SaaStr Comes to JAPAN November 20 for the All Star SaaS Conference!
The 9th All Star SaaS Conference is November 20 in Tokyo and we’ve been meaning to go for a while. The stars aligned this year and I’ll be there speaking, including an AMA, along with several other top SaaStr speakers: Rob Bernshteyn, CEO of Coupa, and...
Can a Sales Team Ever Catch Up For a Slow Year in Q4?
So if you’ve been around startups for a while, and especially sat on any boards, you’ll see a VP of Sales answer a slow Q1 and even Q2 with this: “We’ll make up for it in Q4.” And many variations thereof. In fact, in so many sales plans,...
5 Interesting Learnings from Samsara at $1.26 Billion in ARR
So whose doing well in SaaS today — with almost no “macro” impacts? Folks that sell to the end economy in the U.S. Like Samsara. Powered by the overall strength of the U.S. economy, by shipping, by trucking, by industrial applications and more...
No, It’s Not Any Harder to Get Funded Today. Not Really.
So many on social media are lamenting how much harder it is to raise venture funding today than it used to be. And the data nominally suports it. Statistically, raising a Series A is 2x as hard or harder than it was in 2021. But that doesn’t really mean...
Dear SaaStr: What 3 Mistakes Did You Make in Your SaaS That You Wish You Could Go Back in Time and Fix, to Accelerate Growth?
Dear SaaStr: What 3 Mistakes Did You Make in Your SaaS That You Wish You Could Go Back in Time and Fix, to Accelerate Growth? Every year that I think about it, the top 3 sort of change. But my Top 3 mistakes I made as a SaaS CEO: Not constantly hiring, especially for...
Toast: We Made Our Sales Reps Close More, And Shrunk Their Territories. It Worked.
So Toast is one of the most iconic B2B leaders out there. We’ve all used Toast 10s or 100s of times by now. But while the brand and market penetration is strong, the business model is challenging. It still loses money on the hardware, and the payments side is...
Dear SaaStr: Who Should I Fire, Someone Who Underperforms, or Someone Who Has Questionable Ethics?
Dear SaaStr: Who Should I Fire, Someone Who Underperforms, or Has Questionable Ethics? I would fire both. An underperforming rep that gets a pass just lowers the bar for everyone, unfortunately. No matter how nice they are. If it’s OK for Bob to always hit 30% of...
10 Hacks to Have Happier Investors
At least up until $10m-$20m ARR or so, If you haven't gotten your investor updates out by the 10th of the month, VCs assume it's not good If you haven't gotten your investor updates out by the 15th of the month, VCs assume there's trouble — Jason...
Dear SaaStr: How Many More Junior Marketers Should you Hire Before Hiring a VP of Marketing?
Dear SaaStr: How Many More Junior Marketers Should you Hire Before Hiring a VP of Marketing? Unlike many positions, I say 0 if possible. In fact, one of the 10 most unforced errors I see founders make is hire someone too junior to get marketing going. If you are,...
10 Simple Ideas to Help Manage the Burn
So, for many of us in SaaS, these are still some of the best of times. The Cloud is bigger than ever, CIOs are buying more than ever, and SaaS is still on a roll. But public stock prices are way down, and venture capital is much tighter than it was outside of AI...
Dear SaaStr: What Was the Moment You Knew You Had to Break Up With Your Co-founder?
Dear SaaStr: What Was the Moment You Knew You Had to Break Up With Your Co-founder? It’s happened to me twice, that “moment”. It was the same thing both times: When they just didn’t show up to a critical meeting. Founder conflict is unfortunately pretty common. I was...
Do Angel Investors and Seed VCs Ask for Detailed Budgets Before Investing?
Dear SaaStr: Do angel investors or seed venture capitalists normally ask for detailed budgets including cash flow analysis before investing, even though most of the numbers will be pure speculation? Many do. Why? Even if you are very early stage, It’s really one of...
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....
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