Get Paid with Manny Medina

Are we in the iPhone moment of AI, or are we still building janky mobile apps? Box CEO Aaron Levie brings 15+ years of enterprise software experience to break down the biggest questions facing SaaS companies today. From pricing models to regulatory risks, this conversation goes deep on what's actually happening behind the AI hype.The Great AI Pricing ExperimentEvery software company is scrambling to figure out how to monetize AI agents. Do you charge by seats, tokens, outcomes, or some hybrid model? Levie reveals the chaos happening in boardrooms:"There's no board of directors in software that is not making this the number one topic of every board meeting."The challenge isn't just technical - it's existential. Companies are making architecture decisions in a vacuum, and there's a high probability many will get it wrong.Why AI Layoffs Could Backfire SpectacularlyHere's where things get controversial. Levie warns that tech leaders using AI as cover for regular performance management are setting the industry up for regulatory disaster:"People like Bernie Sanders will then totally jump on that. And so we as an industry are doing ourselves a disservice when we kind of over prop up that message because that's actually the surest path to over regulation of this technology."The Productivity Paradox: Why AI Made Box Hire MORE EngineersForget the cost-cutting narrative. Levie shares how Box's AI implementation led to hiring more people, not fewer:"If we can accelerate our product roadmap, that actually encourages us to hire even more engineers, because now we have higher productivity in this part of the organization to deliver even more value."The key insight? Companies focused on output expansion rather than cost reduction will dominate their markets.The Oracle Reality CheckIn a moment of refreshing honesty, Levie admits his past predictions about "obvious" disruptions were dead wrong:"You live long enough to see Oracle as a $600 billion company. When you're naive, you would have said, well, everything's obviously moving to SaaS and this business is going to get totally disrupted. You're constantly reminded that Larry Ellison's the G.O.A.T."This humility shapes his contrarian take on AI disruption.Will AI Kill Salesforce? The Surprising AnswerLevie's boldest prediction: traditional SaaS platforms will coexist with AI rather than be replaced by it. He compares it to how movies and TV coexisted rather than one killing the other:"I look forward to replaying this in 10 years and it might be so laughably wrong, but just think about other paradigms, right? When movies came out, when TV came out, it coexisted with movies."The Architecture That Matters: Church and StateOn the technical side, Levie argues for strict separation between AI agents and core business data:"I think you really do need to have a separation of duty or a church and state between what the agent is doing and the underlying object model, data model, or kind of business process."The risk? Non-deterministic AI systems corrupting your deterministic business data.The Final Word on AI StrategyLevie's closing advice cuts through the noise:"Everybody should be thinking about AI agents for expanding the capability of their software and their organization. And when you have that kind of prism in which you execute, you will find 10 times more interesting things to do than just replacing some kind of cost center."This episode is essential listening for anyone trying to understand how AI will actually reshape enterprise software - beyond the hype and fear-mongering.Companies Mentioned:BoxOracleSalesforceServiceNowWorkdayMicrosoftMetaDropboxDocuSignGleanCongaSnowflakeAirtableIntercomLinearAsanaAtlassianChatGPT/OpenAISee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

We sit down with Bryce Maddock, CEO of TaskUs (60,000+ employees, $1B+ revenue), who delivers the most honest take you'll hear about AI's impact on the service industry. As one of the world's largest BPOs navigating the AI transition, Bryce pulls no punches about automation claims, job displacement, and what's really happening behind the headlines.Bryce exposes the disconnect between public AI claims and private reality:"I see metrics where it's like, hey, We've automated 60, 70, 80% of our customer support. And I'm in the background being like, well, we still have the same number of humans. So I don't understand how those two things are possible."This isn't skepticism - it's insider knowledge from someone managing contracts with 200+ of the world's biggest tech companies. TaskUs is literally losing money on purpose to win the AI game:"Today your per contact price is $2, right? We'll give you an upfront savings. It means we're going to lose money, but we'll charge you $1.50. We'll charge you $1 a contact. We'll lose money for the first year."They're moving from the traditional "law firm model" where "lawyers were just very, very poorly paid" at $15-20/hour to outcome-based pricing that aligns with AI capabilities.When asked if all 60,000 employees will survive the AI transition:"I don't know that all 60,000 are going to make it through the journey. There certainly is going to be temporary dislocation where people are going to lose their jobs. And I think anyone who says differently is not being truthful and doesn't understand the power of this technology."Don’t underestimate this. Stop and listen - this level of honesty is rare from a public company CEO, but Bryce explains why sugarcoating serves no one. "The next phase is going to be even more impactful for my business and for all BPOs, is beginning to really become an agentic solution