
SaaStock Founder and CEO Alex Theuma speaks with Manny Medina, Co-founder and CEO of Paid (and former Founder and CEO of Outreach), about how AI is reshaping SaaS monetisation and the future of work. Manny shares his journey from scaling Outreach to $250M ARR to launching Paid, an AI-native platform built to help SaaS businesses move beyond seat-based pricing models. He explains why legacy systems are holding founders back, how to stay truly customer-obsessed, and why over half of every org chart could soon be filled by AI agents. Tune in to hear more about:: - Building a new monetisation stack for the AI era. - Why “seat-based pricing” is becoming obsolete. - The importance of in-person customer relationships. - Avoiding operational debt as you scale from startup to $100M+ ARR. Guest links: LinkedIn - https://www.linkedin.com/in/medinism/ Website - https://paid.ai/
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Culture is what you live every day. It's the actions that you take and the actions that you don't take. And by doing the things that we say we're going to do, as opposed to calling them out and putting them on document or on the wall, that's how you instill culture.
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Welcome to the SaaS Revolution Show, a podcast by SaaS Doc. Here we interview SaaS founders from around the world who've been there and done that as they share the ins and outs of how they built their businesses, their operations, their path to securing investment and more. Our mission with the podcast is to help you, the founder, learn how to scale your SaaS, maintain your wellbeing and navigate the complexities of this ever changing industry. I'm your host, Alex Deemer and together we'll explore the good, the bad and the ugly in the journey to SaaS success. SaaS stock Europe is next week. This is your final chance to join 4,500 AI and SaaS founders, leaders and investors in Dublin for two days. That will move your business forward. This isn't just another conference. This is where machine learning meets go to market, where funding meets future, where AI meets ARR. Network with the industry's most influential minds and learn from founders shaping the future of SaaS and AI. Big deals, real AI insights. Dublin Energy Limited tickets remaining, so be quick, book now at saasdoc-europe.com tickets. Welcome back to the SaaS Revolution Show. I am your host, Alex Steamer, CEO founder of SAS Stock, also general partner of Back Future Ventures. Delighted to be joined today by Manny Medina, who's the co, founder and CEO of, of paid. Or you say paid. AI or paid, Manny.
A
I, I call it paid paid. It's about, it's about getting paid.
B
Yeah.
A
And the, that AI will eventually just subsume in the. Because we're going to get more traffic as we grow.
B
Yeah, very good, very good. Well, it's fresh. We were together last night, but it wasn't, it wasn't just me and you. We brought the London sasdoc local community together. Thank you for obviously joining us. It was a great gathering, you know, around sort of 50, 60 SaaS builders, AI builders there. We got a bit of a sneak peek into what you'll be discussing at Sassock Europe as you'll be joining us at. Now you're a honorary European or honorary Londoner. You've got a short hop to come over to Dublin in a couple of weeks time, I think the 14th and 15th of October. So that was really helpful Also going to be helpful for the conversation today. And I, I know like a lot of people do know you Manny for, for Outreach, right? You, you, you co founded, you were the CEO of outreach. You, you know, grew that to over 250 million and were there for 11 years. But you're, you're going again. You're, you're, you're building paid, you want people to get paid. SAS companies to get paid, AI companies get paid. And also yesterday there was the announcement of your 21 million dollar seed round. And so you've done pre seed and seed in the space of like, I don't know, seven months. So some fast sort of growth and plans there. So we'd love to focus a little bit or more around paid, around AI. Why are you building this? Like, why have you decided to, you know, build paid, focus on this as the next big thing.
