Margot Schmorak

I’ve been talking with founders about how painful enterprise customization still is — even in 2025. David Dworsky and Gordon Ritter just put words to what we’ve been seeing: the age of point-and-click configuration is ending, and the next category winners will make customization conversational. For early-stage founders, this is the wedge: - Own one painful workflow - Capture the data - Build toward becoming a system of record If you’re building in this space, I’d love to hear how you’re approaching it. Link to the full article on this in the comments. 

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Leading product teams in regulated environments requires a different kind of discipline. In this episode of the HTD Agile Leaders Podcast, I sat down with Melissa Douros, CPO at Green Dot Corporation, to talk about how product leaders can move faster without sacrificing trust, governance, or customer safety. I enjoyed this conversation on product delivery, AI done responsibly, and what it really takes to lead transformation at scale.

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Just read a piece from the team at Camber Creek portfolio company Proof on the evolving state of authentication…and it hit home. For years I’ve been thinking “passwords are dead,” but also lamenting the difficulty navigating the labyrinthine world of advanced security. This blog lays out exactly what’s replacing passwords in a way that’s practical, not just theoretical. Five methods stood out: - App-based authenticators finally killing SMS (good riddance, SIM-swap nightmares) - Continuous authentication that watches behavior during the session (the “someone stole the cookie but can’t act like you” protection we’ve all been missing) - Adaptive authentication that doesn’t treat grandma on her usual iPad the same as a login from a Tor exit node in a new country - MFA done right (and then taken further with verified digital certificates) - Biometrics with actual liveness + document tying, so it’s not just “a face” but your verified face What really resonated was the reminder that the strongest systems aren’t about piling on more factors; they’re about using the right factor at the right moment. Risk-based, context-aware, and (crucially) user-respecting. I’m biased but Proof’s angle of anchoring everything to high-assurance digital certificates feels like the missing glue. It’s one thing to authenticate someone at login; it’s another to carry that verified identity forward through the entire session, signature, or transaction. This one is worth the read. Link in comments. #venturecapital #cybersecurity #fraud

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Seth Levine nailed it! The concentration problem isn't just a GP pain point... it's choking innovation. When capital pools around the same 20 funds, emerging managers and founders get shut out. Love that he's using his platform to call this out. Foundry has backed 50+ emerging managers. That's the diversification the ecosystem needs. This is exactly why Carta exists — making capital allocation visible and accessible. Capital Evolution hits at exactly the right moment. Thanks for having us Daniel Dart. Team Carta loves the community of FUTURE TITANS you have built 🚀

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Too many SaaS companies are trying to manufacture a category right now. At seed stage, it feels audacious (and fundable). At Series B+, it still sounds good on a stage... But if your endgame is mid-market and enterprise, the reality can be harsh: ❌ Enterprise buyers don’t typically budget for nascent categories - and are typically quite slow to spend on and test newly established categories. 🫰They budget for problems they already know how to fund...the ones that have the leadership/procurement paths pre-carved out. That’s why category creation is almost always boom or bust. You’re not just selling software; you’re teaching buyers to name a problem, shift priorities, and convince slow moving enterprise bureaucracies to approve net-new budgets. Most companies don’t have the time or capital to push that uphill for prolonged periods of time. Slotting into a known category may sound less visionary, but in enterprise it often wins faster... ✅ Budgets already exist. ✅ Stakeholders already understand the space. 🤝 Your job is to show why you’re the obvious choice - clearer, faster, better, yada, yada... you get it Known budgets + defined buyers? Slot in, then differentiate ruthlessly. Unnamed problem + no budget line? You’re playing a long game. Make sure you have the war chest to survive it and the end outcome is worth it (tbf, typically with VC companies these go hand in hand). Snowflake and Gong pulled off category creation because they had capital, time, and undeniable customer impact. Snowflake's CMO, Denise Persson has talked about the extreme messaging consistency and endurance that was required to come out the other side. Most don’t have the time.⏳ Datadog, Zoom, and Okta won big without inventing a category. They just dominated one that mattered to enterprises. Category creation has become a crutch for founders and marketers. In enterprise, it should be the exception, not the default.

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The GTM playbook is being rewritten — and CROs are leading the charge. Last week, Scalestack co-hosted an unforgettable CRO Roundtable in San Francisco with our friends at The CRO Collective. 👥 20 revenue leaders 🌆  An iconic venue at the Transamerica Pyramid 🔥 Real, unfiltered conversation No panels. No pitches. No filler. Just honest conversation around what’s working, what’s not, and where we go next as GTM continues to shift beneath our feet. Some themes that stood out: 🚨  Misaligned incentives are killing revenue strategy 🎯  Marketing ≠ just lead gen — it’s about brand, education, and long-term growth 🧠  Millennial buyers demand a new approach 🤖  AI is non-negotiable — but hard to navigate 🏗️  CROs aren’t just sales leaders — they’re system architects Scalestack is building revenue engines that work with the GTM stack, not around it. That’s why these spaces matter: they cut through the noise and make room for clarity, curiosity, and collaboration. Big thanks to the leaders who showed up ready to challenge assumptions and push the conversation forward — and to our partner Warren Zenna, and the team at The CRO Collective for making it all happen. Looking forward to the next one! #Scalestack #CROCollective #AutonomousRevenueEngine #RevenueEngineMasters #CRORoundtable

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