5 Interesting Learnings from Chime at $2 Billion in ARR
So Chime is ready to IPO, and while it’s not SaaS or true B2B today, there are enough interesting lessons for us to learn from. As a “prosumer” app there is overlap for SMB and freemium B2B apps. The metrics are very strong: $2B ARR (run rate...
The 40% Problem: Do Your Sales Reps Really Cover All Their Accounts? And Is AI The Answer? With Yamini Rangan, CEO HubSpot
There’s a brutal truth about B2B sales that most founders refuse to acknowledge. HubSpot CEO Yamini Rangan just laid it bare at a recent conference, and it should make every SaaS leader uncomfortable. Your sales reps only cover 40% of their assigned accounts....
Dear SaaStr: Can I Buy Out My Seed VCs? We’re Doing Well But We’re Not on Venture Path Anymore
Dear SaaStr: Can I Buy Out My Seed VCs? We’re Doing Well But Not on Venture Path Anymore Look, it does happen and it’s possible. Expensify bought out Redpoint out before their IPO. Buffer did something similar. But it’s hard. It’s hard...
Thoma Bravo’s Record $34.4B Fundraise: Great News for B2B and SaaS Founders
Thoma Bravo’s Record $34.4B Fundraise: What Every B2B and SaaS Founder Needs to Know Very good for B2B. “The firm has invested in more than 535 software companies, and today, its software portfolio includes over 75 companies that generate approximately $30...
Gartner: Only 18% of CROs and 15% of CMOs are considered “AI-savvy” by their own CEOs.
So some of the latest Gartner data reiterates a theme from our invite-only CMO and CRO events at 2025 SaaStr Annual + AI Summit: Many CMOs and some CROs are scared they aren’t AI-savvy enough to succeed. And many CEOs feel that way about their CMOs and CRO. In...
In The Age of AI, It Just Won’t Be Enough Just To Be a “Good People Person” in Sales
The #1 objection I hear to AI in sales is that what matters most in sales in B2B and SaaS is being a “good people person”. That does matter. It matter even more in field sales, in-person sales, and true enterprise sales. But is it enough in the age of...
Dear SaaStr: What Are Good Benchmarks for Sales Productivity in SaaS?
Dear SaaStr: What Are Good Benchmarks for Sales Productivity in SaaS? Good benchmarks for sales productivity in SaaS depend on your stage, ACV (average contract value), and sales model, but here are some key metrics to focus on: Quota Attainment: A good rule of thumb...
Snowflake Buys Crunchy Data for $250m, Databricks Buys Neon for $1B. The New AI Database Battle.
Snowflake vs. Databricks: The $1.25 Billion PostgreSQL Battle for AI Agent Supremacy Brief Overview: Two data giants are making strategic moves to dominate the AI agent infrastructure market through major PostgreSQL acquisitions. Snowflake’s $250 million...
AI Startups Burn Through Cash 2x as Fast, and 10 Other Top Learnings from SVB’s Latest in Enterprise
So SVB has another deep dive out across all its enterprise software customers. Â It has at ton of great data. After diving deep into their data (covering everything from funding patterns to unicorn lifecycle management), we’ve pulled out the 10 most surprising...
Dear SaaStr: What’s The #1 Mistake Founders Make When They Start to Do Marketing?
Dear SaaStr: What’s The #1 Mistake Founders Make When They Start to Do Marketing? In B2B / SaaS, the biggest mistake most businesses make in marketing is underestimating how hard it is to get ROI—and then doing nothing. Or almost nothing. Too many founders look...
Top SaaStr Posts and Pods of the Week: The Great AI Reset, Marc Benioff on M&A and AI,
Top Posts: #1. The Bar Today for a Series B #2. The AI Wake-Up Call with Jason Lemkin: Why You Need to Move Faster or Get Left Behind #3. The 2026 Sales Team: 50% Humans, 50% AIs. All 1 Team. #4. 5 Interesting Learnings from UiPath at $1.7 Billion in ARR #5. The...
The Top 10 SaaStr Learnings from Mary Meeker’s Latest Report on AI
So Mary Meeker has been doing extremely well researched, deep analyses of internet trends since the earliest days the web took off. Â First at Morgan Stanley, then at Kleiner Perkins, and since then, at her own growth VC fund, Bond Capital. The latest one is all AI...
Dear SaaStr: What Are The Most Common Mistakes First-Time Founders Make Building Enterprise Sales Teams?
Dear SaaStr: What are the most common mistakes first-time founders make when building enterprise sales teams? The most common mistakes first-time founders make when building enterprise sales teams are surprisingly consistent. I’ve seen them over and over, and I’ve...
The Latest SaaStr + 20VC: The Brutal Math of Venture Capital — What Every B2B Founder Needs to Know
So Harry, Jason and Rory are back on 20VC to discuss the latest in tech and B2B, from why OpenAI bought iO for $6 Billion, to why YC is dominating seed, to the real bar to IPO today, and so much more: The Brutal Math of Venture Capital: What Every SaaS Founder Needs...
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