you really don't really know what the future might hold. But I think for some transactional deals where people do want to ask questions and don't try They'll probably look to research and just get something quick out of like an AI that can respond instantly rather than wait like a day, a week to actually have the call.

I I think that makes a lot of sense. I think another example if you think from a consumer lens could be insurance, It's just okay, realistically, for rentals insurance, lemonade already does this. I've never spoken once to a lemonade rep. Yeah. Even though I know that other insurance providers, I believe, do require you to actually call someone. and that's why lemonade is nice because Ideally I never to deal with flood in my New York high rise or whatever anyway, But I'll get the insurance and I'm just trying to like check a check a box. And so that's the scenario where it's like, okay, yeah, I don't really need to talk to someone. But like where then are there scenarios where you still need to have a conversation

I think it's when the scenario isn't as cut and dry and it's very specific. You want something customized towards your specific scenario. So it's like, let's say there's a super complex piece of software and let's say there's a lot of moving modules and pieces I can get recommended, you know.

you're having a custom setup or custom implementation for

And obviously they will probably be using AI on their side to help make those recommendations. But it's like, how can I figure out what's the right fit for my situation? Because I think gone are the days of companies trying to fit a one size fits all sort of solution onto every company. And more and more custom tiers are coming about. People are doing more forward-deployed motions for these larger enterprises. People are making things more customizable. And I think that, will really shift how people think about selling. Because ultimately it's like What do we have that's delivering value for you? Because going back to that server mindset that we were talking about, It's like what in our software actually solves a problem for you and what doesn't? Obviously they want to keep some bundles just to kinda upsell you or whatever, But

Okay, sure, but if we're imagining what's the best optimal future here, It's like as things get more and more algorithmically decided, you probably have scenarios where you can have custom bundles, too, Where it's like, well, I'm gonna make this exactly to what you need, because now I have the time to just like have AI whip up a custom pricing solution for you. And that way you're maximizing the economic pie, if you think like on the demand chart of like a from econ class, like you're you're hitting the curve, if you will. Yeah.

Yeah. I think the interesting parallel to draw is, in consumer purchasing decisions, there's agentic commerce and people are focusing more and more on GEO as a channel there, as well as having the agents doing the checkout for you. Obviously, like nine-nine percent of those are more simple than your like average business decision, which is why those can happen. But I do think there's gonna be a lot of buyer enablement or buyer support where, you know, maybe that we even have AI buyers in the future that know exactly what your preferences are, seek things out on your behalf and save you time. Yeah,

I think a lot of people are betting on that.

yeah, to, make sure you can actually get what you want to solve your problem and get the best solution. No longer do you have to rely on, just random reviews online or just like your red threads and say, yeah, this is the best. Or, G2 has been like, or a lot of these other review sites, th you can't really trust them these days because everyone has four point seven stars plus, right?

Yeah, four point seven just means nothing to me effectively. I have no idea.

Yeah, you need to have it, but it doesn't really mean much, right? Yeah. But having your personal, procurement agent go out and find what's the best fit for your company at this specific point in time is what might be a game changer.

And then what are we saying that that agent's talking to a human on the other side, do you think?

Well, it's already happening, Muse and Instinct. They're already calling up people. Obviously, I don't know how well it's working, but I think that will be the even more frictionless future. And you know, maybe the businesses will realize, we don't want our sales reps talking to AI all day. We'll have like AI staff, so it's like AI to AI. Or maybe that's the wrong primitive here, and maybe it's like an MCP or some other sort of n document solution

That's interesting. I'm in agreement that customized solutions are going to be where humans are still going to be more involved, or like specifically solutions where it's not a commoditized result. You know? I think like a great example from a consumer standpoint is like a house. I d I don't think as a person I would be very comfortable trusting an AI to go and sell me a house. And it that goes back to that trust component because I don't want to go into the house and find out that there's actually a bunch of mold in the air conditioning units And the AI isn't gonna feel bad about lying and telling me that it's fine or just like glossing over that. But like a human hopefully has some compassion there. Right. And so I think like for those important purchases and those ones where it's like each one like each house is unique, That's kind of cool. and that's a scenario where that's probably still very prime for a human to be the seller. And even if you think about the softwares, It's those more complicated usually B2B softwares where it's not a commoditized product where you're you're shopping based on price, but you're actually shopping based on capabilities as well. 'Cause that's where you can start saying, Hey, well for my specific needs, where does this fit in the different solutions that I'm evaluating? Yeah.

Makes sense. Well, we've been talking a lot about the future. I kinda wanna bring it back to the present, make something a little bit more applicable. I'm curious to hear if you have any contrary on or hot takes around the current state of s enterprise sales maybe.

this is what I always ask folks. So it's you flipped it on me. It's it's scary. Yeah. my contrarian take is that I think that everyone takes for granted that sales cycles need to be 10 months long for enterprise. I think that's frankly ridiculous. Yeah. Right? With AI now, especially for software purchases. By the time 10 months has passed, like the difference in 10 months is like we started off with like 4.0 mini or like 4.0. Yeah. And then suddenly like now we're ripping open is 4.5 or whatever, right? And that was like game changing. Right. And like with software, the capabilities that come because of AI, 10 months, it'll be completely different, probably a lot better. And what you were making that purchasing decision for 10 months. Ago is is completely changed. So I think that as an economy, there is no reason that we should be having to wait so long to make these decisions, especially when they are probably important things. the software is important to be able to actually enable an enterprise to deliver the value that it needs to as quickly as possible. And so if you're s dead set on buying a software solution for a specific problem. That should be the priority. Mm-hmm. And you should do that as quickly as possible. Or otherwise, it's not your priority and just do that later. Yeah. Right?

Yeah. I think it's interesting because obviously there's a human aspect of politics and, having to get enough data to make a decision. But I think a lot of these things around alignment of what people are trying to do and even getting data within your own org are becoming faster and faster now because people, one realize we have to make a decision on AI where there's a lot of mandates out right now to, upgrade our stack and become AI native as a company. Or people can just ask Claude, you know, like, Hey, crunch the numbers for us. What's actually adding up here? Where are we seeing this bottleneck within our company? Where where do we optimize? thinking from theory constraints perspective. So I think a lot of purchasing decisions are going to change. And as you said, right, it's like, let's say if I was an enterprise, buying GPT-5, 10 months ago, and that was like, I need to spend 10 months thinking about that. And you finally got it now, and then but like everyone's on like fable like 5.5, right? Exactly.

Yeah, right, different vendor. Exactly. Right. I think that's what what it really comes down to. It's that certain vendors can move so fast now where you're an enterprise and you're looking at a vendor who's got another competitor and they're just like clearly the better one, but by ten months, that's completely changed. That's where it's so bizarre to me that these cycles take so long and I get why they have taken so long. But I think that that needs to change. I think that I think we can get it down to one month.

wow.

I think it's possible. I think it's a societal change that needs to happen.

Makes sense. Cool. Well, this has been a great episode, Alex. really appreciate you taking the time. I think we learned a lot here just on future takes, how we speed up the the present to go into the future and what founders can take away to achieve founder led sales. So thanks again.

Yeah, thanks for coming on too, Jason. Jason's gonna be on some more podcasts coming up soon, so everybody you should get excited about that.