Dear SaaStr: As a Founder, What Will I Learn Getting More Involved in Sales?
Dear SaaStr: I’m Pretty Hands Off on the Sales Team. What Will I Learn Getting More Involved in Sales? The most important thing that you will learn is how businesses truly scale on the revenue side. You may think you know this intuitively, but you don’t:...
The Top 10 Mistakes Folks Make Hiring Their First Sales Team (Updated)
Times for many are so different in B2B than they used to be. For those with AI tailwainds, growth is like nothing we’ve ever seen. For those without, it can seem like everyone wants to downgrade or cut. For some, it’s somewhere in the middle. It can seem like...
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...
To Really Scale, You Need $1M on Your Balance Sheet for Every $2M in ARR
"To really invest in your team, product, etc. you need at least $1 on the balance sheet for each $2 in ARR. At $20m ARR? You need $10m in the bank to make the hires, burn the tokens, etc. to really get to the next level. Below that … you hesitate."...
Dear SaaStr: How Does a Sales Rep Truly Add Value?
Dear SaaStr: Do salespeople add to the value received by customers? They do in the enterprise. At least the good ones do. That’s what a lot of founders miss if they haven’t worked with great mid-market and enterprise sales execs before. Let’s break sales down into 2...
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...
Everyone Ends Up With a Sales Team. Even in the AI Era. The Team Just Scales Later Now. See, E.g., Replit, Gamma, Lovable, Anthropic, etc.
Amjad Masad, founder and CEO of Replit, posted the other day: “I thought I hated sales culture. By the end of this year, more than half my company will be salespeople.” He goes on: for most of the last decade he was a typical tech guy. Build a good...
Top 10 Mistakes I See New CROs and VP Sales Make The First Week on the Job
"The top mistakes CROs make when they pick their next role: #1. Needing to be too passionate about the space#2. Don't do enough diligence on fit for their skills#3. Don't listen to enough calls before they start" pic.twitter.com/XaVCGouUnJ —...
The 0% Quota Club (And Why the Same Mediocre Rep Hits 70% at One Company and 0% at Yours)
In sales orgs with extreme product market fit, tight processes, and substantial support … medicore sales reps can often hit 50%-90% of quota. Sometimes even more for stretches In sales orgs without all 3, they often hit 0% of quota — Jason ✨👾SaaStr.Ai✨ Lemkin...
Beware the “Mediocre Recycled.” The Zombie Executives of B2B + AI.
So I wrote a version of this post a while back, and it struck a chord. A lot of founders reached out and said some version of “I just hired one of these.” Or worse, “I’ve hired three.” But I’m updating it now because I’m...
12 of the Most Common Mistakes Scaling Your First Sales Team
Dear SaaStr: What are the most common mistakes founders make hiring their first real sales teams? A few key mistakes I see start-ups making > 50% of the time: Hiring Early Reps (#1 – #3) That You Personally Wouldn’t Buy From. Don’t hire someone with the...
The Top 12 Sales Lessons From SaaStr AI 2026: Anthropic, Gamma, Owner, Stripe, Salesforce, Vercel, Replit and Monaco
The sales and GTM sessions at SaaStr AI 2026 in San Mateo was all about where to take agents next. No one was still debating whether to put agents in the revenue org. They had already done it, and they brought the war stories. What broke, and what they would do...
How a Mediocre Sales Team Loses You Deals. Ones You Could Have Won
A vendor reached out to me last week for fund administration for SaaStr Fund. We are genuinely in the market for a vendor and it’s a $100k+ a year potential client. This should have been a real shot for them. It started on LinkedIn, where they reached out. I...
Sales Rep Annual Quotas in 2026: What High Performers Are Actually Carrying: $750k for SMB, $1.35m for Mid-Market, $2.25m for Enterprise
ICONIQ recently released their 2026 GTM benchmark report, and it shows that overall sales quotas and processes are similar to the pre-AI era. Just … ramped up. Top-quartile enterprise AEs are now carrying $2.25M annual quotas Mid-Market is $1.35M SMB is $750K...
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