Relay by Chargebee

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

Jason Cohen, founder of WP Engine, has seen it all—two bootstrapped exits, two unicorns, and countless lessons on the art of scaling smart. 🧠 👉 From how to manage the chaos of scaling with predictability to their uniquely placed bet on the enterprise segment (and other second acts of scale), Jason shares the lessons that shaped their journey to 200K customers and $300 million in funding. Watch/listen to this episode of Second Acts wherever you get your podcasts 👇 Spotify: https://lnkd.in/gQgv9SyH Youtube: https://lnkd.in/gHFgn2ch Apple Podcasts: https://lnkd.in/gTci6had #SecondActsPodcast #SaaS #Scaleups

A common consideration for approaching second acts (whether that’s entering new segments/markets or introducing new product lines) concerns the size of the opportunity. Essentially, how big and enduring will that next S-curve be? In our conversation for the Second Acts podcast, WP Engine’s founder, Jason Cohen, beautifully notes a different, obvious-seeming consideration that’s often overlooked: one’s own strengths. Is your monetization model set up in a way that gets you a ready advantage with a new segment? Does your product allow for an immediate expansion into a new vertical, even if you need to rethink go-to-market? Jason illustrates how their move towards enterprise customers, despite them having to structure entirely different marketing and sales teams, still came from a position of strength because they sold the same product. “You’re not leveraging the assets you’ve built. You’re not leveraging the capabilities you have. It’s like going off into another business. That’s not smart. What’s smart is we got to leverage what we already have built, what we already can do, and then just pivot this area, pivot that area, to go into [something] new.” This conversation is packed with similar, hard-won know-how that Jason has gathered over 24 years of scaling software businesses. For example, towards the end, I asked Jason, what was to be the final question, and he delivered a a 20-min masterclass on strategy. :) So, definitely check this one out (links in the comments below).

Great chatting with Relay about our approach to building Flat. TL;DR: we invest a ton in understanding how Flat fits into a team's culture and environment and why they do things the way they do. It's a really fun, really hard problem.

“You’ll often hear that the collaboration challenge can’t be solved by technology, because it isn’t a technical problem, it’s a cultural problem… There’s truth in there. But we think it’s a bit more nuanced than that. Because technology has the ability to make things hard or easy.” 🚴♀️✨✨ 🗞 In Relay’s latest, Flat’s co-founder, Seth Purcell, talks about how by ascribing too much weight to cultural influence on user behavior, B2B builders end up downplaying technology’s as-crucial role and miss out on shaping truly user-centric products. He also dives into 👇👇 → How they define niches at Flat → Why some free tier users pay them voluntarily → Why they’ve chosen the harder path for driving adoption → Why they don’t just want to build a “simple” product → And more! Check out Seth’s complete interview, here: https://lnkd.in/g-i-b9nr

I’ve been thinking a lot about something profound that Wistia’s co-founder, Chris Savage, shared in this new Second Acts episode. He mentioned how, as a company that’s been around for a while, it’s tempting to consider that your work is at the centre of your chosen category. It’s tempting to suppose that just because you’ve matured as a business, the market has matured in lockstep. It’s tempting to assume that competition is won and done. As Chris says, in SaaS especially, you cannot be more wrong. The ICP. The competitors. The core problem statement. And everything else is changing all the time. Even in our space, we’ve seen some new entrants that are taking a completely different approach to the category. What does it mean for a scaling business? Primarily: That scale shouldn’t blind you to the changing realities of the market and of what customers are beginning to imagine in terms of what they want from potential solutions. There are many other such deeply felt insights from the Wistia journey, in this conversation that I had with Chris and his co-founder, Brendan Schwartz; it was such a great pleasure to host them! Starting with how Wistia’s act two unfolded the one time they decided to sell the company, why they believe (and I completely agree) if someone isn’t a world-class IC they cannot be a world-class exec/manager, how they ship exceedingly fast at scale, and more! Catch the full episode (links in the comments below)!