Jamie Kanter

Kyle James makes a great observation about how GTM teams are approaching platforms like Gainsight today. What looks like hesitation is often discipline. Teams are taking time to pressure test workflows, data, and ownership before committing to a platform. That behavior does not diminish the value of Gainsight. In many cases, it increases it. When teams arrive with clearer intent and operational readiness, adoption improves and outcomes compound faster. The signal here is not about building instead of buying. It is about earning the right to scale with the platform once the foundation is actually in place. https://lnkd.in/emF9ZvCQ

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"How can CS be a revenue-driver when I can fire half my team and NRR stays the same?" Until Customer Success can find quantifiable evidence that they have a higher ROI than another AE hire, they'll always be a cost center. That's what happens when you solve for churn. You start playing not to lose. You meet with every account regardless of tier. You fret over each escalation, not by the amount of ARR at stake, but by how angry the account seems. Fear of conflict drives your decision-making. You have every customer insight at your fingertips. You have 360-degree customer intelligence. You reach out proactively at the first sign of trouble. But it doesn't make a difference. And it won't. Because the people who make CS tools are ALSO solving for churn. And CS can't be accretive with tools made for support and risk reduction. Just listen to the man himself: "Customer Success has gotten worse over the years. Much worse…We're seeing a fundamental shift where CSMs are expected to be revenue generators, but they're using systems designed for customer support." - Jason M. Lemkin If I'm honest, I'm kinda over Customer Intelligence. And I'm not even 100% sure what Commercial Intelligence is. We need Expansion Intelligence. #customerexpansion #nrr #customersuccess

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Most SaaS sales organizations don’t struggle with execution rigor. They struggle with what happens after rigor is introduced. Deal standards improve. Qualification language tightens. Forecast calls sound sharper. But under pressure, something breaks. Coaching collapses back into deal inspection. Managers review what is happening, not why it keeps happening. Skill gaps stay invisible until results flatten. The system holds. The capability doesn’t. Execution rigor without enforced coaching standards eventually eats itself. Most CROs don’t see this as a leadership problem at first. It looks like noise. Or variance. Or a talent issue. By the time it’s obvious, the damage is already done.

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The territory allocation debate in SaaS sales is the worst debate of 2025. And the only reason it keeps resurfacing is because people still treat SaaS like a field-sales operation. There are industries where territory planning absolutely matters. If you sell into manufacturing, field services, or any environment where reps physically visit sites, geography plays a real role. Travel time, proximity and face-to-face access matters - I’m not arguing that. But SaaS is a different world. Most selling happens online. Buyers evaluate software from wherever they sit and geography tells you NOTHING about how a buyer communicates, what they value, or how they make decisions. Yet companies continue to assign accounts based on maps as if state lines guarantee fairness. They don’t. Some regions will always be richer. Some will always be slower. New York will never resemble Arkansas. Drawing neat borders has never solved performance gaps in SaaS. The real driver of performance is something leaders rarely sit with long enough: how well each rep’s communication style, natural tendencies, and persona align with the buyer environments they’re selling into. If you have ten reps, this is the part you cannot skip. You must understand, with intention: — Which reps are analytical and naturally align with analytical buyers. — Which reps are outgoing and relational, and build trust faster in conversational environments. — Which reps are more reserved and thrive with buyers who prefer structure and detail. — Which reps are fast-paced and comfortable in quick decision cycles. — Which reps need deeper, steadier conversations to build long-term trust. — Which reps handle multiple stakeholders with ease versus those who perform best with focused one-on-one relationships. — Which reps align with rigid, formal communication norms versus more fluid, exploratory ones. This is not optional work. If you skip this, no territory model will ever feel fair or perform well, because you’re matching accounts to locations instead of matching accounts to the actual capabilities of your reps. When you allocate accounts based on communication fit and persona alignment, everything changes. The conversations feel smoother. Trust builds faster. Reps operate with more confidence because they’re selling into environments that make sense for how they naturally work. You get more predictable performance without changing your headcount or your product. This is why the territory debate in SaaS needs to end. SaaS doesn’t have a geography problem. It has a fit problem and once you solve for fit, the map stops mattering.

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Your SDRs move slow. Your market doesn’t. In 2025, sales teams win with agility. Markets shift. GTM strategies evolve. New products launch overnight. And if your SDR team can’t keep up, your pipeline’s at risk. Bad news: Most internal teams aren’t built to move that fast. Good news: Outsourced SDRs are. Here’s why they’re built for the modern sales org: 🔄 Pivot to new ICPs without missing a beat 🚀 Launch-ready teams, no hand-holding required 📊 Real-time reporting to optimize on the fly 🎯 Performance-based models (not just warm bodies in seats) The future of SDRs isn’t in-house—it’s on-demand. Want to pick the right agency to keep your pipeline fast, flexible, and future-proof? We’ve got the guide for you 👇

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