A
A couple of things, Alex was the first one is the fact that I experienced this pain of being a SaaS company as a leader of a SaaS company myself and seeing the fact that agents were only moving in one direction and that, you know, we, at average, we had been investing with AI for a long time. But the moment, you know, LLMs came to the, to the scene, everything changed in a very significant way. So, but what didn't change is your back office and your monetization stack and the ability to track costs and your ability to build a business on the back of this new technology. And you know, I'm a big and firm believer that you should always build what brings you alpha. You should not build things that, that are not going to differentiate you in the marketplace. So I'm sitting there at Outreach with, after a conversation that I had with Alan, the CEO of DocuSign, who was asking me, okay, so how many fewer seats do I need next year now that you have agents to hit, to hit my growth numbers? And it was a great question. A and B, I'm looking at a contraction event because he's not going to need as many seats if agents are going to take up some of the work. So, you know, I went to talk to, you know, my systems teams and I realized that our systems cannot support all the various ways in which agents deliver value. So an agent could be an AI sdr, which is out in the market. Well understood. But an agent can be a compete agent, an agent can be a manager agent, an agent can be a renewals agent, an agent could be an expansion agent. An agent can be a new product introduction agent. An agent could be an agent that sells in a particular market or demographic or industry that you need help in. So the ability for you to so like micro strategize what an agent can do is only a matter of like, you know, the prompt and the data that you have available. But the systems for me to go in charge for it were just obsolete. And you know, I was, you know, we're a Zora salesforce, netsuite stack, and none of them have been touched for over 20 years. And none of them were built in a time of agents. Matter of fact, like the common term in a SaaS world and even in the pricing world is a skew. Just think about a skew. It's a stock unit, it's a chair, it's a microphone. Like, why, why does that belong in software? Like, it's just nonsense to me. So when you look at what an agent does, an agent is providing all these services. An agent is performing all these activities, providing you a service and giving you two things. One is a set of outputs and outcomes that you care about, that you're paying, that you should be paying for. And two is, you know, preventing you, or like, you know, in this case, relieving you from hiring to have another human being to do the same work. Right. And that concept was just not understood and brought in into the picture. So to answer your question, why did I go start this is because that problem just kept bugging me. Starting companies is a very irrational thing. People don't do it for a lifestyle, right? People don't do it to live the Silicon Valley life. They do it because they have a problem that they are very personally involved in solving and they really want to solve the problem. I really wanted to solve that problem not only for outreach, but for all the SaaS companies out there that need to move to agents because seats are going down. So I feel like if I don't solve that problem, you know, in the position that I'm in, with the knowledge that I have, with the superpowers that I've acquired for the last 12 years, you know, I will be wasting, you know, a good chance and an opportunity for me to really change the world.
B
Would you assume that the zoras, chargebees, all the other like billing platforms will also need to start to solve this problem, but they're going to have a lot of legacy tech debt and not necessarily be like AI native at its core, and so it's just going to be harder for them to rebuild, to get there. How do you view that with where you are and just building this from the Ground up with AI at its core.
A
The fastest way to lose a race is to look back at the people you're leaving behind because that actually slows the body down. So I don't know what they're going to do and what they should be doing, but I can tell you from experience is that when you're running a few hundred million dollar company, repositioning yourself as something you are not is really hard, right, because people buy you for a particular set of reasons that you're known for and the things that you're not known for, you have to go and disrupt yourselves. So I think it's gotta be really hard from a positioning and messaging perspective to begin with. But second of all, because the technology is significantly different. So the way that we solve the problem for the agents is that we actually see everything the agent is doing for us to be able to figure out what you should charge for and what should you be given away for free and show the customer the work that you did. And that is not something that can easily be done through third party systems right now. The third party system right now live in this sort of like this configuration world where you sort of like tell them who bought what and what entitlements they have and they will sort of like give you the pricing back and you need all these people around it like you know, deal desk and finance and approvals and blah blah blah, blah blah, which is in this day of AI like it's just nonsense. So you know, we are, we are Reimagining the whole monetization 3 Infrastructure from the ground up, built purposely for agents.
B
Is it, is it your view that traditional seed based pricing is going to be extinct? And you know, in what period of time, if so.
A
So I put up a bold claim that I actually lifted from a few others that in five years we're going to see half the org chart being occupies by AI agents. So we're going to be moving to a world where you're not going to be hiring new humans into the, into the organization, but you're going to be hiring agents. And then the question is how do you pay them? Where do they belong? Who is their boss? How do you onboard them? How do you afford him? What is their, you know, what is security clearance an agent should have? What access to information should they have, how you observe them, how do you monitor the behavior, how do you even performance reviews to the vendors or the people who create the agents. So we are going to live in a world where the agents are going to be very Much tied into the fabric of the corporate culture and the corporate and the corpus of the organizations.
B
Is your initial focus in ICP positioned around SaaS companies to help them with this new model of pricing? Or are you also, and how would you I guess differentiate the AI native like SaaS startups which are really, really B2B software, but they've just got AI at their core, you know, would you say one you're focusing on rather than the other or both?
