Sales isn’t going anywhere in the Age of AI. OpenAI has a big sales team, Windsurf does, Anthropic has a great one. It’s just … so many of the AI leaders seem to be doing it with less GTM headcount. Especially the next generation of them:...
When AI Resurrects “Dead” Leads: A SaaStr Case Study on What Sales Teams Miss, But AI Can Catch Our sales AI reactivated 4 leads in past 48 hours that our human sales team said were dead / not-interested All took a meeting asap Something to reflect on...
How Canva’s CCO Built a $7B Enterprise Motion While Preserving PLG Culture Rob Giglio, Canva’s Chief Customer Officer, shares the playbook for scaling from 170M to 230M monthly active users while building enterprise sales without compromising company...
The Enterprise-Grade Platform That Makes AI Voice Agents Actually Work at Scale We’re proud to announce that Syllable is returning as a partner for SaaStr Annual + AI Summit 2026, following their tremendous success and impact at our 2025 event. The Bottom Line:...
Dear SaaStr: What Are The Top Worries Founders Have As They Start to Scale? B2B SaaS founders tend to share a lot of common concerns, especially as they navigate the different stages of growth. Here are some of the big ones I’ve seen repeatedly: 1. Customer...
Three Big Things This Week: Daniel Gross & Nat Friedman walked away from a $1.1B fund (already 4x’d) to join Meta – signaling the biggest talent war in Silicon Valley history “Triple-triple-double-double” SaaS growth is now boring –...
Here’s a concise tweet summarizing the Olo vs Toast analysis: 🧵 Olo vs Toast: A $2B vs $25B tale of strategic choices Both restaurant tech companies IPO’d in 2021, but chose radically different paths: 🎯 Olo: Enterprise-first (300k locations) → Higher...
After less than 30 days with our AI SDR, we became the highest response rate on our AI SDR platform. #1. Here’s what actually works — and what doesn’t. _______ We’ve all gotten that terrible AI SDR email. You know the one: “Hey [FIRST NAME], I...
Dear SaaStr: What Does the Day-to-Day Look Like For a Customer Success Manager? The day-to-day of a Customer Success Manager (CSM) will vary depending on the company’s stage, customer base, and ACV. The bigger the startup, the more it’s about process vs. just getting...
TL;DR: NVIDIA just became the first company in history to hit a $4 trillion market cap. Starting from a $563M IPO in 1999, that’s a mind-bending 693,574% return. For SaaS founders, NVIDIA’s journey offers critical lessons about platform strategy, timing...
