Dear SaaStr: What’s The #1 Mistake Founders Make When They Start to Do Marketing?
Dear SaaStr: What’s The #1 Mistake Founders Make When They Start to Do Marketing? In B2B, the biggest mistake most businesses make in marketing is underestimating how hard it is to get ROI. So they basically do … nothing paid. Or almost nothing. Too many...
Dear SaaStr: My Top Sales Rep Made $600,000 a Year — And Just Quit! What Happened?
Dear SaaStr: My Top Sales Rep Made $600,000 a Year — And Just Quit! What Happened? Ok to some of you this will make no sense. But now I’ve seen this happen again and again, including just the other day at one of my top portfolio companies. The #1 or #2...
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...
Dear SaaStr: What Quota Should I Give to my Enterprise Sales Reps?
Dear SaaStr: What Quota Should I Give to my Enterprise Sales Reps? For enterprise sales reps, quotas typically range from 3x to 5x their fully burdened on-target earnings (OTE). This means if your rep’s OTE is $200K, their annual quota should be somewhere between...
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 Best Sales Reps Get Customers to Buy. Even When They Don’t Need to Right Now.
Dear SaaStr: Can salespeople really get customers to buy a product they don’t need right now? Yes, at least up to a point. In many ways, getting folks to buy a product they don’t truly need today is the true art of sales. If they really, truly needed it right...
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...
Dear SaaStr: As a Startup, What Are Some Effective Ways For an Underdog to Take Down Their Competition?
Dear SaaStr: As a Startup, What Are Some Effective Ways For an Underdog to Take Down Their Competition? It depends on the gap. In B2B historically, I’d argue if your competitor is larger than you, at $8M-$10M+ in ARR and growing quickly, with even reasonably...
Dear SaaStr: A Big Tech Co Launched a Competitive Product. How Can I Tell How Serious They Are About It?
Dear SaaStr: A Big Tech Co Launched a Competitive Product. How Can I Tell How Serious They Are About It? In B2B at least, I’ll give you a few metrics that are fairly reliable. The classic one still works, but in 2026 you need to layer in some new signals too....
Dear SaaStr: Should Your Ask a Prospect What Competitors They Are Looking At?
Dear SaaStr: Should Your 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...
Schmoozing Is Dead, Agents Are Hitting 120% of Humans, and Growth Is the Only Thing That Matters: 10 Things From the Closing Q&A at SaaStr AI Annual 2026
We just wrapped SaaStr AI Annual 2026, and the closing Q&A on Day 3 ended up being one of the most engaged of the whole gathering. No script, no prepared deck, just an hour-and-a-half of questions from the audience on the topics most on their mind. Let’s go....
Dear SaaStr: How Do I Convince My CEO that Marketing is Important?
Dear SaaStr: How do I Convince My CEO that Marketing is Important? A lot of CEOs these days do seem to be late to truly invest in B2B marketing, and most especially, to hiring a true VP of Marketing. In the Age of AI, so many CEOs hack it to $5m, $8m, $20m+ in ARR...
Dear SaaStr: How Do I Know If My New VP of Marketing Is Going To Make It?
Dear SaaStr: How Do I Know If My New VP of Marketing Is Going To Make It? Dear SaaStr: How Do I Know If My New VP of Marketing Is Going To Make It? You’ll know pretty quickly if a new VP of Marketing is going to make it, or not. The best ones deliver real...
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