A
So I would, I would. The analogy that I will give you is you, I have this, this hose of water and I was, I began irrigating the garden of all the different SaaS, all the different AI agent startups that were coming out of the ground and they were, they needed this infrastructure for them to scale and that was my primer, icp. And then I realized that not too far away there was a massive fire in a building with people in it that needed to be rescued and I'm the only one with a hose. So now I have to do both. I have to continue to irrigate my market. But if I don't save those who are in SaaS right now, who are charging per se in a world of declining seats, unemployment by the way in the junior roles is up 13%. So seats are not being added to organizations. If anything else, every organization that I know is cutting seats as they're growing, which is operationally impressive, but it's bad in general for SaaS companies who are selling against those human beings in seats. So if I don't help solve that problem right now, there's going to be a lot of bad news and I'm trying to prevent those bad news. So I'm running as quickly as I can with this hose. So to try to douse a fire that is happening in the SaaS world that haven't changed their pricing from seats to agent based pricing, would you say.
B
SaaS is in a kind of like existential sort of like moment that if they don't become AI first AI native and you know very soon that yeah, it's just going to be critical for a large number of companies, right?
A
100%. And some of them are realizing, and some of them are not realizing that they're sitting on a burning platform?
B
Hard to say. But do you think like the term SaaS is still like, are we going to be using that in the near future or in a couple of years time? Are we just going to be saying these are AI startups, like AI software companies?
A
I don't know. That's A great question because I actually think that SaaS maybe run into extension too. And there's, and it's for a different reason in that first of all, most, most software right now is consumed as a service, or I would say most, but a large quantity of software is consumed as a service. So that in itself is not a. You know, when you say software, you assume SaaS, you see, I mean you assume that the delivery method of that software is going to be via the Internet. So I don't know that SAS makes sense anymore as a, as a, as a, as a nomer to define what you are. The second piece is that because of the balkanization of the. Of personal data, because of the vulcanization of the of of of hyperscalers and what each and the, and the sort of like the imperative at the national level of owning your LLM to your infrastructure and your compute, we're going to see a lot more regional clouds and we're going to see more custom deployments that are going to be looking like more on premises. And now that we have containers and many other artifacts to be able to deploy on prem and hardware is cheap, I don't know that SaaS actually gets there like when we assign a deal with a company called ifs and a lot of their deployments are in parts of the world where your delivery method as a service is kind of poorly defined in an oil rig. You're not hooked up to the Internet now that we've starlink. Maybe you are. But like your, your systems are not, you know, constantly being updated and refreshed. So you need different policies to update those systems and you need different, different strategies to be able to get to those remote locations. So I don't know that SaaS is going to be as a term alive for very long. I think we're gonna come up with something new and agents feels like the, the, the right direction in general.
B
And you, you've been building pay since early this year, right. I guess kind of officially kicks off this year. What are you doing differently that, that you did, I guess kind of outreach and then also I guess during that point to, to get to the traction of where you're at. I think maybe you shared yesterday you're at around a million ARR or something like that. And which is, you know, helped you with the, with the seed round. But so I guess what have you been doing differently and you, you know, what's been working for you to get traction for pay. Yeah.
A
So let me start with what I'm doing the same. So in terms of outreach, what I'm doing the same is we're selling right away. We're selling ahead of capability. We're selling and we're getting, you know, we're, we're getting our feedback on our product direction directly. For somebody who would pay us money for the product, that is very helpful. We're also very customer obsessed. So we make sure that we stay on top of the customer. We take a look at what the customers are doing every day to make sure that we have an understanding of, you know, what kind of value they're getting from the product. What I we're doing differently is it's pretty much everything else. So you know, outreach of my first company, so I didn't have a good notion of what building a company looked like. So I took a lot of advice from VCs that in retrospect was bad advice and I don't think I will ever do that again. So number one is that the most important thing is not the code or the engineer or anybody here in particular. The most important thing is the customer. And as long as we are wrapped around the customer and what the customer problems are, understanding the true needs and we're constantly solving that problem with alacrity, with panache, with good taste and with urgency, we're going to be okay. So this customer obsession is something we had at outreach, but here we bring it to the nth degree in that every single one of our engineers gets forward deployed as a part of their onboarding, as a part of their onboarding, just as part of their life. And forward deploy means that here it means truly what it means, which is we will work in our customers code. When we sign a deal with somebody, we tell them, okay, so as part of this paid money that you pay me, you're going to give access to this person that is going to sign an agreement with you that he's going to come in as a contractor, the operator is going to fork your code, he's going to install the work, he's going to make sure that you are set to success and then we're going to, and then we're going to PR it. And you know, a lot of people find that a little weird but for us it's critical that we are working in our customers code base so that we understand the problems at the rawest, most primitive level. Not in the way they're telling us the problem is, but in a way that we observing the problem is in their code base. And when I built outreach that you know, that was not Possible for a number of reasons. One, like the most precious thing was the developer. You have to respect everything they were doing and like their, their time being hits down in the zone was, was the most precious thing. And, and, and right now we, we don't like our most precious thing as a customer. And if that's going to set back our product roadmap and execution, then so, so be it. We'll, we'll work a little harder, work a little longer, work a few weekends and we'll get our line. So things like that are completely different for us.
