A transparent look at what’s really working in B2B content marketing in 2025 Bottom Line: While everyone’s declaring SEO dead and pivoting to AI-generated content farms, we took the opposite approach. The result? 33.6M search impressions annually, 5x growth in 12 months, and complete category dominance in B2B SaaS search. The “SEO is Dead” Narrative…
Continue Reading

From the new SaaStr “Swapping Notes” podcast series – essential listening for every B2B founder and marketing leader navigating the AI transformation The AI Marketing Revolution: Key Insights from G2’s CMO on How B2B Buying Has Forever Changed From the SaaStr “Swapping Notes” podcast series – essential listening for every B2B founder and marketing leader…
Continue Reading

Dear SaaStr: What Are The Top Red Flags for VCs When Deciding to Invest in a Startup? When VCs evaluate startups, there are definitely some red flags that can make them hesitate—or outright pass—on an investment. Here are the key factors that are often considered “bad” news: 1. Weak Founder or Team VCs invest in…
Continue Reading

Jason Lemkin joined our free, LIVE SaaStr AI Workshop Wednesday to talk about something everyone’s buzzing about but few are being honest about: vibe coding without developers. After seeing endless social media posts claiming you can “build your own HubSpot in 20 minutes” and watching the same people who used to sell get-rich-quick courses now…
Continue Reading

One of the best parts of YC Demo Day is catching up with VCs you haven’t seen in a while. And this time I several sobering conversations with top VCs that made it clear: Many VCs have now just quietly given up on their slow-growth portfolio companies. Especially the ones at $50m, $100m+ ARR that…
Continue Reading

Dear SaaStr: How Do I Build a Great SDR Team? Building a great SDR team is one of the most critical steps in scaling a SaaS company, especially when you’re selling to the C-suite or enterprise. SDRs are the engine of your pipeline, and if you get this right, it can transform your sales organization….
Continue Reading

Ramp just released its latest data on LLM Model Spend data and it shows about what you’d expect … but it also highlights the strong momentum with Anthropic. Ramp itself has crossed a stunning $1B ARR and manages billions and billions of spend: Summary & 2026-2027 Projections: Current landscape: OpenAI leads at 36.5%, Anthropic accelerating…
Continue Reading

We’re back on 20VC + SasStr with Harry Stebbings, Jason Lemkin, Rory O’Driscoll, and special guest Jeff Lawson (Founder & Former CEO, Twilio) Bottom Line Up Front Rory O’Driscoll: Tesla’s trillion-dollar pay package for Elon is a board betting everything on doubling down – they believe without him, the stock drops 75% overnight. It’s intellectually…
Continue Reading

Here’s the the reality every founder running sales, and every first time VP of Sales and sales leader learns the hard way: You can’t coach someone into being something they fundamentally aren’t. Especially a sales exec. I’ve seen this pattern play out literally 100+ times across B2B companies from Series A to IPO. Again and…
Continue Reading

Dear SaaStr: How Should I Structure the Comp Plan for a VP of Customer Success? For a VP of Customer Success, variable comp should be tied directly to measurable outcomes that align with your company’s growth goals. At $6M ARR, the key metrics to focus on are Net Revenue Retention (NRR), Gross Retention Rate (GRR)…
Continue Reading

TL;DR: Larry Ellison, founder of Oracle way back in 1977 (!), is about to become the world’s richest person, surpassing Elon Musk (at least for now), thanks to Oracle’s AI surge. Here’s what every B2B founder needs to know about this wealth flip. And what it means for your company. Oracle’s AI Bet Is Paying…
Continue Reading

The Problem Folks Don’t Talk About Enough: The Stressful Legal Micro-Dramas That Come Just as Thing Start Getting Good When you’re building your B2B startup, you’re laser-focused on product-market fit, customer acquisition, and scaling your team. But there’s a hidden tax that many founders don’t see coming until it hits: frivolous lawsuits. Here’s what seasoned…
Continue Reading

Dear SaaStr: What Are Some Red Flags in a Founder? A few: Doesn’t know the market cold. Always pass. The best founders know the market cold, even in the earliest days. Doesn’t understand or respect the competition. The best always do. Even if they are beating the competition. Can’t recruit a strong management team. This…
Continue Reading

The Numbers Don’t Lie: Founders Are Starving for Real Valuation Data Sometimes, something just clicks. And that’s our new SaaStr.ai Startup Valuation Calculator: 200,000+ valuations in just 14 days. That’s not a typo. That’s not inflated bot traffic. That’s 200,000+ founders, VPs, and startup leaders desperately trying to figure out one simple question: “What the…
Continue Reading

From the SaaStr Annual / AI Summit – How three breakout AI companies rewrote the rules of enterprise sales. And see everyone at 2026 Annual + AI Summit May 12-14 2026 and SaaStr AI London Dec 2-3! Speaker Bios Talia Goldberg – Partner, Bessemer Venture Partners Talia leads AI investments at Bessemer and has been…
Continue Reading