Relay by Chargebee

As we stand in 2025, we stand amidst a lab of sheer magic. Each day brings a maddening reshaping of perspective. It’s evident that AI is fundamentally challenging the mechanics and economics of SaaS as we know it. So, in an attempt to render this moment in some practitioner’s grounding, we are thrilled to share a new Relay by Chargebee ???????????? ?????????????????? ????-???????????? ???????????????? ?????? ?????????? ???????????????? ?????????????? ??????. ??? These stories, collectively, will be a documentation of and an inquiry into the new playbook of building and selling software, and of the central role that the monetization lever will play in this evolution. Last week we published an excellent, first contribution from Question Base’s (a human-verified, ai-driven, always-learning knowledge base on top of Slack) co-founder, Yana Tornoe. She shares how they’ve built their data layer for differentiation from ground up, the way they look at Slack’s own AI offering, managing high-stakes hallucinations, per-seat pricing, and so much more. → I especially found her note on their ???????????????? ???????????????? very interesting. While striking a balance between growth and sustainability has always been key to getting freemium right, the unique specifics she shares on what that has looked like in an AI-native setting were instructive. Join me in kick-starting the series by giving this post a read and if you have any questions for Yana, feel free to ask her on Relay or drop them below. Looking forward to bringing you a lot more of these in the coming weeks! Much to learn. PS: link to article in comment for easier access.

As we stand in 2025, we stand amidst a lab of sheer magic. Each day brings a maddening reshaping of perspective. It’s evident that AI is fundamentally challenging the mechanics and economics of SaaS as we know it. So, in an attempt to render this moment in some practitioner’s grounding, we are thrilled to share a new Relay by Chargebee ???????????? ?????????????????? ????-???????????? ???????????????? ?????? ?????????? ???????????????? ?????????????? ??????. ??? These stories, collectively, will be a documentation of and an inquiry into the new playbook of building and selling software, and of the central role that the monetization lever will play in this evolution. Last week we published an excellent, first contribution from Question Base’s (a human-verified, ai-driven, always-learning knowledge base on top of Slack) co-founder, Yana Tornoe. She shares how they’ve built their data layer for differentiation from ground up, the way they look at Slack’s own AI offering, managing high-stakes hallucinations, per-seat pricing, and so much more. → I especially found her note on their ???????????????? ???????????????? very interesting. While striking a balance between growth and sustainability has always been key to getting freemium right, the unique specifics she shares on what that has looked like in an AI-native setting were instructive. Join me in kick-starting the series by giving this post a read and if you have any questions for Yana, feel free to ask her on Relay or drop them below. Looking forward to bringing you a lot more of these in the coming weeks! Much to learn. PS: link to article in comment for easier access.

??When foundational models race each other to the “bottom” (highest performance at lowest cost)… ??When the same data is used, misused and overused… ??The main game in AI now is capturing user interactions ?? …. Craftsmanship in tool-making matters more than ever. But only if you’re solving real customer problems.?? …. If you could survive before with mediocre product that somewhat solves a problem, you’re game-over in today’s market. The race for the best is ???N. And it’s about top performance at every step of the customer journey. … It’s never been easier to get in business. It’s never been harder to stay in! … I feel we’re strong contenders for this era. Let’s gooo, guys! Kasper Tornoe Stefan Vladimirov

"The winners [in AI solutions] will be the ones who manage to gain a UX advantage and..." ???? ?? Thrilled to share the newest of Relay featuring Question Base's co-founder, Yana Tornoe! In this chat, Yana shares her learnings from building Question Base including AI’s “Very Real” cold start problem, managing high-stakes hallucinations, and balancing adoption and costs with a freemium strategy. She also shares (in her words): → use cases → the power of knowledge + AI → immediate gains → roadblocks for implementation, and more. Read the full story in the comments below! ↓ And if you are a founder, get your Relay invite, if not already.?(Comment for it!)

Founders: Did you choose the clarity and speed of building in mature markets, or the challenge of creating within emerging markets? ?? For Andrew Lau, co-founder and CEO of Jellyfish, the choice of building something new was a deliberate one. On this episode of Second Acts, he joins Chargebee’s CEO, Krish Subramanian, to share hard-won lessons from his two-decade journey: from leading engineering at Endeca (a startup that eventually saw a $1.1B exit to Oracle) to being a serial founder, and now, pioneering a new category in engineering management with Jellyfish. Andrew and Krish also explore: — The foundations that helped Jellyfish accelerate during (and beyond) the pandemic — Why they chose a mid-market strategy over the typical SMB or enterprise-first approach — How scaling up is as much about managing capital as it is about patience — And much more! ?? Tune in to hear Andrew’s no-fluff perspective on category creation — and why it’s worth the extra noise and slower sales cycles. Find the ?? below. #SecondActsPodcast #SaaS #Scaleups