B
Yeah, on the, on that. So you shared that sort of yesterday in terms of, around sort of culture, the obsession on customer and I don't know if you would use the word obsession, but you know, the, the culture around winning and like, how do you view that? How do you hire for it? How do you install like, you know, a culture of winning within a business?
A
I think it starts, you know, culture is developed in sort of concentric circles. So you know, the, the, the original team of, of the co founders and the founding engineers, you know, we, we acted that way from day one. So when we are acting that way from day one, meaning you are going to your customer's, you know, code, you're doing the deployments yourself. Like Raj flew out to meet with Happy Road and he lived in their offices for a week to make sure that it got done. When that is what you do, then the other people who join you and do the same, then they start adapting to that culture. Then you start wondering, why is that? We do it. Oh, we do it because customers are the most important thing. Oh, we do it because we can learn that way faster. As opposed to like hearing customers feedback or putting on a spreadsheet. No, you go and work in the customer's shoes. So culture is what you live every day. It's the actions that you take and the actions that you don't take. And by doing the things that we say we're going to do, as opposed to calling them out and putting them on a document or on the wall, that's how you instill culture you had.
B
With outreach as you, I think cross 1 million or maybe it was before, but you had this, I don't call it like a motto or something. You were trying to instill 10 million or die tmod. Is that something that you're bringing into to paid as you look forward to 10 million? How do you view that? Is it something different?
A
We're a different company and I want to honor and acknowledge that. That was awesome that we did at Outreach. And other people like the founder, hey Reach, he copied tmod or like the founder of, I forget this other company, he copied Timo too. And I think it's kind of awesome that you do that. We're going to do here whatever is going to work for us. I'm not, you know, I'm trying to bring, I'm trying to be light on the artifacts that I create at Outreach because this is, this is paid. Paid is built by different people. Paid is in London. Paid has a different vibe. Paid, paid is just different. So. So I don't know, I don't know the answer to your question, but I'm sure we'll come up with something cool.
B
Is it, is it easy or hard? Then like given obviously you have this like 11 year experience, you know, kind of with Outreach to say, okay, I did that here, but this is a new company. Just you know, think, thinking back to like the past and the things that you did to try and say actually no, it's a different company, let's not do that. You know, let's think of something different, think of something new as a new business. Like do you ever, you know, are you thinking about that? Like whether it's a lot or during, you know, during your day to day.
A
No, I worry about the customer. No, I want to make sure that we're addressing customers needs that I worry about different things. Like I worry about things I didn't worry about. Average. For instance, yesterday I showed this chart that I think that you remember that I wasn't plotting revenue growth, I was plotting acv. And I think like that's one of the things that most people miss is that revenue growth. Anybody can every, anybody can flex revenue. I can hire five reps right now and, and hit a million dollars in a very short period of time. Like this is not the hard thing to do. The hard thing to do is get high quality revenue that sticks, that is scalable after 25, 30, 50, 100 million. And, and that what I said yesterday is that you have to figure out what is your optimal ACV for the product you're delivering and the problem that you're solving and then operate at that efficient frontier. If you don't find that out early, then you're suboptimal and then you decide to scale revenue. And guess what? The moment you raise a series A or a series B, that VC is going to come super stoked over your revenue growth and he will want to see points on the board on the regular and now you're forced to put points on the board in a really bad way, in a way that doesn't really scale after a particular number. So, you know, I seen that movie before. Like, the average was 2 to 10, 10 to 25, 25 to 50, 50 to 100, 100 to 190 or 180 something and then 180 something to 200 and something and then 200 something, 250. So that's a very fast clip of growth. But if I were to redo it all over again, I would optimize for what ACV I'm solving for, slowly work up to it and then scale fast. I mean, and that's what we're doing here. I'm tracking ACV like a hawk to make sure that we're getting that when we scale, we're going to scale an efficient operation. It's not going to be sugar revenue. It's going to be all, you know, good macros and proteins and stuff.
