7+ Tips On How To Build Your First Sales Team. When You Have Zero Experience Building One.
Dear SaaStr: How do you structure a sales team … when you’ve got zero experience doing sales? Well, first go get some experience with sales. 🙂 At least, close the first 10 customers yourself. If you don’t, you’ll never have any idea how to do it. And the odds...
The B2B Category the Markets “Hate” the Most Today: GTM
Salesforce agreed the other day to buy Braze for $5.66 billion, 6.8x trailing revenue. In most of B2B that price would be unremarkable. In go-to-market software it’s a 58% premium, because Braze traded at 3.7x on Monday. I pulled the multiples for the public GTM...
Annual Contracts: Maybe Not All They Are Cracked Up To Be
Annual contracts seem so great. VCs love them, and they do seem to reduce churn. Seem to. In fact, when CROs struggle to hit a plan, they often want to push customers onto annual contracts. That and pricing increases are classic go-to moves. I’ve long been a...
20VC x SaaStr: Anthropic’s S-1 Shows $16.3B in First-Half Revenue, Microsoft Offers Buyouts to 27% of Its Staff, and Chinese Open-Weight Models May Be Done in the US
Plus Broadcom backstopping Anthropic’s chip debt, Meta’s $95B equity raise, the PHP2Shell flaws, and an IC fight over Instinct at $30B and OpenAI at $1.25T This week had one story that mattered more than everything else combined: Anthropic finally filed...
5 Interesting Learnings from Guidewire at $1.24 Billion in ARR: A $1.7 Billion AI Acquisition, Its Lowest Churn Ever, and 10x ARR for a 25-Year-Old System of Record
Guidewire sells core systems to property and casualty insurers: policy, billing, and claims. It was founded in 2001. Its buyers are some of the slowest-moving in B2B. In a year when the market repriced anything that looked like legacy software, it still trades at...
Sponsor SaaStr AI Annual 2027. Walk Out With 85+ Customer Meetings Set.
A few months after SaaStr AI Annual 2026, someone asked on LinkedIn how many leads sponsors got from the event. Steve Burton, CMO of Aurasell, answered in one line: “Don’t count leads, but we booked 85 meetings on the calendar.” Aurasell’s CMO...
Databricks CRO Ron Gabrisko: 5 Interesting Learnings on Selling at a $190B AI Company: Flat SDR Headcount, 6-10% Reply Rates, and Free Seats That Unlocked Consumption
Ron Gabrisko joined Databricks as CRO when it was doing under $1M in ARR. Databricks is now a $190 billion company doing $7B+ ARR growing at a pace like we have never seen before. Ron sat down with Sam Blond, co-founder of Monaco and former CRO of Brex, on the SaaStr...
10 Months Into AI for GTM That Actually Works: The CRO Matters More Than Ever. Every Other GTM Role Is in Flux.
We are about 10 months or so into AI for go-to-market that actually works: agents running real motions in production, booking real meetings and closing real dollars. In that time, agents have absorbed much of SDR, first-line support, a growing share of CS, and big...
The $300 Billion Software Debt Wall: The Big B2B Defaults Unfortunately Haven’t Even Started Yet
The big defaults for software debt … are unfortunately yet to come @wsj “Solera, a maker of software for vehicle maintenance, has about $8 billion in loans coming due in 2028 and 2029. Vista Equity Partners, which acquired the company in 2016, had planned an initial...
Dear SaaStr: How Do I Know If My New VP of Marketing Is Going To Make It?
Dear SaaStr: How Do I Know If My New VP of Marketing Is Going To Make It? You’ll know pretty quickly if a new VP of Marketing is going to make it, or not. The best ones deliver real results fast, and there are clear signs to watch for in the first 30-90 days....
Two AI Agents Wiped Critical Data at SaaStr. Both Times, a Copy Nobody Planned Is What Saved Us. It Will Happen To You, Too. Plan For It.
We run SaaStr with three humans and 20+ AI agents in production. In the last few weeks, two different agents destroyed something we can’t run the business without. Both times we got it back within an hour, and both times the copy we restored from was one we had...
Sumble: Why 80% Accurate Data Turns Into 33% Accurate Data by the Time Your Agent Uses It, and How Nooks Found 700 Accounts It Didn’t Know About
Amelia called Sumble the best company you probably haven’t heard of yet. Its customers include Snowflake, Databricks, Figma, Wiz, Monaco, and a long list of AI companies like Baseten, Vercel, Modal, and CodeRabbit. SaaStr has been running it for the last six to...
Dear SaaStr: How Many Sales Reps Do I Need?
Dear SaaStr: How Many Sales Reps Do I Need? More than you probably would think. You can back into how many sales reps you’ll need in SaaS: First, figure out how much sales-driven revenue you need to close in the next twelve months. Because that’s more than now....
5 Interesting Learnings from Anthropic’s S-1 at $16.3 Billion in Half-Year Revenue: 900% NRR, $6.6M in Revenue Per Employee, and a 10% Adjusted Operating Margin
Anthropic filed its S-1 this morning. It plans to list its Class A common stock on the Nasdaq Global Select Market under the symbol “ANT,” and the share count and price range haven’t been set yet. Largest IPOs in History, by Deal Size 1. Anthropic...
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