Dear SaaStr: I’ve Hired 2 SDRs. Can I Hire an AE to Manage Them?
Dear SaaStr: After closing a few deals myself as a founder, I hired 2 SDRs and closed some more. Should I hire an AE to take over the SDRs and close or a VP of sales? Try to find a VP of Sales now, and try to hire an AE now. You probably will find the solid AE...
Dear SaaStr: How do VCs Really Feel About Founder Salaries? I Was Told That a General Rule of Thumb is 75% of Market
Dear SaaStr: How do VCs Really Feel About Founder Salaries? I Was Told That a General Rule of Thumb is 75% of Market The 75% Rule once you are VC Funded for more than a few million dollars is a good one. But if you raise less than that — 75% may well be too...
The CEO Never Gets to Step Away From Sales
"The #1 mistake founders make when they hire their first VP of Sales? Or even just their first sales rep? They step back from sales. No. You don't get that time back. It's just what you do in sales, changes." pic.twitter.com/wwUzRvrbt0 — Jason...
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...
Dear SaaStr: Should You Ask a Prospect What Competitors They Are Looking At?
Dear SaaStr: Should You Ask a Prospect What Competitors They Are Looking At? Yes. And in 2026, more than ever. You’ll find 90% of the time you’ll want to not just tell a prospect who you are competing with, but do so aggressively. And box the competition...
Dear SaaStr: If I Whitelabel My B2B Product, Will it Hurt Me on Branding?
Dear SaaStr: If I White-label my B2B product, will it hurt me on branding my own company? Just do it. If it’s easy to do. Lots of folks agonize over white-labelling. The brand benefits will go to my partner, not me. I’ll be valued less. Etc. etc. But bear in mind a...
Dear SaaStr: What’s the #1 Way I Can Accelerate My Career Growth?
Dear SaaStr: What’s the #1 Way I Can Accelerate My Career Growth? My uber-learnings: Find the best boss you can; and Take on every initiative, project, task, and endeavor you possibly can from her. And work for them for a while. Long enough to get promoted once,...
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: What Are Some Signs That Your B2B Marketing Programs Won’t Scale Well?
Dear SaaStr: What Are Some Signs That Your B2B Marketing Programs Won’t Scale Well? The #1 flag your marketing efforts aren’t working is that you are spending too much — but importantly, in the aggregate. Don’t overindex on any individual campaign...
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...
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...
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: What Is A Good Demo Conversion Rate for a SaaS Startup?
Dear SaaStr: What Is A Good Demo Conversion Rate for a SaaS Startup? 10%-20%. If fewer than 8%-10% or so of your demos convert to paid customers, you’ll start to burn out your sales team. Because they generally need to close 10-15 deals a month to eat (more for SMB,...
Dear SaaStr: How Do You Compensate Reps on Multi-Year Deals?
Dear SaaStr: How Do You Compensate Reps on Multi-Year Deals? In the early days, when Cash is King, pay the sales reps a full commission on all cash paid up-front. It’s what I did. 95% of the time, this is what you want to do. As as a SaaS founder, I paid...
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