B
What, what are some of the, let's say, challenges or like just, just with the, the current AI era that we're living in, this, you know, the state of the market that, that you see ahead, you know, for startups of whether it's yourself but, you know, of your size and that you're looking at and thinking often, you know, dealing with, trying to overcome.
A
I, I think I, I see nothing but opportunity. I don't see any challenges. I think that the, the, the world is richer and more meaningful and, you know, with a lot more possibilities than ever was. It's just, you know, how do you, it's your, is the mindset that you put to it. Like, do you, you can frame it as a challenge, you can frame it as an opportunity. For me, it's all opportunities and, and I'm, I'm extremely grateful to be surrounded by this group of individuals here in the office that, you know, relish that opportunity, that see it as a challenge and deal with it with curiosity and, and urgency. So, for instance, when I was at Outreach, you know, rebuilding code was a huge deal that required many, many meetings and a lot of feelings hurt and like, what are we going to do about this? You know, we're going to have to rewrite it. Technology here moves like every new, every other month or something new. And it's your duty to offer to your customers the best solution for their problem. Our duty. So if we have to rewrite code, so be it. Who cares? Nobody dies. Your customer, you keep your customer. So like, every day we have to walk Wake up and walk into the office and earn our customers trust and love. You see, I mean, like, that is a very privileged position to be in. And as long as we continue to execute that way, we're going to be okay.
B
Where are you on the. Because given this is the second time, you perhaps didn't need to do this. Right, but you're doing it. You saw the problem, you wanted to solve for this. But where, where are you in terms of, let's say, like work life balance and you know, the, the amount of effort that you put into the business? Obviously there's a lot of talk around 996 sort of culture. I read something by Howard Lerman, who's building Rome now after he did sort of like yext and you know, in terms of like, what, what he's doing, you know, where are you on this sort of scale?
A
But you know, what was so funny about that tweet? Nowhere in that tweet he talk about his customers.
B
Yeah, nowhere.
A
And I love Howard. He's a, he's a good dude. But, you know, it was all about his fitness and the fact that his calendar was empty and open and ready for whatever. Like, if I am him, I will have his calendar chock full of conversation with his customers. So look, it doesn't matter like how you schedule your day. This is all nonsense that is brought in by the VCs who have nothing else to do. Like, we should talk about how do you win at the cost at the point of the customer? How do you retain those customers? How do you grow your acv? How do you scale your teams? Like, those are the meaningful conversations. All the rest of the stuff is noise.
B
What about then in terms of then like how many customer conversations are you, you know, having?
A
You know, I have a steady diet of five a day.
B
Five a day. Are they mostly. Do you see this? You know, are these like online meetings? Given that customers may be geographically dispersed, how do you balance and view in person customer relationships? And look at that from a schedule versus doing online meetings. Because with our business, you know, for instance, and if we talk about like our ACV, it's under 50k, right? And say a battle that I've had seems to be sort of like losing is trying to get, you know, my sales reps out to visit customers. But we have a lot of, you know, customers in the US and not necessarily saying it's an excuse, but people have spread all over, you know, the team is in London, their customers are used to doing business, you know, on Google Meets and you know, being efficient and just kind of finding, finding that balance. And so for me it's been like, I love to go visit the customers. It's hard to scale, it's not as efficient. But when you have that in person customer meeting, build that relationship, it's often so much more impactful. Right. But conscious of or curious to your view and how you manage that and balance it.
A
I try to have as many in person conversations as I possibly can. So that's where London is both a blessing and a curse in that London makes it very accessible to be somewhat central to all time zones. But my customer concentration is in the west coast of the U.S. and, and traveling is, you know, as you can imagine, is very far. For the customers I do have here in London, I meet, I meet with them in person. You know, I haven't come to our office, we go to their office. I think customer in person meetings are the most valuable thing that you can do. And we were even talking about that for our four deploys that we did a couple in person and they were significantly higher value post deployment to, you know, work their problems than when you were, you know, just online all the time. I'm trying to think the majority. Yeah, so we, we tried to make the majority of the meetings in person. It turns out like for the customer sometimes it's difficult. But what I do try to do is after the deal is closed is go meet them in person for sure. So like you as a CEO should make that 100% of a priority to go meet customers.
