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 State of Go-to-Market 2026 report is some of the best…
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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 $600K and $1M in bookings. The exact number depends on your deal…
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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 (@jasonlk) February 9, 2024 Here are my 5 simplest ideas to quickly improve sales performance. …
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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 ones, but that’s about it. It is incredibly hard to figure…
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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 now … all you really…
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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 grow, actually the harder this can be, but you need to…
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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 happy customers, then it’s too late. Too late to “take…
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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. The classic test: How…
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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 out at the start. “Great to learn about…
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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. 1. Your Sales Team Needs to Be…
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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…
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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…
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Dear SaaStr: Should a Startup Founder Handle Sales Themself When First Getting Started? The answer is yes – 95% of the time. The “best” sequence for building a repeatable sales engine is roughly: The CEO/founder should close at least the first 10 (or 20 or whatever) customers. That way, she knows. She knows the process,…
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Dear SaaStr: How Long Does It Take the Average B2B Startup to “Exit”? I took a look a little while back at how long it took the average SaaS company that was sold for $1B+ to get that acquisition. The answer? 11.7 years on average, with a median of 10.0 years (maybe the better metric):…
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Dear SaaStr: What Are The Top Things to Know Before Starting a B2B Startup? A lot of founders ask this question hoping to hear something they don’t already know. The honest answer is the opposite. The hard truths about starting a B2B company are mostly things you already suspect but haven’t fully accepted yet. Accept…
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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. Because the role itself is set up to…
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Dear SaaStr: What are some common reasons that CEOs and other top executives are fired? Ironically, it is rarely for missing the plan — at least at start-ups. Rather, execs and CEOs are fired for (x) hiding that they are missing their plan, and (y) blaming others. The reality is VCs and board members know…
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Dear SaaStr: How Long Should I Wait to Follow Up After A Big Customer Pitch? You shouldn’t wait at all. Follow up immediately after the initial pitch meeting. Ideally, within the same day. The best always do. If you can’t do it that quickly, make sure it’s no later than 24 hours. Here’s why: 1. Momentum Matters…
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Dear SaaStr: How Do I Know If It’s The Right Time to Sell My Company? First off, the axiom that companies are bought, not sold, is mostly right. 95 times out of 100, you can’t wake up some morning and just go sell your start-up. Unless there are pre-existing relationships that have expressed a desire…
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Dear SaaStr: When Do You Start to Develop a Brand in SaaS? In my experience, probably as early as $2m worth of happy customers. At least the beginnings of a “mini brand”. At that point, you don’t have a world-famous brand or anything. But you do start to have a “mini-brand”, where folks in your…
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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, leads shop other vendors, etc. That may be…
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Dear SaaStr: I’m Joining a B2B Startup at $3m ARR as VP of Sales. What Should I Do First? Stepping into the VP Sales role at a company with $3M ARR is a pivotal moment. At this stage, the company has likely found some product-market fit, but scaling efficiently and predictably is the next big…
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Dear SaaStr: What sales techniques helped you consistently succeed while others failed? A few that basically always work in sales … but that so many don’t do actually do: Being a product expert. 95% of the sales execs I talk to in software don’t know the product much at all. A huge miss as half…
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Dear SaaStr: I am a startup founder that writes extensive monthly report to investors. We are also doing weekly meetings, are they asking for too much of my time? Yes, that’s too much. Some rough rules: For every 1% of a company an investor owns, they get one meeting / Zoom a year until you…
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Dear SaaStr: What’s considered a large amount of money for an investor? The answer isn’t obvious from the outside. And it’s something founders should know. Is $1m a lot? $100k? $20m? It really varies by VC and by fund. A rough answer is investing more than 1.5%-2% of an individual fund into one deal is a…
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