SaaStr Annual 2025 is May 13-15 in SF Bay!!
So you may have noticed there are now a ton of events in September. This year SaaStr Annual was the week before both Dreamforce and HubSpot’s Inbound, as well as Oracle’s big event. As well as many other super cool events, from The All In Conference to Acquired...
The 3 Types of Hires You Just Can’t Make Today: The Jaded, The Broken, and The Done
There are 3 types of hires you may be tempted to make now, but you just can’t: The Jaded, The Broken, and The Done They’ve always existed, it’s just there are so many more folks with great LinkedIns and experiences in these categories in SaaS....
5 Interesting Learnings From HubSpot at $2.5 Billion in ARR
So we’ve covered HubSpot a lot on 5 Interesting Learnings, but there’s a good reason — it’s the SaaS leader the most like most of us. Most of us use HubSpot. Most of us are building products in some category HubSpot plays in, from sales to...
Dear SaaStr: We’ve Gotten a Good But Not Great Acquisition Offer. Should I Take It?
Dear SaaStr: We’ve Gotten a Good But Not Great Acquisition Offer. Should I Take It? Should you sell your startup if you get a good M&A offer? For years, while I pretended to be neutral on this question, I’d still quietly root for founders not to sell...
HubSpot and Shopify Are Both Going More Enterprise. But Also — More SMB.
So two of the great leaders in SMB SaaS, Shopify for e-commerce, and HubSpot for sales, marketing and more, are going more upmarket: HubSpot 100+ seat deals are up 55% Shopify now gets 31% of its revenue from “Plus” or its bigger brands and more enterprise...
Dear SaaStr: When Will VCs Push You To Bring On an Outside / Professional CEO?
Dear SaaStr: When Will VCs Push You To Bring On an Outside / Professional CEO? I think 99% of successful VCs, especially “traditional”, experience Silicon Valley-type VCs have now seen you want to back the founder-CEO forever if you can. You sometimes...
There Probably Is No Downturn in SaaS. It’s Time To Stop Waiting For It To End.
How badly do you >really< want it? This will be the question for many founders in 2025 — Jason ✨👾SaaStr.AI Sept 10-12✨ Lemkin (@jasonlk) September 16, 2024 So the past 24 months have been such an odd time in SaaS and Cloud. Some parts of it are on...
Dear SaaStr: Is a Strong Social Media Presence Important as a CEO?
Dear SaaStr: Is a Strong Social Media Presence Important as a CEO? Onestream is the latest SaaS IPO. Bootstrapped to $100m ARR. The CEO has never posted on LinkedIn. Not once. And he’s a 2x successful founder. Selling to CFOs and finance. On the other hand,...
5 Of The Top SaaStr Podcasts of the Year: Yext/Roam CEO, Brex CRO, Owner’s CRO, AI Pricing, and The Top 10 Mistakes Founders Are Making
Trevor Lee, founder CEO at Myko, put together his list of his favorite SaaStr podcasts of the year, and they really are some of the best ones. I’m all in on these Top 5. Listen / watch them to really learn. If you want to catch up, these are 5 great ones: #1. ...
The Best Stuff to Sponsor ASAP, Right Now, at 2025 SaaStr Annual. It’s May 13-15 2025!!
So I know we’ve just finished the 2024 SaaStr Annual, but we’ve learned a lot from it, even in Year 10. One is that some of the very, very best stuff to sponsor goes fast and often is N=1 in terms of availability. And 2025 Annual is earlier this year...
What’s a Mature SaaS Company at $240m ARR Really Worth? Maybe 3.6x ARR
So TechCrunch had a good story on a 19-year journey of Sharefile to an $875,000,000 exit. It was founded way back in 2005, back when my last SaaS startup was, so I have a dim memory of it. Fast forward to today, they’ve sold for a stunning $875 million. But...
Just Being Pretty Good at Venture Capital Isn’t Good Enough
So Carta has some of its latest data on VC performance and it’s pretty interesting: There’s a lot going on this chart but let me break it down from a founder perspective: The median 2017 fund is 7 years into a 10-14 lifetime — and is sitting at 1.8x...
Dear SaaStr: When Is the Best Time for a Co-Founder to Leave a Startup?
Dear SaaStr: When Is the Best Time for a Co-Founder to Leave a Startup? The best time to quit is the earlier of (x) 6 months from the time you’ve decided to move on or (y) at any time when the other founders ask you to. If you’ve truly decided to leave, then it’s...
5 Interesting Learnings from Rubrik at $920,000,000 in ARR
So there have only been 3 SaaS IPOs since 2021. Just 3. But all 3 are pretty good ones: Klaviyo, blowing past $1B in ARR; OneStream, growing 37% at $500m ARR; and Rubrik, growing a stunning 35% at $920,000,000 in ARR. (Note: Rubrik’s ARR and growth numbers...
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