Dear SaaStr: What’s a Fair Amount of Founder Secondary in a Series B VC funding round?
Dear SaaStr: What is considered a fair or happy medium secondary amount for the founders to take off the table at a Series B VC funding round? Secondary sales done right truly align founders and the company and incent them to go long. See Brian Halligan’s (co-founder...
Founders Are Coming Back to Run Their Pre-AI B2B Companies. Because It’s The Last Stand.
I’m seeing more and more founders come back to run their pre-AI B2B companies. Not because the board panicked over a bad quarter. Because it’s The Last Stand. The pattern shows up at companies big enough to have a base that sustains them and not agentic...
After $2m in ARR — Start Specializing Your Sales Team
There’s a set of questions I get asked all the time: Should you pay sales reps on renewals? Should you pay sales reps on upsells a long time down the road? Should you pay sales reps on … ? I am a huge proponent of paying sales professionals well. But for...
Dear SaaStr: What Do You Have to Get Right in a Start-Up?
Dear SaaStr: What Do You Have to Get Right in a Start-Up? So many folks I meet want to start a start-up. They have an idea they are passionate about. They’ve worked under a great CEO, and they’re ready — they think — to do it on their own...
Dear SaaStr: Should I Send My Pitch Deck to Any VC Who Asks for One?
Dear SaaStr: Should I Send My Pitch Deck to Any VC Who Asks for One? Look every investor is different But for me at least, Send The Deck Don't fight it. Don't ask for 20 minutes first. Don't say it's better with a live demo first. Decks may seem...
Dear SaaStr: Why Do Many Startup CEOs Quit After Their Companies Are Acquired?
Dear SaaStr: Why Do Many Startup CEOs Quit After Their Companies Are Acquired? Five reasons: First, it’s very difficult for most founder-CEOs to work for someone else. They generally don’t mind working with others. They don’t even need to be “the boss”. But being told...
The Top 5 Reasons I See CROs Flame Out
I saw about 10 CROs leave or get fired the past 12 months across the startups I work with or have invested in at SaaStr Fund. That’s a lot. That’s actually a ton. It may be a record. I suspect it is. AI is the root cause of some of it. As many startups...
Dear SaaStr: How Long is a Venture Round Supposed to Last?
Dear SaaStr: How Long is a Venture Round Supposed to Last? I think like many venture axioms, founders get often get bad advice here out of good solid rules. The classic rule was “18-24 months”. In boom times, it’s still true … it’s just...
A Simple 4 Part Test to Know If You’ve Hired the Right VP
Did you hire a good enough VP? 4 part test: – who great did they hire in the first 60 days?– did their #1 key metric improve?– did they take part of the job off your plate?– does the team believe? If they don't pass the 4 part test, they...
Dear SaaStr: How Do You Build a Real Exit Strategy?
Dear SaaStr: How Do You Build a Real Exit Strategy? First, bear in mind acquisitions are relatively rare. The vast majority of startups will never get one strong acquisition offer. Still, it’s not random. I’ve been through it twice as a founder and about...
Dear SaaStr: Our VC Is Encouraging Us to Hire Aggressively and Increase the Burn Rate. Should We Listen to Them?
Dear SaaStr: Our VC Is Encouraging Us to Hire Aggressively and Increase the Burn Rate. Should We Listen to Them? In my experience, about 66-70% of the time this is bad advice, especially if it is coming from a Very Large VC. Not always. But more often than not. Why?...
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.
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 —...
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...
Founder SaaStr
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