where things that took two, three, four, six weeks to train a human being to do, you can now train an agentic system to do. And I think that's where the rubber will meet the road."Bryce also reveals how media headlines drive bad business decisions: "What's actually happening inside our customers is that there's massive pressure from the board and the C-suite because they listen to podcasts like this or read the headline articles and it's like, hey, know, Klarna doesn't have any humans doing customer support anymore. Why do you?""And so it's very easy for that pressure to build and for the C-suite and the board to say, we need to see real change. In the middle of the business, there is a lot of fear."In another part, Bryce shares how VCs wouldn't fund TaskUs because it "wasn't techy enough" - and why he's now glad they stayed true to their service company roots while embracing AI partnerships. "The irony is this makes it harder for us, because a lot of the context that get escalated to humans become just really pissed off customers who want a human to yell at. [...] The agent can follow the policy and still piss off the customer such that they're like, I want to talk to a human being."Bryce explains how humans become "premium features":"Launch a white glove support line where if that customer contacts us, we can pick up the phone with a human being in five minutes and solve their problems. These human agents are much more empowered to actually solve problems.""Either I'll look like a genius or a complete fool in a few years. So I'll be excited to look back and see which it is."This episode offers unprecedented insight into how one of the world's largest service companies is navigating the AI transition, with brutal honesty about what's working, what's not, and what's coming next.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this conversation with Kellan Carter, General Partner at FUSE, listeners discover the seismic shifts in AI investing. Kellan reveals that traditional SaaS metrics are failing and stresses the importance of financial sustainability over vanity metrics. He argues that companies must adapt their strategies, moving from a 2010s sales model to a product-focused approach that emphasizes customer outcomes. The discussion highlights the challenges faced by both new startups and established firms in navigating the increasingly complex landscape of AI-driven markets.

Alexander Matthey, CTO and co-founder of Parloa, discusses the future of customer service through AI agents. He challenges the notion that automation will lead to unemployment, suggesting instead that people will actually prefer human interaction. The conversation touches on the necessity of agility in a rapidly evolving market and how specialized AI can enhance customer experiences. Matthey emphasizes building high-quality AI platforms, like crafting a "Ferrari," to stay competitive and effectively integrate technology while navigating industry hype.

We hosted Max Altschuler, founder of Sales Hacker and GTMfund in our studio to talk about how AI is fundamentally reshaping go-to-market strategies and why he thinks most GTM software companies are in trouble.After a near-death experience, Max made a radical life change - selling his dream home in Scottsdale and going "asset light" to prioritize nature and lifestyle over traditional success metrics. As he explains:"I really am just the happiest person when I'm in nature. I'm a better father, partner, friend, and I'm better at my job. Like I need to be in nature."Max's GTMfund has a unique model with 300 software executives as LPs, creating what he calls the ultimate sourcing engine. But he's avoiding investments in GTM software entirely, seeing a "cloudy, soupy layer" where even successful companies like Outreach face existential threats from their own efficiency gains."If you can get 20% more capacity out of your sales force... you just need to hire 20% less reps to get the same productivity."The conversation revealed several counterintuitive insights about building sales teams in the AI era. Max advocates for quality over quantity - hire "absolute killers" from companies like Outreach, support them with growth engineers, and focus on what he calls "hard as a moat" strategies."When only two emails came into that VP of sales saying 'congrats on the Series B,' it worked. Now when they get 600 emails, they mute all of them."Max is bullish on vertical software and global infrastructure plays, pointing to massive opportunities in untouched industries. His recent investment in air traffic control technology exemplifies his thesis - find industries with no innovation for decades, then back exceptional founders to transform them."Hard is a moat. Like it was hard for me to go uncover who raised the round and do the work. Now that that is like one click."Perhaps most interesting is Max's take on community-driven growth. Despite running Sales Hacker for years without cracking paid communities, he now sees them as more powerful than ever."Communities are stronger than ever... even if I don't make any money off my investment in the fund, I'm so happy I did this because of all the events and the community."He also warns about the dark side of AI in customer support, questioning whether companies like Klarna are moving too fast in replacing human teams."As a customer, I'm not really sure I want to hear that... I'm spending $100K with you for SaaS software versus like $15 on an Uber ride. Those are two different customer support experiences."What's emerging is a new playbook where "hard" becomes the ultimate competitive advantage, vertical markets offer the safest returns, and human relationships matter more than ever - even as AI automates everything else.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