B
What about just sort of switching gears a little bit in terms of your own use of AI as a CEO on a day to day basis? Like what are a couple of tools that you're using? How's it helped you be more productive, more effective?
A
So I, I use, you know, Gro chatgpt and, and, and Claude as a thinking partner and I, I gave the same problem usually to all three of them. So you know, when we're thinking about strategies, we're thinking about go to market, we're thinking about approaches, we're thinking about, you know, our own pricing and packaging, our own scale ups, things of that nature. So and, but I don't use them to just compose documents, I use them. Aspiring thinking partners. I love to talk to, give myself notations. So I use a lot of whisper flow, I love that product. I use a lot of granola of course and we send the summaries around quite a bit. We actually have granola on all the time even in the office. So that if we impromptu just get up and chat with each other. Granola is still recording so that we're able to summarize some of the stuff that we said. Those are my main tools of the trade at home. I use Perplexity. I don't go to Google. Go to Perplexity for any questions. What else did I use that has AI embedded in it? I don't know. I'll come up with something else, but that's a majority of it.
B
And as we look ahead, like in less than two weeks, you're going to be to Dublin. Have you been to Dublin before?
A
I haven't. That's a great question. Most people don't ask me that question. I haven't been to the.
B
Okay. First. First time. Well, hopefully I'm sure you'll love it. It's a great city, great people. You know, the city should come alive somewhat with, with Sastock in town, so more founders and builders and our people there. So it will be great. I'll send you some tips and maybe things to do depending on how much time that you.
A
I heard that you have a secret, a secret list of, of the, the funnest bars.
B
So I, I do, I do.
A
I'm really, I'm really excited about it.
B
I'll. I'll try and make, make the time myself to, to attend them, but it's difficult when you're running the event itself. What will you be speaking about at Sassock? This, this will be your first Sastock Europe, uh, event. What will you be speaking about? Who are you looking forward to, uh, to meet, uh, whilst you're there?
A
So I'll be giving the same presentation that I gave to your crew yesterday. So it was great to get the feedback. It was great to sort of like iron out the chinks, the kinks rather of the presentation. So, yeah, if you have any feedback about what worked and what didn't work, what to do more, what to do less, please send it along. So it's going to be the same about my journey at average and I focus mostly on the 0 to 100 because that's the hardest part and that is where the majority of the mistakes were made. SaaS is kind of weird in that you have to really be very careful with initial conditions because when, when it does work out so many times it doesn't work out right and you stall and you're small and then that's it. Then it doesn't matter. But, but when it does work out, if you don't pay attention to the initial conditions, you will have to you. You walk yourself into a world of hurt that you didn't need to. And one of the things that I didn't speak enough about is about the operational debt that you incur when you're small. That doesn't go away. And I think it was the founder of Rippling who said it best that operational debt doesn't go away as you scale, it just becomes harder to solve. So things like product debt or customer support debt or HR debt or things that you decided to skip and throw people at it, you hit your 10 and then even triple, triple, double, double doesn't work anymore. So you hit your 10 and now you're going to 50 and you focus just on getting to that 50 that you forego. All the other stuff that is good for when you hit 50 and you get now to get to a hundred, you know what I mean? Like your ACV and your retention policies and that your contracts are tight and that your, you know, your post sale motion is tight, that your upsell motion is tight. All those things are hard to fix when you have a gun to your head to go and out execute what you used it last year. So that's a sort of like, what's the word I'm looking for? That's the gospel that I bring to the masses. It's like, look guys, like I did it to 250. Don't be me. You know, try to be a better me and like try to fix all your go to market and operational debt issues early and culture issues early so that you know, when they scale they don't bite you in the ass.
B
Awesome. Well, I have seen the sneak peek of the talk, but I'll be there again and obviously we'll have a bigger audience for you to share that gospel with in Dublin at SASDOC Europe coming soon. So really looking forward to that and your first time in Dublin and at the SASdocs at the main conference. So really appreciate that. Manny, for those that maybe are not making it out to Dublin, where can they find out more about Paid if they're sort of curious to find out more.
