Podcast
SAAS Operators
Hosted by SAAS Operators · EN
3 CEOs from some of the fastest growing software brands and Jack trying to get as much information out of them as possible.
18episodes
Episodes
Newest firstAll episodes
E55: AI Native Teams with Jacob Posel from HQ
3d ago00:45:00Tap to summarizeIn this episode of the SaaS Operators Podcast, Jacob Posel joins Jeremiah, Jack, and Rishabh to talk about HQ, a cloud-based file system built on top of Claude Code and Codex that launched two days before recording.The origin story is good. Jacob meets Corey Epstein, sees a product called Indigo that was ahead of its time but waiting on AI to catch up. They stay in touch. Corey eventually puts Jacob on an internal tool called HQ. Jacob gets hooked, starts pushing the team to build a version for multiple people, and when Ramp published their internal Glass tool, Jacob tweets that they built Ramp Glass for everyone. The demand comes in fast, so he joined the company.The core problem HQ solves is one that Jacob kept running into across every business he consulted with. AI tools are built for solo use. Everyone's working in silos, repeating work, building their own janky version of the same thing. HQ gives teams a shared cloud workspace where skills compound. One person's breakthrough becomes everyone's baseline.Then the conversation goes somewhere more interesting. Rishabh pushes on who actually buys this. His argument is that the buyer isn't the average CEO, it's the founder, because founders are transformers and CEOs are optimizers. The person most likely to get value from HQ is someone who's willing to stay on the treadmill as the technology keeps moving, not someone who wants a finished system handed to them.Jacob's take on pricing is worth sitting with. A customer costs about a dollar a month to serve. The play is distribution. Get HQ into as many businesses as possible, stay close to how people interact with AI, and the monetization builds from there.The episode closes on something most people aren't saying clearly. Getting your team AI native isn't a software problem or a gamification problem. It's a coaching problem. And right now the gap between the people doing it well and everyone else is enormous.
Transcribe →E54: Become AI Native with Jim Benton from Adapt
2w ago00:49:11Tap to summarizeIn this episode of the SaaS Operators Podcast, Jim Benton, CEO of Adapt, joins Rishabh, Jeremiah, and Jack to talk about what it actually looks like to build a company brain.Adapt connects all your tools, GitHub, Linear, HubSpot, Notion, Slack, and instead of scheduling tool calls one at a time like an MCP would, it swarms them. Hits everything at once, pulls the data back, and runs the best available model against it. That's why people say the answers look and feel different to Claude.The land vs. expand question kicks things off. Jim's take is that landing still matters, you've got to cut through the noise, but the real unlock is frictionless self-serve. Get people connected to a few tools fast. Let them hit the aha moment on their own. He tells a story about a CEO who signed up on a weekend, connected several tools, ran queries, and put a card in before sales could even reach out. That's the model.Jeremiah's been using Adapt long enough to notice his spend is about four times what he budgeted when he signed up, but he's not complaining. He understands what the brain means for token efficiency over time, and how sitting closer to the data gives you a real structural advantage over just piping Claude directly into your stack.The conversation gets into AI adoption inside companies, and it's not who you'd expect resisting. Senior executives are rolling their sleeves up. Younger employees in delivery roles feel the threat more directly. Rishabh's EA told him her goal is to have Claude handle 100% of her tasks. Jim's response is nuanced: the EQ parts of the job still need to be human. What you want is AI handling the computer thinking, and people doing the people thinking.Jim closes with what Adapt is actually becoming. A proactive reasoning engine. Something that spots the pattern you never thought to ask about, cross-references a product decision from six months ago with a deal you lost last week, and brings it to you before you knew you needed it.TLDR: The AI natives don't want to work with the non-AI natives. Get in or get left behind.
Transcribe →E53: GaaS for SaaS with Ronak Shah and Ankit Patel
4w ago00:44:46Tap to summarizeIn this episode of the SaaS Operators Podcast, Ronak Shah breaks down what the best SaaS brands look like from inside Gaas for SaaS.Rokt gets the top spot. Smaller than the others, but the most intentional operators on the list. They get the pay it forward model, they activate partnerships, and they understand that feedback is its own thing, separate from conversion. Proxima rounds it out, having graduated from e-commerce SMB into an enterprise play with Microsoft.The through line? The best SaaS operators are calm about AI. Engineers who've sat through a few hype cycles know that 90% of what's making noise right now isn't going to land.Then Jack pulls up a landing page he vibe coded with Profit AI. A Shopify page built by an agent using a VideoWise reference. Shoppable video widgets. A coupon code that redirects to checkout. The agent scraped the videos, built the section, and added features Jack didn't ask for.Jeremiah's take is that AI is putting a ceiling on what people will pay for SaaS. The build-it-yourself option has a real price now, and brands are going to start doing the math.Ankit brings the most grounded take of the episode. AI has unlocked the generalist. One person doing packaging, ads, landing pages, and branding without a team. He's running the experiment on Avi right now. 100 AI generated static ads aren't moving the needle any more than 15 hand-crafted ones did. Output is one thing. Impact is another.The conversation closes on something most people won't say out loud. Enterprises asking how to get on the right side of AI are going to get outcompeted by 2 people, a blank slate, and a stack of agents.TLDR: The tornado's coming.