We sat down with Adam Schoenfeld, co-founder and CEO of Keyplay, to explore how AI is transforming account selection and go-to-market strategies. Adam has taken his years of experience building Simply Measured and turned it into solving one of B2B's most persistent problems: figuring out which companies to actually sell to.While everyone else is trying to use AI to spam more people, Adam sees a different future. "The biggest trap that a lot of people are falling into is they're seeing this as kind of a volume game. The best people are gonna use it to create more value for a more targeted group of people."Keyplay's new AI agents are doing something remarkably different from traditional account scoring. Instead of just looking at firmographics like company size and industry, these agents can answer nuanced questions like "What's the security maturity of this company?" or "How do they prefer to buy software - legacy or modern?" As Adam points out, "A smart AE would take their territory and they go research these accounts. They really think about, like, what's the org dynamics? What's the kind of buying posture?"One of the most eye-opening parts of our conversation was about the hidden costs of bad targeting. Adam shared how companies are burning massive amounts on LinkedIn ads targeting companies that will never buy from them. "How much of that spend is actually going to accounts that are legitimately never going to buy from you?" he asks. Keyplay can identify and eliminate that waste while helping teams focus on higher-quality accounts.The pricing journey has been particularly interesting. They started with flat fees but quickly realized different use cases had vastly different complexities. "Some are super complicated and they're running across like a million records and some are very simple and they're running across 3000 records," Adam explains. This led them to adopt a credit-based model, though he admits "it does take some translation" to help customers understand the value.What's refreshing about Adam's approach is his candid admission that this is all a work in progress. When I asked about convincing RevOps leaders who might be threatened by AI reducing headcount, he had an interesting observation: "I don't feel like I'm having to convince people of that too hard... they want outcomes. They want to do creative work. They want to be the one who understands the customer and has great taste."Perhaps most valuable was Adam's masterclass on building an audience before building a product. Through his Pure Signal newsletter, he spent months researching go-to-market challenges and sharing insights, which ultimately led to discovering the problem Keyplay now solves. "I basically built like a mini media brand where people would subscribe to my newsletter... that led to discovering the problem that Keyplay solves now, because people would come in and they'd want to talk."Looking ahead, Adam sees a future where Keyplay could orchestrate entire go-to-market campaigns, from identifying the right accounts to actually placing the ads. "It would be incredible if we could just say, yeah, turn on Keyplay, we will each month rejigger the accounts you're targeting and we'll just deliver you pipeline."Whether you're in RevOps, sales, marketing, or building an AI company, this conversation offers crucial insights into how AI is reshaping B2B go-to-market strategies - not by doing more of the same, but by fundamentally rethinking how we identify and pursue the right customers.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this eye-opening episode of Get Paid, I spoke with Sahil Mansuri, founder and CEO of Bravado, about how AI is dramatically reshaping the landscape of sales and recruiting but not in the way most people think.While many SaaS companies are seeing their business models threatened by AI's ability to automate human work, Bravado is experiencing the opposite effect. As Sahil explains, "Because we were in recruiting and what we did was more services heavy than software heavy, venture capitalists used to be less excited about our business." However, the rise of AI has transformed Bravado's economics completely. "Now we're operating at an 85 to 90% software margin because AI has basically taken over and is doing 95% of the work that the human being was doing," he reveals.Bravado helps companies hire top-performing salespeople through their AI-powered recruiting tool called Hunter. What makes this particularly interesting is that while AI is automating many roles across industries, sales is one function that remains stubbornly human-dependent. As Sahil points out, "You can build AI engineers and AI marketers and AI doctors. But if you want that AI product to get adopted by Siemens, you're going to need a real life fleshy human being to fly to Germany, sit there and meet with 40 different executives."This creates a fascinating dynamic: as companies like Cursor, Anthropic, and others develop powerful AI tools that eliminate jobs in other departments, they're simultaneously building massive sales teams to sell those very products. The value of great salespeople isn't decreasing, it's increasing.Sahil shared several counterintuitive insights about hiring in today's market. Companies often make the mistake of hiring from big tech logos when scaling up, but "that person who joined Stripe when they were at a billion dollars and now took them to 1.4 or 5 billion is not the same person that's gonna take you from five to 