If Times Are Tough — Don’t Hide. Be Present.
What I see CEOs at struggling start-ups do: – Go dark– Hide– Lash out– Tweet about lots of things non-work– Invest time on tiny expenses– Argue internally What should do: – Be Present– Be Honest– Be the Rock–...
Dear SaaStr: What’s the #1 Most Important Thing To Look For In Your First Sales Rep?
Dear SaaStr: What’s the #1 Most Important Thing To Look For In Your First Sales Rep? The #1 most important criterion for your first 2 reps is: would you buy from her? For real? Would you truly, 100%, buy your own product from them? 98% of the reps you interview …...
Faster Closes. Shorter Contracts. Leaner Teams. The Top 10 Learnings From the Latest ICONIQ GTM Report.
ICONIQ just published their State of Go-to-Market in 2026, based on a January 2026 survey of GTM executives at 150+ B2B + AI software companies. The data is always good, Iconiq invests at the growth state in a large cross section of the best in B2B + AI. Here are the...
Five “Cons” To Adding a Free Edition
Dear SaaStr: Is There Any “Con” In Giving Our Sales Tool For Free to Early-Stage Startups? Free can absolutely work. Done right, it’s built some of the biggest companies in B2B + AI: ChatGPT. Claude. Cursor. Slack. Zoom. Canva. Notion. Figma. Almost...
Dear SaaStr: At What ACV Can We Afford a Sales Team?
Dear SaaStr: At What ACV Can We Afford a Sales Team? The short answer hasn’t changed much: it’s still tough to afford a human sales team below $299 a month / $3k a year ACV. At least in the U.S. and Western Europe. The math just doesn’t bend enough....
Dear SaaStr: If We Have Two Overlapping Products is it Better to Have One Sales Team or Two?
Dear SaaStr: If We Have Two Overlapping Products is it Better to Have One Sales Team or Two? It’s almost always better to have different sales teams handling different products Why? If for no other reason — Incentive Alignment. Sales reps work on commission, and they...
The #1 Conceit in B2B at Scale: Masking a Slowdown in Net New Customers
Why Covering Up Declining Customer Growth is the Beginning of the End I’ve seen this movie play out dozens of times now across hundreds of B2B companies. And it almost always ends the same way. The #1 conceit in B2B — the thing that kills more companies than bad...
Dear SaaStr: How Do You Change the Price of Your SaaS Product Without Upsetting Existing Customers?
Raise prices on existing customers,Doesn’t help if you are growing quickly. Just makes them unhappy. Raise prices on new customers,Forces you to deliver more value. Often makes everyone more happy. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) April 7, 2022 Dear...
Dear SaaStr: What Are Some Best Practices for Selling a New Product Into Existing Customers?
Dear SaaStr: What are some best practices for selling a new product/service to your existing SaaS clients? First, make sure your NPS is high. And drive it even higher. Here’s the bottom line: if your NPS is say > 40 or so, a significant portion of your customers...
The CEO of An AI Agents Company We Really Love Asked Why We Didn’t Pick Them. Here’s the Honest Answer.
The CEO of an AI Agents company we genuinely admire reached out recently and asked why we didn’t select them as a vendor. It was a fair question — they have a great product. The honest answer? Their VP of Sales argued with us. Wouldn’t do any work up...
If AI GTM Tools Were Half as Good As Cursor or Replit, It Would Be a Different World Today. They Will Get There.
We’ve been running AI GTM agents for almost a year now. We use Artisan for outbound, Qualified (now Salesforce) for inbound, Agentforce for Salesforce-native outreach, Delphi for Digital Jason. We’ve sent 20,000+ AI messages and generated over $2M in...
Should You Pay Reps More For Deals They Hunt Themselves? Sometimes. Here’s When.
Dear SaaStr: Should sales reps be compensated differently based on how much prospecting they do? For example, if all of their leads come inbound (without effort on their part) should they receive a lesser % per deal vs a rep that prospects for their own leads? It...
Dear SaaStr: Should We Pay Our Sales Reps on Renewals?
Dear SaaStr: Should We Pay Our Sales Reps on Renewals? Simple answer: most don’t. You can, especially in the early days. But very few SaaS companies pay sales reps on renewals as they scale. And you can definitely pay on upsells and account expansion. Longer...
Dear SaaStr: Is It Worth Working as a Sales Rep?
Dear SaaStr: Is It Worth Working as a Sales Rep? Absolutely. Being a sales rep is the hardest job that almost anyone can get and at least try to do. But boy, you will learn. You will learn: How to hear “No” 100 times in a row. If you can turn 100 “No’s” into 1–2...
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