Sales Tips. From $10m - $100m. Like, really really really good sales tips.

How do you scale a sales team from “just trust us” to a public-company powerhouse? It’s not just about hiring more reps or tightening the pitch deck. It’s about building systems, aligning teams, and turning early intuition into repeatable success—without losing the spark that got things moving in the first place. In this episode of The Orita Podcast, Aaron Schwartz is joined by three go-to-market leaders who helped scale Klaviyo into a category-defining company: Sean Marshall (now co-founder of Copley), Pat Makridakis, and Matt Virzi. They dive deep into what it takes to scale sales from startup to IPO-ready—covering sales process, team structure, customer success, compensation, and the underrated power of curiosity. Whether you're hiring your first AE or rethinking your post-Series B GTM motion, this one's packed with hard-earned insights. They unpack: Scaling sales orgs without bloating headcount Why storytelling is 90% of the job in early-stage sales The power of partnerships (and why Klaviyo doubled down) How to create a high-signal feedback loop between sales, CS, and product The unsung role of customer success in driving long-term revenue 👥 Meet the guests: Sean Marshall / Copley Pat Makridakis / Klaviyo Matt Virzi / Klaviyo 🎧 Chapters: [02:38] Career Paths in Sales: Lessons from the Journey [05:36] How Enterprise Sales Has Evolved (and Why It Matters) [09:36] Understanding What Today’s Buyers Really Need [12:41] Adjusting to a New Role: What No One Tells You [14:33] Why Sales, Product, and CS Need to Work Together [18:47] Curiosity as a Core Skill in Modern Sales [22:38] Scaling Sales Without Losing What Works [29:12] Sales & Customer Success: Aligning for Growth [33:59] Early-Stage Compensation: Getting It Right from the Start [37:31] Building Pipeline: What Works at Different Stages [42:53] Tapping Customer Relationships to Drive Growth [47:26] Advice for Founders and Buyers Navigating Growth 🌐 Check out orita.ai for more episodes of The Orita Podcast—where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by Aaron Schwartz, co-founder and co-CEO of Orita. Orita uses machine learning to help brands send smarter, more profitable marketing—by figuring out who actually wants to hear from you and when. If you’ve got a customer list, this show is for you. Whether you’re deep in Klaviyo flows, thinking through supply chain strategy, or just trying to make your paid media budget stretch a little further, we’re here to help you learn from the people building some of the most resilient and resourceful brands and agencies out there. 🔗 Connect with Aaron on LinkedIn   / aaroncharlesschwartz