Shiren Vijiasingam

OpenAI is one of the defining companies of our time. I can't actually believe we at Clay get to play an (extremely) small part in helping them grow. Here is that story. We met Keith Jones 🚴🏻‍♂️ — who leads OpenAI's GTM systems team — through Maggie Hott in December of 2023. To put it mildly, Keith was skeptical. He even gave us a test in our first demo. He had just joined OpenAI 3 weeks prior, so he was sure we wouldn't be able to accurately find him in Clay, but we successfully did during the demo — in just a few seconds. Now, more than a year later, Keith says: "In my professional opinion they have one of the most practical and exciting applications of AI, in a decades-old practice that has long been stale" What drove this conclusion? ▶️ More than doubling inbound lead enrichment quality from low 40% to high 80% during implementation ▶️ OpenAI used Clay’s AI web researcher to mimic and augment the research process of their best sales reps—at scale—leading to countless hours saved. ▶️ Instead of using a dozen tools, OpenAI's sellers can now get any enrichment they need—from contact info to account research—with one click in Salesforce. But we aren't stopping there. We're working with data science, marketing ops, and recruiting to help them harness the power of Clay for their workflows. And as their team (hi Scotty & Harsha!) continues to come up with new ideas to grow, we'll be there helping them bring those to life. Full case study link is in the comments!

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Red flags I’ve learned to spot in customer relationships - from 12 years in the trenches: After years 12 in Customer Success, Product, and HealthTech I’ve learned that churn rarely happens overnight - it starts as a whisper. Here are the signs I listen for👇 🚩 "We’re too busy for onboarding right now.” At Blue Cross, I learned: customers who skip structured onboarding churn 3x faster. Now, onboarding isn’t optional - it’s mission-critical. 🚩 Low usage but "everything’s great.” Data doesn’t lie. At HCA, tracking telehealth logins helped me spot adoption issues early. Fixed one provider’s workflow and doubled virtual visits in 60 days. 🚩 The executive sponsor disappears after kickoff. If leadership isn’t engaged, the account is already at risk. I escalate this at Day 30, not at renewal time. 🚩 Recurring support tickets on the same issue. At Hypeline, I documented patterns and turned them into process improvements. Cut repetitive requests by 20% in two months. Band-aids don’t work - fix the wound. 🚩 Customer only reaches out when something’s broken. Reactive relationships don’t renew. I schedule proactive check-ins even when things are "fine.” 🚩 "Can you just add this feature?” without context. Feature requests are symptoms, not solutions. My go-to question: “What outcome are you trying to drive?” The fix is rarely just a feature. 🚩 Silence after delivery. The quietest customers churn the loudest. At Hypeline, gathering post-delivery feedback (4.7/5 avg. satisfaction) helped surface hidden risks early. The best CSMs treat early warning signs like smoke detectors - not fire alarms. By the time you’re fighting churn, it’s already too late. 12 years in, I’ve learned Customer Success is part detective, part therapist, part data analyst. What red flags have you learned to catch early? #CustomerSuccess #ChurnPrevention #CSM #HealthTech #SaaS #AccountManagement

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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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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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GTM Engineer might be the hottest title in tech right now, but the work has always been there. Some wear the title. Others just do the work, connecting systems, stitching insights, enabling teams, and pushing go-to-market efforts forward without the fanfare. Whether your org calls them GTM Engineers, Revenue Ops, or just “the person who makes everything work,” they’re often the difference between activity and real impact. If that’s you, this asset will help. It’s a clear, no-fluff breakdown of what great GTM execution looks like and how to improve it. Built to support the people behind the motion. Enter Peel Playbook - GTM Engineer Edition (of course as a Talkable) Talk to it - steal the great ideas - link in comments

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I was recently asked whether AI will kill SaaS. My opinion is more nuanced than a simple "yes" or "no." I think the death of SaaS will happen slowly and then very suddenly and very dramatically. I'm talking particularly about mid-size SaaS companies (say between $100 million and $1B). If you're not AI-native right now, you're going to struggle. 9 out 10 of middle-market companies are seeing some churn, but the churn isn't dramatic yet. There's employee attrition. These companies are fighting a war, feature by feature, adding a little "AI pixie dust" here and there. But net: they're struggling. There will be a tipping point in the future where credibility tips to the new fast-growing startups and away from the incumbents. We can already see that people are buying for outcomes instead of buying for seats. The billion-dollar companies will have enough cash to spend their way out of this problem, and these mid-sized incumbents will get squeezed. The question isn’t if the tipping point comes. It’s who shows up with a product that actually does the job and evolves faster than the models. Right now, we should all be paying attention to the tiny AI-native startups that are growing like crazy - especially if you’re sitting in that middle-market range.

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most positioning dies in a Notion doc founders say they want crisp messaging, but what they really need is **confidence** 💪 confidence that GTM teams will *actually* use it 💪 confidence that it’s differentiated 💪 confidence that it scales confidence is what I aim for when I work with early-stage teams it’s not about who has the best positioning framework it’s about end-to-end frictionless adoption throughout your org p.s. what are your PMM tales of woe? (where your hard work sits on a digital shelf collecting dust)

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