Dear SaaStr: What remarks have a salesperson said to you that lost them the sale? A quick list here: “You are wasting my time”. I don’t think this was meant to be said aloud, but many B-tier reps say and think this all the time. No. A prospect’s time is always...
So we’ll have ~20 of the latest AI start-ups from YCombinator at a special YC Demo Pod area at 2025 SaaStr Annual! Come meet them (and also watch 100+ present live at our first AI Demo Stage) at 2025 SaaStr Annual, May 13-15 in SF Bay!! Here’s more on a...
So per Forbes for the first time there are over 3,000 Billionaires in the world. Tech is heavy on the list, and #1 is Elon Musk. When I started in SaaS, it was tough to imagine many B2B billionaires, as most SaaS companies were lucky to IPO at a $1 Billion...
Dear SaaStr: One of Our Most Respected Team Members Quit and Folks Are Leaving. What Do I Do? Promote someone great that everyone respects into a leadership role. Right now. This is really the only answer I’ve seen to this situation. We’ve all been in it at least to...
So Harry Stebbings kicked off a new Live 20VC format: “The Daily Deal” and I was lucky enough to serve as co-host! We did a great live deep dive, together with the CEOs of Moveworks (just acquired by SeviceNow for $2.8 Billion!) and Cerebvs (AI...
So if you are incredibly good at VC, you can make a lot of money. More on the math here. If you own 20% of a Decacorn ($10B), then the fund makes $2 Billion, and the partners typically keep 20% of that, or $400m. And split it up. The math isn’t quite that...
Dear SaaStr: What Are Simple Hacks that Salespeople Use to Confuse Customers? Well I’m not sure confusing customers so that they buy works, but the one tactic that does is FUD. Fear, Uncertainty and Doubt It’s the process of finding weakness in your competitors, and...
So Freshworks started off as a low-end Zendesk competitor (Freshdesk), but relatively early expanded into a broader suite of related products for service and support, and most of its growth today is fueled by its lower-end competitor to ServiceNow, it’s...
Dear SaaStr: How Long Should You Give a New Sales Rep? The tough truth is from 0.5–1.5 sales cycles. Sales is tough. It’s a lot of Nos to get to a Yes. And while sales is pretty similar in SaaS at a given price point / ACV, different products are still different to...
No one has a true crystal ball when it comes to Cloud spend in the coming years, but the leaders have a lot of data. Thoma Bravo is one of them. It’s the #1 Private Equity firm for B2B and SaaS companies and it surveyed 501 Cloud and SaaS buyers. Here’s...
Sam Blond and Jason Lemkin joined together for a live SaaStr Workshop Wednesday looking at what has and what hasn’t changed in 2025 in GTM in general and in the age of AI. They did a deep dive looking at top learnings not just from their own ecosystems, but from...
Dear SaaStr: What Are The Top 5 Mistakes Founders Make With Their VC Investors? In rough order: #1. Hiding Important Things. VCs are wired to take bad news. But not for it to be thrown at them at the last minute: If Times Are Tough — Don’t Hide. Be...
So this year’s SaaStr Annual May 13-15 in SF Bay is going to be bigger, better and even more AI than last year. SaaStr AI is the theme (not that original I know but), and roughly half our content will be on the intersection of B2B and AI, and half on GTM in...
At the heart of almost every great piece of software with an ACV of >$50k is a great dashboard How good is yours? — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) March 30, 2025 Sales still gets all the attention in SaaS, but the best investment you can...
Dear SaaStr: How Long Should a Sales Funnel Take from Start to Close? It depends on your deal size, target customer, buyer, and sales process. There’s no one-size-fits-all answer … but I can give you some benchmarks based on SaaS deal sizes and sales cycles: 1....