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...
Should You Discount to Save a Renewal? The NRR Trap Says No. You Probably Should Anyway.
The Discount That Would’ve Kept Us So we’re going to churn off Adobe Marketo. The irony: I was one of the first 10 Marketo customers. Ever. I’ve been a customer (with a break) for goodness, the better part of two decades. And a reference account for...
Dear SaaStr: What’s The Best Way to Set Targets for the Sales Team?
Dear SaaStr: What’s The Best Way to Set Targets for the Sales Team? First, I try to model 3 overall plans for the year: C-90, C-60, and C-10, not just for the sales team, but the whole company. The C is for “Confidence”. The odds you think you...
If Nothing Else – Segment Churn. You’ll See Patterns and Learnings You Wouldn’t Otherwise
Churn is not a GAAP metric. It doesn’t have a universal definition. Public companies and startups all seem to define churn differently. And even hide it in part, by doing so. I learned this myself starting out as a B2B CEO. I compared us to the only public...
Dear SaaStr: Is It Normal to Feel Like a Pest When Prospecting for Customers For a Startup?
Dear SaaStr: Is It Normal to Feel Like a Pest When Prospecting for Customers For a Startup? Yes. Most of us will feel like a pest when we start doing outbound. So … get better at it, get over it, and hire folks who know how to do it. Sales is hard. It’s being told No...
9 Signs a Startup Isn’t Going to Make It with SaaStr CEO Jason Lemkin
In a recent Workshop Wednesday, SaaStr Founder and CEO, Jason Lemkin sat down to discuss 9 signs a startup isn’t going to make it.
Sales Used to Be the Engine. For the AI Leaders, It’s Often More the Caboose.
There’s an argument going around right now that sales isn’t as important as it used to be. Still important. Just not as much as it once was. Bear with me here. It’s not an argument I agree with. But I can’t argue with the logic. The point is...
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...
The GTM Stack Anthropic Uses From Its Head of Industries: Surprisingly Familiar Names. Used In New Ways.
You’d assume Anthropic, of all companies, would be running on some self-grown, cutting-edge AI-native sales platform. Maybe a Salesforce killer they built themselves. Maybe Claude baked into the protocol layer of every workflow. They aren’t. At least not...
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 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...
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...
How Owner.com’s CRO Is Closing $2M+ in ARR Per Rep With AI: 5 Things You Can Steal
At SaaStr AI 2026, Kyle Norton, CRO of vertical AI leader for restaurants Owner.com, walked through how his team is generating outcomes that look almost impossible on paper for traditional B2B. Owner sells vertical AI to independent mom-and-pop restaurants (think...
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