Transcribe →E52: How AI Replaces People with Chase Mohseni from Creative OS
Apr 2901:15:13Tap to summarizeIn this episode Jack, Rishabh, Chase and Jeremiah talk about how AI is changing the way they run their teams day to day. Rishabh challenged Chase on why he keeps getting pulled into problems, and his read was that Chase wants to keep his finger in the pot, so the honest move is to admit that and pick two things to drive well.We got tactical on how each of us is actually using AI right now. Rishabh has FERMÀT MCP connected to every internal system, customer data, and their own product, so he can build customer decks while pushing his daughter on the swing.He thinks humans are better deployed as empathy and joy centers, and computers should do the thinking. Chase has trained his AI tools to tell him when he's being dumb and they've literally told him to put the laptop down and go to bed. Jack shares how he built a QA skill that uses agent browser to test every piece of functionality in his app after each change, and recently watched it set up TikTok Shop and Amazon integrations from start to finish without him being involved.Chase walked through where Creative OS is heading. Canva, Figma and Adobe are going to eat the horizontal creative market, so they're going vertical on performance creative and building what he calls the creative loop, spark of an idea to finished data backed asset. The 90 day plan is to make everything work seamlessly inside Claude, Cursor, or whatever IDE the customer wants to work in. Rishabh pointed out that specialist roles are going away regardless. AI gets everyone to the 90th percentile easily, the 99th percentile is still hard and always will be. He's hiring high agency, high grit, high horsepower people and is indifferent to what they're specifically good at. We closed on the reality that we're all in an AI pilled bubble. Chase's wife works at a big company that just told employees they can maybe try ChatGPT if they want. There are hundreds of millions of people who haven't downloaded Claude yet and have no idea what we're talking about.
Transcribe →E50: The Future of Software Businesses with Maxx Blank from Triple Whale
Apr 800:54:45Tap to summarizeThis podcast features an in-depth conversation with Maxx Blank, one of the co-founders of Triple Whale. Maxx shares the company's journey from a simple ecommerce dashboard that Maxx wanted for his own Shopify brand, to an AI-native data platform that serves over 30,000 of the fastest growing Shopify stores. We talk about internal tensions (fighting at work) and leadership approaches when navigating a rapidly shifting technology landscape. As well as some uncomfortable truths. Maxx Blank has built an incredible business by asking the same question every Shopify's store owner asks, how does this make us money? With billions of dollars of orders flowing through Triple Whale, they have a pretty good idea.
Transcribe →E49: How To Build An App That’s Worth Buying with Varun Kundra
Mar 3000:53:03Tap to summarizeIn this episode of the SaaS Operators Podcast, Varun Kundra , co-founder of AfterSell, talks about how the business was built around post-purchase upsells on Shopify. The core product sits in the window between checkout and the order confirmation page, a moment where conversion rates on relevant offers can hit 5-15% when set up properly, and where the highest-performing stores see the biggest AOV lift. Varun walks through how AfterSell eventually caught the attention of ROKT, a much larger company running third-party offers in the same post-purchase space, which ultimately led to an acquisition.We talk about the decision to sell at 23 years old, and what drove it. AfterSell had incredible traction, but there’s a belief that the Shopify ecosystem has a ceiling. The list of companies that have scaled to meaningful size inside it is short, Klaviyo, Recharge, a handful of others. The exit to ROKT gave Varun and his co-founders liquidity and something arguably more valuable, a front-row seat to how a larger, well-run business actually operates. Management, performance reviews, culture building, commercial strategy. None of that existed inside AfterSell before the deal.The back half of the episode opens up into a broader conversation about management philosophy in a fast-moving environment. Rishabh makes the case that a lot of traditional management principles, like giving criticism in private, were built for a world where information moved slowly. That world is gone. Jack and Rishabh talk through what it looks like to run a team where almost everything happens in public channels, why top performers tend to self-select in that environment, and where the ethical lines still hold. Varun ties it back to the meta-skill that survives any wave of technology: learning how to run a business where the value you deliver exceeds what you charge, and what you charge exceeds what it costs to deliver.