100." Instead, Sahil recommends hiring people who are "overperforming at a shittier company than yours" because giving them better tools and resources will allow them to excel even more.Regarding the skills that matter most for sales professionals today, Sahil emphasized the growing importance of technical knowledge and genuine subject matter expertise. The days of "quarterbacking" a deal by bringing in specialists to handle the technical questions are over. Today's top AEs need to be able to answer complex questions themselves, especially when selling technical products.One of Sahil's most provocative claims is that prospecting is making a comeback. After years of relying on automated outreach tools, companies are rediscovering the value of personalized outbound like calling, relationship building, and social selling. "Once you get them into the door and you get them on the pitch, most people have a really tight funnel. Most good sales teams are able to close. The problem's always top of funnel," Sahil explains.Perhaps most controversial is Sahil's take on AI sales development representatives (AISDRs). While there's been significant hype around AI completely replacing SDRs, Sahil believes "that job is never going to exist" for high-value enterprise sales. "My very strong opinion is that as more and more companies build more and more automation and AI products, the demand for hiring more salespeople will go up. The compensation of sales professionals will go up."He points to companies like Slack, which initially prided themselves on having no salespeople, only to eventually get "crushed by Microsoft for not having enterprise salespeople." Even Jack Dorsey at Square recently acknowledged during an earnings call that they need more salespeople after realizing that their product-led approach wasn't enough.What's emerging is a new model where AI handles the mundane, repetitive tasks like data entry, scheduling, follow-ups - all while human salespeople focus on high-value activities like building relationships and solving complex problems. This shift is also happening in recruiting, where Hunter automates the tedious parts of the hiring process so that human recruiters can focus on closing top candidates and ensuring cultural fit.As businesses navigate this transition, Sahil believes companies will need to move away from per-seat pricing models toward outcome-based approaches that reflect the value created by AI. This aligns perfectly with our mission at Paid, as we help companies capture the true value of their AI-powered products and services.Whether you're building a sales team, developing AI products, or just trying to understand how technology is reshaping business, this conversation provides invaluable insights into the future of work in the age of AI.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In the latest episode of Get Paid, I had the pleasure of speaking with Jim Cutillo, a 30-year veteran of the mortgage industry and founder of Alpha7x. His company is transforming mortgage lending with AI agents that cut costs and streamline the entire process.If you've ever bought a home, you know the mortgage process can be a nightmare. What you might not know is that it's actually getting worse, not better.Jim shared a startling revelation: despite decades of technological advancements, the mortgage industry has become less efficient. "The cost today is at a record high for producing a mortgage," he explained. The time it takes to close a loan has actually increased by 10-12 days compared to just a decade ago.The numbers are eye-opening. It costs about $12,000 to manufacture a mortgage loan today. Manual tasks account for approximately $2,200 of that cost. These costs get passed directly to consumers through higher interest rates. Consumers pay for these inefficiencies over the entire 30-year term.Why is this happening? Jim points to fragmented systems and siloed data. "You get stuck staring and comparing data and documents against system data all day long," Jim explains. "As more technology was introduced, you've created more complexity."Jim's solution is simple: Alpha7x has created an "army of digital AI-based agents" designed to replace human labor across the mortgage supply chain. These aren't just chatbots. Alpha7x has built sophisticated agents that handle complex tasks like processing mortgage loans, reviewing closing documents, and performing compliance checks.Jim shared a compelling example: "We did a proof of concept for a large bank doing OFAC checks. I was shocked at the number of people they have doing the process today—15 people manually doing this process. With our agent, they'll need three people."Perhaps most interesting is Alpha7x's business model. They use outcome-based pricing, not seats or licenses. They only make money when they save clients money. "Our incentives are aligned right out of the gate," Jim says. This approach stands in stark contrast to both SaaS vendors who charge licensing fees regardless of outcomes, and Business Process Outsourcers who simply move labor offshore.Alpha7x has also built a tool that allows customers to create new agents without writing code. "We intend to put the power of these agents in the hands of our users," Jim explains. Organizations can rapidly deploy new automation. "They can configure that and have an agent working for them in two weeks."Jim is applying the same principles to his own company that he preaches to clients. "How are we going to ramp this company to 10 million ARR and have less than 20 people? Because that's my goal," he says. "I'm not going to build a people company when I'm trying to talk to people