Founder-market fit is rarely used accurately. It is often brought up to describe a founder/team that has past experience with or special affinity for a particular problem statement. But that’s just a part of it. The other (in my opinion, more consequential) part concerns go-to-market alignment. That is, does the way you choose to market/sell/monetize reflect your strengths, preferences, and long-run goals? Mostly, no amount of customer/product obsession can overcome this misalignment especially when it comes down to scaling. In the latest Second Acts episode, Jellyfish co-founder and CEO, Andrew Lau, brilliantly lays out how they deliberately sought that GTM-fit with a mid-market motion and had to prove (and fight!) that that would scale better than both PLG and enterprise plays. Andrew also shares: — why they took the category-creation path while acknowledging its trade-offs, — why they’re building Jellyfish for engineering leaders, — what ‘it tasted like to learn to close deals’ as a technical founder, — how he first met his co-founders all the way back in 1999, — how to think (honestly) about the inherent unpredictability of everything, — and so much more! It was a great pleasure talking to Andrew. Don’t miss the episode (links to watch/listen are in the comments below).

The first obligatory thing to mention when talking about Crossbeam co-founder, Bob Moore has to be the infectious relatability with which he speaks of the very real struggles of starting and scaling up. The next thing to note are his delightful, remarkably precise analogies (there’s one in the clip below) on everything. He is also a serial founder, started up first time during the peak of the great recession, and he foresaw two massive SaaS categories incredibly early. So it was a pleasure to speak with him for the latest episode of the Second Acts podcast. In our conversation, Bob shares: — how RJMetrics lost product-market fit *because* they had chosen to double down on what was working, — the story of an intense, 6-month period when the timelines of RJMetrics (acquired by Magento), Stitch (acquired by Talend), and Crossbeam, coincided, — the bundling-unbundling cycles and how they’d play out with AI, — how humanly he has approached competition, — how ecosystem-led growth unlocks the next S-curves, — why M&A deals are often set up to fail, — the humbling experience of doing 200+ (fascinating, right?) improv shows, — and so much more! Don’t miss this episode. Links to watch/listen in the comments below.

What really happens when a founder says, "you know what, you take it from here"? In the latest episode of Second Acts, we explore one of the toughest decisions a founder can face with DataSnipper's Co-Founder Jonas Ruyter and CEO Vidya Peters. Together, they walk us through: ?? Why Jonas and his co-founders made the bold move to hire an external CEO? ?? How Vidya approached this opportunity with a beyond-the-headlines mindset? ?? How Jonas found new ways to contribute as a founder For SaaS founders and execs, this episode carries earnest insights on leadership transitions, scaling effectively (they raised a massive $100m series B earlier this year), and staying agile in a high-growth environment (they serve 500K+ active users across 125 countries). ?? Listen/watch now: Spotify: https://lnkd.in/ggWf9QYq Apple Podcasts: https://lnkd.in/gSrMSJBR YouTube: https://lnkd.in/gbnBw9tm #SecondActsPodcast #SaaS #Scaleups

“Fix the roof, when the sun is shining.” The moment I heard DataSnipper’s CEO,?Vidya Peters, share that operating value, I was immediately reflecting on those moments when I could have done exactly that. Because growth, as is its blinding nature, papers over everything. It doesn’t just blanket the smaller, troubling symptoms. Even structural, org-wide issues can go unaddressed (or rather, completely ignored). And, at scale, most things become much worse if you catch them late. As Vidya, beautifully advocates, an essential scepticism coupled with an urgency for driving continuous improvement across the board, is a vital practice. Because no matter how good those growth rates seem today, I can attest, there’s always (always!) room for massive improvements. Why not pursue them when times are good?It was a great pleasure hosting Vidya and DataSnipper’s co-founder,?Jonas Ruyter, for the latest Second Acts episode. The chat was centred around how Jonas and his co-founders decided on hiring an external leader as a CEO (a quest that led them to Vidya), and how thoughtfully they’ve brought that transition about. But given their astonishing clarity on scaling and the openness with which they spoke about some of its difficult parts, we ended up covering so many foundational ideas that contribute to enduring, outsized success in SaaS. Do give this a listen (links in the comments below)!?

“Most people aren’t looking for best-in-class products. They’re not looking to innovate with their stacks. They just want to get their jobs done with the minimum amount of hassle and context switching.” ?? ?? ?? ?? In Relay’s latest, Goldcast’s co-founder, Palash Soni, makes the case that, increasingly, B2B users prefer the clear, extensive practicalities of all-in-one/compound products over the saturated, often disconnected experience of using even the best point solutions. He also dives into ???? → Why the state of a market matters more than its size → An abiding lesson from his time at InMobi → Enduring post-pandemic headwinds → Building for an always-in-flux function → Why their CS and sales orgs operate incredibly closely → And more! Check out Palash’s complete interview here: https://lnkd.in/gd3_Fkaw