Dear SaaStr: What’s Really Changed in GTM in 2026?
Dear SaaStr: I run revenue at a B2B company doing about $40M ARR. My playbook is basically the one I built in 2021 and 2022, and it’s working worse every quarter. What’s actually changed in go-to-market, and what should I be doing differently? The ICONIQ...
What A New VP of Sales Needs To Be Doing Their First 2 Weeks
Dear SaaStr: What Should The First 2 Weeks Look Like For a New VP of Sales? The first two weeks for a successful VP of Sales in a B2B company should be laser-focused on understanding the business, the team, and the customers. All three. Here’s what they should...
The Top 15 Questions to Ask a VP of Sales During an Interview (Updated for 2026)
One of the classic original SaaStr posts was on the Top 10+ Questions to Ask a VP of Sales Candidate. I updated it in 2025. I’m updating it again for 2026, because the world has changed even more. We’re now in a world where AI agents handle a meaningful...
5 Simple Tips to Quickly Improve Sales Performance
Dear SaaStr: What are the best 5 tips to improve poor sales performance? If you've never listened to your sales reps' calls, Especially the ones that are mediocre performers, You'll often be shocked what you hear. — Jason ✨👾SaaStr.Ai✨ Lemkin...
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...
The #1 Mistake I See Founders Make When They Hire Their First VP of Sales
I'd say about 66% of founders step back from sales when they hire a VP of Sales 95% of the time, it backfires You don't get that time back. You just use it in different parts of the sales process. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) May 27, 2026 So...
The One Secret Tip To Hiring a Great Sales Rep (In The Early Days)
We’ve written this point before, embedded in other posts. We’ve talked about it in many presentations. But it’s time to call out One Simple Hack to getting sales going in your B2B start-up, in the early-ish days. One of the best there is in B2B....
Dear SaaStr: How Do The Best Sales Leaders Retain Their High Performers?
Dear SaaStr: How Do The Best Sales Leaders Retain Their High Performers? A few ways I’ve observed that the best sales leaders retain the best: They promote the best. You can’t promote everyone, but you can almost always promote your best. The fastest you...
That First Magical Sales Rep. The AI Era Edition.
A while back on LinkedIn and Twitter we had over 200,000 views and engagements on a quick post on “The Magical Sales Rep”, and another 500+ likes on a follow-up. It’s worth a deeper dive. Especially now in 2026, where the role of that first rep has...
Our AI VP of Marketing Updates Our Revenue Forecasts in Real Time, Without Bias. That Alone is Magical.
If you haven’t heard of 10K: it’s our AI VP of Marketing at SaaStr, built on Replit. We tried to buy something that did what we needed — an AI agent that could actually orchestrate marketing, not just write mediocre content — and couldn’t...
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...
Stop Discounting. Start Deploying. The New Way to Close Deals in B2B + AI.
We’ve all been there, multiple times. It’s the end of the quarter. The deal is close but not closed. And the sales team pulls out the oldest trick in the book: “We’ll give you a discount if you sign by Friday.” It works sometimes. But...
Dear SaaStr: I’m a Seed Stage, First Time VP of Sales. What Should I Do To Be Successful?
Dear SaaStr: I’m a Seed Stage, First Time VP of Sales. What Should I Do To Be Successful? First, congrats. That said, I have to give you the hard truth before the playbook: most first-time VPs of Sales hired at seed stage fail. Not because they’re bad....
Dear SaaStr: When Does It Make Sense to Price Low in the Market?
Dear SaaStr: When and how should SaaS startups offer reduced pricing vs the competition? For most B2B apps, you want to at least start with “just right”, Goldilocks pricing: #1. Too high a price, and you start to add friction to the sales process. Deals take longer,...
Founder SaaStr
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