about building agents."This puts Alpha7x in the emerging camp of "$1 million per employee" AI companies. "Drink your own Kool-Aid," Jim advises. "If we're building agents, we might as well act like agents and build a company that is run by agents."While Alpha7x is focused on mortgages today, Jim sees potential far beyond this market. "We could do this in insurance. We could do it in other industries that are data and document centric," Jim says. What sets Alpha7x apart is their deep domain expertise. "What we're building is a micro LLM, a private LLM that understands mortgage regulations and guidelines. That's a much different animal to build."Alpha7x is in an enviable position when it comes to funding. "We have investors knocking on our door that want to invest, and I'm like, 'Okay, we're fine,'" Jim says. "Everybody's like, 'When are you going to do a Series A?' I'm like, 'What would I do a Series A for?'"He continues: "This will print money. It's a high-margin business. We should be able to reinvest that cash in development of the product. From a sales perspective, we haven't even hit go on the sales side, and we're getting calls every day."Jim's advice for entrepreneurs looking to build in the AI agent space is to find domain-specific problems. "Find a niche in a market, own that niche, and expand it," he suggests. But technical expertise alone isn't enough. "You need somebody with domain expertise on your team."With a $15 trillion mortgage market ripe for disruption, Jim Cutillo and Alpha7x are proving that AI agents can transform even the most document-heavy industries.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Elias Torres, founder of Agency and formerly Drift (which sold for $1.2B), joins us to explain why he considers that exit his "biggest failure" and how he's reimagining business building in the age of AI with his new company, Agency.The Billion-Dollar Failure That Wasn'tDespite selling Drift for $1.2 billion, Elias surprisingly calls it his "biggest failure." Why? Because his ambition was to build a $30 billion company that would go public:"My mind for Drift was we were gonna build a $30 billion company. We were gonna take it IPO... And that did not happen, right?"This stark honesty sets the tone for our conversation about what truly matters in company building.The "100 People to $1B" ConstraintElias's new mission is radical: build a billion-dollar company with only 100 employees. It's not just a catchy slogan—it's a deliberate constraint:"I'm trying to create a constraint, right? Because a constraint forces creativity. You have to learn how to manage cost."In his view, when companies grow to hundreds or thousands of employees, the mission changes from serving customers to managing humans:"When you have too many people, it becomes a whole different job... Your focus is how do you feed all those mouths? How do you guide them? How do you coach them? How do you manage their emotions?... It becomes no longer the mission of the company."Why "Seat Pricing Is Dead"Perhaps the most provocative stance Elias takes is on pricing. He doesn't mince words:"I think that seat pricing is dead. I think people ask me all the time and they say, how are you planning to charge it? You know, is it per seat? I think it's a stupidity to charge per seat nowadays."Instead, he's eyeing a percentage of customer revenue—the ultimate alignment:"Why couldn't I have a percentage of your revenue? And that's what I want. Right? It's like, if you don't make money, I don't make money."First Hire: A Lawyer, Not a RecruiterOne fascinating contrast: Elias's first hire at Drift was a recruiter. At Agency? A lawyer. This subtle shift reveals everything about his new approach to scaling:"Most companies delay hiring someone like that. And the founders spent all this time doing all the legal, all the contracting, all the payment, all the financing, all the budgeting."By immediately delegating administrative functions, he's guarding his most precious resource—time.The Extrovert Becoming an IntrovertIn a moment of candid self-reflection, Elias (a self-described extrovert) admits:"I'm becoming more of an introvert with age, right? And I realized that I don't want to interact with people, especially if it is to troubleshoot something for 20 days in a row. It's like, why can't it just work?"This personal evolution mirrors his professional thesis: humans are the "hardest roadblock" to AI adoption, yet they'll increasingly prefer automated solutions that just work.The Secret Lever Most Founders MissThe conversation took a turn when Elias revealed the most underrated growth lever:"Pricing is the most important lever in terms of effort... you make one subtle change to your CPQ or to how you or the number that you charge as the platform price... And that could make or break your business, right? You can increase revenue 50%, you can double revenue."For founders chasing product excellence or distribution, this reminder about pricing's leverage feels like uncovering a secret weapon.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Jaspar Carmichael-Jack, CEO of Artisan, shares his bold vision of prioritizing a single AI outbound agent, Ava, to drive unprecedented customer results. He argues that depth beats breadth in a crowded market, even amid a backlash from their provocative 'Stop Hiring Humans' campaign, which ironically attracted death threats yet skyrocketed their visibility. The conversation also explores innovative pricing models and the crucial balance between AI efficiency and human touch in sales strategies, making for a thought-provoking discussion on navigating chaos in the tech landscape.