A
Yeah. So go to paid AI and just follow me on LinkedIn. Manny Medina. We put out a lot of content, both paid and myself. We put a lot of content. We have a podcast called Get Paid. So you can see behind me, it's Get Paid. You can subscribe to that podcast. There's a lot of good content around monetizing agents and people building companies. I realized that when I started Pay that there was no there was no show anymore about about building in the era of agentic, like what's different, what's new? And about the building itself as opposed to the victory lapse of like, you know, I hit $100 million in 15 days, like, whatever. Like, I want to make sure that people understand that building is still hard and that this is a craft and very, very, you know, many are called but few are chosen. So this is for all that are called and want to be chosen.
B
Awesome. Well, I didn't know you had a podcast, so I'll subscribe to that. Always looking for new shows that are relevant. But Manny, thank you so much for being a great guest on the on the podcast today. We'll see you at SAASDOC Europe in two weeks time.
A
Look forward to it.
B
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Episode: From Outreach to Paid: Manny Medina on AI Agents, SaaS Monetisation, and Building for the Future
Host: Alex Theuma
Guest: Manny Medina, Co-founder & CEO of Paid.ai
Date: October 9, 2025
In this engaging episode, Alex Theuma interviews Manny Medina, the influential co-founder and CEO of Paid.ai and previously Outreach. They dive deep into the paradigm shift from traditional SaaS seat-based models to an AI agent-powered world. Medina discusses why the current back-office infrastructure is inadequate, how agent-based monetisation works, concrete strategies for building a company differently the second time around, and his vision for the future of SaaS (and maybe the end of the “SaaS” label itself). The discussion is rich with practical advice, anecdotes, and a clear urgency to adapt to the AI-first era.
"The systems for me to go in charge for it were just obsolete... None of them were built in a time of agents."
(Manny Medina, 06:06)
"We actually see everything the agent is doing for us to be able to figure out what you should charge for and what should you be giving away for free."
(Manny Medina, 08:08)
"In five years we’re going to see half the org chart being occupied by AI agents."
(Manny Medina, 09:20)
"I actually think SaaS may run into extinction too."
(Manny Medina, 12:34)
"Every single one of our engineers gets forward deployed as a part of their onboarding... so that we understand the problems at the rawest, most primitive level."
(Manny Medina, 15:37)
"Culture is what you live every day. It's the actions that you take and the actions that you don't take... That's how you instill culture."
(Manny Medina, 18:04 & 00:02)
"Anybody can flex revenue... The hard thing to do is get high-quality revenue that sticks, that is scalable after 25, 30, 50, 100 million."
(Manny Medina, 21:04)
"We should talk about how do you win at the point of the customer... all the rest of the stuff is noise."
(Manny Medina, 25:00)
"Customer in person meetings are the most valuable thing that you can do... you as a CEO should make that 100% of a priority to go meet customers."
(Manny Medina, 27:35)
"Operational debt doesn't go away as you scale, it just becomes harder to solve."
(Manny Medina, 31:30)
"Starting companies is a very irrational thing. People don’t do it for a lifestyle… they do it because they have a problem that they are very personally involved in solving and they really want to solve the problem."
(Manny Medina, 06:48)
"We're selling right away. We're selling ahead of capability. We're getting our feedback on our product direction directly from somebody who would pay us money."
(Manny Medina, 14:57)
"By doing the things that we say we’re going to do, as opposed to calling them out and putting them on a document or on the wall, that’s how you instill culture."
(Manny Medina, 00:02 & 18:04)
"All this is nonsense that is brought in by the VCs who have nothing else to do."
(Manny Medina, 25:00)
"It’s not gonna be sugar revenue. It’s going to be all, you know, good macros and proteins and stuff."
(Manny Medina, 22:13)
Manny Medina gives a masterclass in future-proofing SaaS businesses—insisting on relentless customer focus, abandoning now-obsolete seat-based pricing, and preparing for the agent economy where both monetisation logic and culture need a total rethink. Founders listening to this episode will walk away with a sense of urgency: adapt to agent-centric business models, rebuild back-office systems for tomorrow, and never lose sight of the customer amid hype, growth, and distractions.
Find out more about Paid:
Host Note:
Catch Manny Medina live at SaaStock Europe, and keep tuning in to the SaaS Revolution Show for more trailblazing SaaS founder insight.