Transcribe →E48: From Service to SaaS with Aaron Schwartz & Daniel Brady
Mar 2301:05:18Tap to summarizeIn this episode Aaron Schwartz and Daniel Brady, co-founders of Orita, joined us and we talked about how they built an ML-powered audience intelligence product for e-commerce brands. Orita tells you which customers on your list want to hear from you, when and what about. It started as a consulting project where 5 out of 6 cold-outreached brands booked a meeting in under thirty minutes, it grew entirely through word of mouth, and the founding team was only 2 machine learning engineers.A near-perfect close rate was a pricing signal they couldn’t ignore. DB and Zach were only charging $50 a month to manage a brand's entire email strategy. Aaron doubled the price on the next three pitches and closed all three. We talk about how every retention tool hits a ceiling eventually. How retention as a category has a budget, which determines what a founder or CFO approves, regardless of the ROI in the dashboard. For some brands, Orita generated a 17x return and still got cut because the line item looked too big for a retention budget. That's what pushed the team into performance marketing, ads and direct mail, where buyers think in multiples of spend and the ceiling moves with results.Rishabh makes the case that Shopify warps the ecommerce founder's expectation of the cost of SaaS, because the real cost is buried in payment processing fees, and that gap shapes what merchants are happy to pay for every tool around it. DB talks about how he makes the every day decision on what to build and what to ignore, which features get commoditized in 3 to 6 months, and which ones require years of domain data, expertise and ML depth to replicate. The answer is some mixture of stay on the hard problem, build something durable, and outlast the noisy low value competition.
Transcribe →E47: Building The World’s First AI Creative Strategist with Alex Cooper & Maneesh Apte
Mar 1701:06:42Tap to summarizeIn this episode Alex Cooper and Maneesh Apte, two of the co-founders of Parker, joined us to talk about building an AI creative strategist that lives inside your Slack channel. Parker feels like a senior hire on your team. It sends you ideas without you asking. It tells you when something is a bad fit for your brand. It’s the product Alex Cooper was asking for, built by marketers that ran creative strategy for some of the fastest growing consumer brands, and you can feel it when you use it.We talk about how the Parker launch did 1.4 million views in 24 hours. How X took the post down all because a launch partner congratulated the team publicly and someone at X flagged it as a paid promotion. Alex Cooper had to speak to Nikita at X and Elon Musk’s brother to get his account reinstated. They hired 3 people in 12 hours to handle all the sales calls and blew past 1 million dollars in annual recurring revenue almost overnight. Rishabh brings up a piece from a16z about cornered resources and network effects being the only 2 moats that still matter and we get into where Parker's moat actually is. The integration layer is commoditized. Anyone can connect Reddit, TikTok and YouTube to a dashboard over a weekend with Claude Code. But documenting how top strategists actually think takes years. That's the layer Parker is building on.We talk about why dashboard-only tools and workflow-only tools are both going to struggle. Why most companies are further behind on AI than you'd think, and why marketing agencies are becoming Parker's best customers.
Transcribe →E46: Acquiring Marketing SaaS & Agencies with Chase Chappell
Mar 900:51:13Tap to summarizeIn this episode Chase Chappell, the founder of Sirge, Success AI, Ads Mastery and Partner at DOE Media, joins us to talk about building a vertically integrated e-commerce operation, acquiring marketing agencies and smaller SaaS companies, and why personal brand is still the biggest moat in a saturated market.We talk about Block's 4,000-person layoff and what it says about how the public markets now value software companies. Zach makes the point that AI is great at cutting costs but nobody's figured out how to use it to make dramatically more money, and how solving that problem is not obvious.Chase breaks down his approach to acquiring TikTok shop agencies, email firms, and smaller SaaS products, why he cuts the bloat immediately, and what he's actually looking for when he brings a new team in. He also gets into the problems with AI creative generation tools, reliability. The generations look great until your logo gets redrawn and your font comes out wrong.Chase Chappell is deeply integrated in every part of ecommerce, and it shows.
Transcribe →E45: Swiping Left on Ads Like Tinder with John Gargiulo
Mar 200:54:10Tap to summarizeIn this episode we talked to John Gargiulo, the founder of Airpost. Airpost makes new video ads every week for enterprise advertisers spending $1M or more a month on Facebook ads. They've got human creative strategists using a UGC footage library, AI generated clips, and an engine that orchestrates all of it into 10-40 net new ads per client per week. Some of his clients never open the platform. They get a Slack message saying ads are ready, upload them, and run.It’s an agency with full agency, and a little bit of saas.Everyone tried something new with AI. Rishabh talks about how he built an MCP in an afternoon, started using Claude to interact with his own product, and said it was better than the UI his team built. Zach used Cowork to do 3 years of tax credit documentation that would've cost $65K through Deloitte and it only took him half a day.John was running 10 Cowork windows at once, and compared it to running 8 slow cookers in a kitchen.We talked about per-seat pricing dying once customers demand MCPs. The 10/80/10 model came up too. 10% is direction, 80% is execution, 10% is evaluation. That 80% of leverage might be headed toward 98%. The only part that doesn't get handed to an agent is the judgment call. What to build, where to aim, and whether it's actually good.We talked about how AI is actually making your day harder. When the busywork disappears, every hour is focused on real decisions. You become the bottleneck to your own agents. And the people pumping the brakes? Usually working through something emotional. The question everyone keeps circling is what do humans do when AI can do the work?
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