See How Far Your VPs Can Take You. You May Be Surprised.
Our little team at Adobe Sign, we sold a bit too early, so great to see them go on to be: COO of GongSVPS at GongSVPS at SeismicVPS at TalkdeskVPS at CloudinaryGP at Founders Fund, CRO at Brex Great teams do amazing things Keep betting on them — Jason ✨2022...
What Add-Ons You Can — And Can’t — Charge For
I recently was in discussions with senior execs at 3 of the top SaaS companies about their platforms and partners. And all 3 made the same point — their partners can charge for stuff they can’t. Even if it doesn’t totally make sense. For example,...
The Broken State of SaaS Sales Rep Comp
Never met a sales rep that didn't feel underpaid It's just the way — Jason ✨Be Kind✨ Lemkin (@jasonlk) July 19, 2023 Back in the day, premium comp for some software sales execs made simple and easy sense. Traditional software had 90% gross margins,...
Firing the Whole Revenue Team Doesn’t Usually Work
So I remember the first time I saw a CEO fire their entire revenue team. I’d invested in a PLG-first company that was transitioning at millions in revenue to being more sales-led. And the VPs of Sales and Marketing were … well … pretty good. But...
VCs and The Three Types of Struggling Startups
Most VCs won't really give up on an investment if they know the founders are truly giving it 100% But if they sense otherwise, they check out fast — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) June 22, 2025 So there is a lot of triage going on in VC land these...
Should Your Free Edition … Be Even Free-er?
This is important. @Cloudflare is committed to our Free plan. It’s critical to our mission. But, equally importantly, even if no Free customers ever end up paying us, it’s still important to our business. https://t.co/Z6Edy5V3rK — Matthew Prince ????...
Only 11% of Public SaaS Companies Sell Just to SMBs
SMB SaaS has a lot going for it: – Millions of them– Short sales cycles– Easier compete But, it's often hard to get to $100m ARR selling just to SMBs So I took a look at the BVP Nasdaq index Only 11.8% sell just to SMBs pic.twitter.com/Po1I2aMaBK...
Salesforce: “Actually, Things Are Now Slowing Down a Bit — At Least in Some Places”
Workday: “There’s no slowdown at all” Salesforce: “We’re finally seeing slowdown now in our commerce, media, telecom, and SMB segments” It’s still a tale of multiple worlds out there pic.twitter.com/dRPuWG5iZe — Jason ✨2022 SaaStr Annual Sep 13-15 ✨ Lemkin...
It’s Fine to Outsource a Key Integration First. Get It Done.
This post from Gorgias the other day, after it’s $700m valuation Series C, reminded me of a key mistake many founders make. They often wait too long to build a fully native integration: Gorgias is now the leading contact center on Shopify, with over 10,000...
Dear SaaStr: When Should a CEO of a Startup Stop “Doing the Work” and Let Others Do the Work?
Dear SaaStr: When Should a CEO of a Startup Stop “Doing the Work” and Let Others Do the Work? My general learnings: By 20-30 employees, you should have 1-2 good managers in place such that at least 50% of the company can run based only on weekly staff...
Two Strategies for Event Sponsorships: Everywhere. Or Just the Biggest and Best.
Way back in the early days of Adobe Sign / EchoSign, my co-founder was a digital marketing genius — but was opposed to events. They don’t work, he’d say. They take too long to deliver ROI, he’d say. They’re a distraction, he’d...
Dear SaaStr: What’s The Most Challenging Thing for Bootstrapped Founders Once They Raise From VCs?
Dear SaaStr: What is the most challenging thing facing a long-time bootstrapped company immediately after accepting their first investment term sheet? In my experience — not accidentally spending it all, and ending up with way too high of a burn rate. Without...
Whatever You Do, Avoid the Desperation VP Hire
So, we’ve talked a lot over the years on SaaStr on how to avoid a mis-hire for a key VP role: We’ve talked here about the 48 Types of VPs of Sales, and making sure you hire the right type We’ve talked here about how to hire the right VP of Marketing,...
Your New Plan After a Rough Patch: Just Do Better Than The Last 30 Days
Ok for many of you, so much has changed this year. Sometimes, things are even better. Sometimes, worse. Sometimes even, not so much worse as just crazy. No matter what, different. If your bookings dropped, if your churn went way up, then … it did. Things...
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