Dear SaaStr: What’s The Best Way to Set Targets for the Sales Team?
Dear SaaStr: What’s The Best Way to Set Targets for the Sales Team? First, I try to model 3 overall plans for the year: C-90, C-60, and C-10, not just for the sales team, but the whole company. The C is for “Confidence”. The odds you think you...
Events Work. Events Are Back. But Are They Worth the Big Expense?
"Field marketing like events do work. They are magical. But only if you are great at them. At SaaStr itself, I saw one competitor close $700k in revenue week after our European event. And a very similar competitor close … $0."...
The #1 Reason CMOs Fail
"Too many CMOs and CROs come into a new role and just run the playbook that worked at their last role. You have to start by improving the playbook that's currently working. Not running your prior one." with @kippbodnar pic.twitter.com/Sf0nAyIbyI —...
Dear SaaStr: How Do I Deal With Investors That are Unhappy With The Company?
Dear SaaStr: How Do I Deal With Investors That are Unhappy With The Company? Be transparent. And show them an honest, data-driven path to a better future. First, investors get most upset when founders hide things. And founders tend to hide things more when times are...
9 Signs a Startup Isn’t Going to Make It with SaaStr CEO Jason Lemkin
In a recent Workshop Wednesday, SaaStr Founder and CEO, Jason Lemkin sat down to discuss 9 signs a startup isn’t going to make it.
Hiring a Strong New VP? Let Them Pick Their Right Hand Person
So there’s a mistake I see a lot of founders make again and again, especially when cash is tight. In fact, these days cash is tight for most, even if you’re at $20m, $50m, $100m ARR, since everyone’s trying to get more efficient and profitable. And the mistake they...
6 Key Signs a VP of Sales Can’t Scale Beyond $5m-$10m ARR
The best VPs can recruit in ways I barely understand You need someone for a key role? They somehow have 2-3 strong candidates in a week or two This is so, so hard But the very best VPs make it somehow look almost effortless It's also the only way to scale —...
Your VP Sales Has a Sales Quota. Your VP Marketing Has To Have a Quota, Too.
One of the first iconic SaaStr posts was Hire the Right Type of VP Marketing or You’ll Just End Up With a Bunch of Blue Pens with Your Logo On Them. The basic idea was to help folks who haven’t hired a VP or Director of Marketing hire the right one for a...
Don’t Let Them (Your Best Employees) Go
When you see Founder Mode from a non-founder When you find a VP, an exec, that actually cares as much as a founder, or almost as much … Promote them fast. ASAP. Double their equity. And … never let them go. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) May 29, 2026 It...
Dear SaaStr: What’s the #1 Mistake New Sales Leaders Make?
Dear SaaStr: What’s the #1 Mistake New Sales Leaders Make? Let me just summarize my #1 observation here: the top mistake first-time sales managers make is recruiting. In that — they can’t do it. They can’t recruit great reps. They can recruit some mediocre...
High NRR is Magic. It Can Also Hide a Lot of Problems.
Having high net revenue / dollar retention is the magic of B2B. If you have 120% NRR, you double in less than 5 years, even with no new customers. Above that, you really get into magical compounding growth. But here’s the 2026 reality check: high NRR has gotten...
Why It’s Year 3 When You Lose Your Larger Customers (And in The AI Age, It’s Becoming Year 2)
Recently I was catching up with a good friend who used to be CEO of an enterprise-y B2B social networking company. The usage and engagement numbers of his business were just awful. Customers bought because they thought their organizations needed this functionality,...
What to Do If Your Business Decelerates
A top B2B VC said to me back in the day: “Once a B2B business decelerates, it becomes almost hopeless. No one will buy you, fund you, or join you.” That quote was true then. It’s only gotten more true in 2026. The good thing about B2B is the revenue...
Should You Fire an OK-but-Not-Great VP of Sales? Probably Not (Updated)
I wrote a version of this post some time ago, and I think it’s really one of the most important posts on SaaStr of all time, so I wanted to update it, especially in these times of more scrutiny and less capital. Because many of you are wondering … should...
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