The 30-Day Test: How to Know if Your VP of Sales / CRO Will Succeed
Here’s an uncomfortable truth about B2B companies: the majority of first-time VPs of Sales don’t make it past 12 months. As someone who has both succeeded and failed at making this critical hire, I can tell you that when it works, it’s...
Stripe’s AI CRO on the Fastest-Growing AI Companies: 175% Growth, 48% of Revenue From Outside the Home Market, and Agents About to Read More Stripe Docs Than Human
Stripe processes payments for most of the fastest-growing AI companies in the world, so it sees their actual revenue data. At her SaaStr AI session, Maia Josebachvili, Chief Revenue Officer of AI at Stripe, walked through what Stripe is seeing across its AI customer...
All Platforms Have Their Favorite Partners. Be One Of Them If You Can.
Recently I was catching up with an exec from a B2B company well in excess of $100m ARR. One of the key platforms their app integrates with has started to … slow down their access. Slow down access to new features, to semi-documented APIs. Slow down access to...
The SaaStr AI Guide to Building a Top-Tier Inbound AI Agent: 17,000 Conversations, ~600 Meetings Booked, and 60% More New Business
Our inbound AI agent has had 17,000 conversations with prospects in the last 12 months and booked about 600 meetings for SaaStr AI Annual 2026. And for 2027, it’s running almost 2x of the prior 12 months. Together with the newer self-serve agent we added on top...
Why It May Take You 12-18 Months to Hire a Great VP, Sales — Period. And What to Do About It.
We’ve talked a lot about hiring a VP, Sales.  It’s just such a critical accelerate-or-decelerate decision for a post-Initial Traction SaaS company.   We’ve talked about the 48 Different Types of VP Sales, What a VP Sales Really Does, and a Script to Use...
Dear SaaStr: Why Are Pricing Tiers So Effective?
Dear SaaStr: Why Are Pricing Tiers So Effective? I’m no pricing psychologist or true expert, but a few learnings: Buyers like a >few< choices. Not too many, but 1 or 2. It empowers them. In product marketing and sales, always give a buyer that is interested, but...
Being a System of Record Helps With Retention. But Alone, It Won’t Equal Growth
The other day ServiceTitan shut off Podium’s integration for roughly 1,000 shared customers after a nine-year partnership. LinkedIn and X mostly framed it as a breakup. It’s really a case study in what owning the record can and can’t do for you....
10 Tips To Get Better at Recruiting. We All Need To.
NMBR After $2m in ARR or so, NothingMattersButRecruiting — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) March 9, 2025 Recruiting is tough. I certainly don’t do it well enough. But to be a great CEO, you need to find a way to force yourself to be a great recruiter. Let...
The #1 Clear Sign a VP Will Fail. Be Honest With Yourself When You See It
I’ve seen it again and again across 30+ investments, 10+ unicorns, and hundreds of portfolio company board meetings. There’s one pattern that predicts VP failure better than anything else I’ve seen. Not their resume. Not their pedigree. Not even...
The New Career Path: Joining a 0% Grower. Maybe For Many, It’s Better.
So there’s a new option for seasoned B2B execs now: join something growing … 0%. Ok maybe 0%-10%, let’s call it. This sounds a little wacky described as a career choice. But it’s something some execs have always quietly done, and there are more and...
Focus Your Marketing Efforts on What Your CMO / VP Marketing is Good At
I’ve re-learned something about marketing every year working on the SaaStr AI Annual for 10+ years. And that thing I’ve learned is that you can take two brutally competitive products, that are very similar, give each a booth at SaaStr AI Annual, London or...
The #1 Hack To Making Sure a VP of Sales or Top AE Will Work Out
We’ve talked a ton on SaaStr over the years on how to make sure your CRO / VP of Sales and top hires really work out. That they are the right ones. We can pretty much summarize a lot of it into the following: Your VP of Sales should have lots of experience...
20VC x SaaStr: Pacing the Frontier, Meta Ships Muse And It’s Great, and Miro Sells for $1.35B After a $17.5B Mark
20VC x SaaStr: Pacing the Frontier, Meta Ships Muse, and Miro Sells for $1.35B After a $17.5B Mark Plus: a $1B round at $10B for Instinct, Discovery Loop from $10B to $50B in weeks, and Mistral’s €3B sovereignty round #1. Dario Called for Pacing the Frontier,...
A Full Teardown of How SaaStr AI Actually Runs Inbound, Renewals, and Outbound on the Latest The Agents
We talk a lot on The Agents pod about what our agent stack does. This episode Amelia walked through what it actually, exactly looks like, screen by screen, with the real inputs and the real outputs: the leads, emails and decks that went out this week. Sponsorship...
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