What a Great VP Sales Actually Does. Where The Magic Is. And When to Hire One.
In B2B, #1 most common mishire, with a bullet, is the CRO/VP/head of sales. In fact, there’s a VC saying that I used to really hate. It goes something like “You’ve Got to Get Past the Carcass of Your First VP of Sales” or “It’s...
If Your CRO, CCO or CPO Doesn’t Meet With Customers Their First Week On The Job … Move On. Apologize, But Let Them Go.
"A VP Sales, Product, Customer Success, all of them … have to meet customers their first week. They have to. Or don't hire them. You'll be surprised how many folks want to be managers, but not meet customers or do a lot of the work themselves. So...
The #1 Mistake I See Founders Make When They Hire Their First VP of Sales
I'd say about 66% of founders step back from sales when they hire a VP of Sales 95% of the time, it backfires You don't get that time back. You just use it in different parts of the sales process. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) May 27, 2026 So...
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...
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...
Dear SaaStr: What Sales Comp Plan Should I Use For Our Very First Sales Rep?
Dear SaaStr: What Sales Comp Plan Should I Use For Our Very First Sales Rep? At the end of the day you have to solve for two things: A plan that gives the reps a living, fair wage; and A plan that you know and feel is accretive to the company. Sales reps have to be...
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...
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....
The Simplest, Highest-ROI Place to Put an AI Agent Is Your Contact Me Form: 614 Meetings, $2M+ Closed, and 71% of a Month’s Deals
If you’re trying to figure out where to deploy your first real AI agent in go-to-market, start with the most boring page on your website. The Contact Me form. No one should wait days to hear back from a 21-year-old human whose job is to qualify them. And yet...
The Top 10 Mistakes People Make When Hiring a CRO / VP of Sales with SaaStr CEO and Founder Jason Lemkin
Hiring a VP of Sales isn’t new, but the conversations have evolved as the world has. SaaStr CEO Jason Lemkin shares the top 10 mistakes he sees.
Should You Hire a Sales Rep First, Or a Sales Manager?
Dear SaaStr: Should I Hire a Sales Rep First, Or a Sales Manager First? The ideal flow is: You (founder-CEO) close the first batch of customers, say the first 10 or 20. If you don’t, you’ll never really know how it’s done. Or be able to help anyone else, really. Then,...
The 9 Qualities of a Great Sales Rep
Dear SaaStr: What qualities do the great salespeople have? When I'm ready to buy, A great sales rep makes it easier. And better. And gets all my questions answered. A mediocre rep just makes it harder. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) April 2, 2022 I...
Should Your VP Sales Start Off as a Player-Coach?
The moment comes when it’s time to hire your first VP Sales. We’ve talked in the past about the 48 Different Types of VP Sales, What a VP Sales Really Does, and even given you a Script to Use When Interviewing a VP Sales. So then that time comes....
Founder SaaStr
Related Posts
Industry News
- Nvidia Opens Investigation Into Jensen Huang’s Relationship With Chinese Spy
- Musk says Grok Bot’s costs are ‘unsustainably high,’ while OpenAI admits Dots are ‘compute heavy.’ Is the personal AI agent push dead on arrival?
- Ziff Davis loses 37% of Google traffic as publishers count the AI bill
- Anthropic warns that it’s very close to RSI capability, aka self-building AI
- Cloudflare Just Had Its “Best Quarter Ever” on the Day Tech Crashed
- OpenAI Completes $11 Billion Portion of Funding at $1.25 Trillion Value
- Microsoft plans to use fewer neoclouds as AI buildout shows signs of strain
- Haircut No. 2: Anthropic IPO Talk Slides To $1.2 Trillion As AI Rout Crushes Odds Of A November Listing
- Dealroom.co | Dialpad to combine with Ada in $430M share deal, down from $1.2B peak valuation
- Toronto AI chatbot firm Ada to merge with U.S. company Dialpad in $600-million deal