The Reality of Selling Your Company: What No One Tells Founders with Brian Halligan, Co-Founder and Chair of HubSpot
So a little while ago we did a very deep dive with Brian Halligan, co-founder and chair of HubSpot. One of the topics we did a deep dive on was mergers & acquisitions, and it was so good I wanted to just break out that portion of the convo: Net Net: Acquisition...
Are You Fundable Today? Just Ask Your Existing Investors. Just Ask Them.
So Venture Capital is back in force — but not for everyone. 71% of all VCs dollars are going into AI VC dollars are more and more concentrated into winners at growth stage Many traditional B2B VCs are now looking for faster growth than even T3D2 today, in the...
Dear SaaStr: How Should I Specialize My Sales Team?
Dear SaaStr: How Should I Specialize My Sales Team? One thing is clear: most founders and VPs of Sales and CROs look back and wish they’d specialized their sales team earlier. And not have everyone work in a round-robin or similar format on all the leads, just...
The Bar Today for a Series B
Navigating the Funding Gap: Insights from 10,755 US Startups In the world of SaaS startups, securing Series A funding is an achievement worth celebrating. At least for a day :). It’s a sign you’ve hit Initial Traction. But each round usually gets harder. ...
Events Work. Events Are Back. But Are They Worth the Big Expense?
Just got an email from a CEO yesterday that they closed a $450,000 TCV deal from a buyer they met at SaaStr Annual in September Don’t say events don’t work Be where your customers are. Even in the age of AI. — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk)...
Dear SaaStr: I’ve Got 4 Sales Reps. Should My VP of Sales Have Their Own Quota?
Dear SaaStr: I’ve Got 4 Sales Reps. Should My VP of Sales Have Their Own Quota? Maybe. But not much beyond that. If you only have 4 AEs, then it’s reasonable for your Head of Sales to carry a small quota—at least temporarily. At this stage, they’re likely still...
New SaaStr on 20VC! “The VC Playbook: What’s Working in 2025”
We’re back this week on 20VC with Harry and Rory from Scale for another great deep dive on the latest in VC funding and more.  We kick off with a quick deep dive on Vertical SaaS leader for restaurants Owner raising at $1 Billion — a deal SaaStr Fund led...
Our CAC is Way Too High. Should We Cut Marketing To The Bone?
Dear SaaStr:Â We Have a $7m ARR Business But Our CAC is Way Too High. Should We Cut Marketing To The Bone? Look don’t throw money away on sales & marketing. If your sales team can’t close anything, you need to part ways. If you are doing intiatives in...
Dear SaaStr: What Are Some Red Flags an Investor Might Not Be Serious?
Dear SaaStr: What Are Some Red Flags an Investor Might Not Be Serious? First, if you’re not sure they want to invest — they probably don’t want to. And … it’s 100% OK to ask. Just ask. The One Question To Ask At The End of Every VC Pitch: What Are The Odds You Would...
Why Marketing Should Almost Never Report to Sales
Dear SaaStr: When Is It a Good Idea for Marketing to Report to Sales? This is an important but subtle one. On paper, it can seem to make sense for marketing to report to sales in many cases: Your VP of Sales / CRO is often your top leader Marketing’s customer is...
Dear SaaStr: I Don’t See Enough Activity in My SDRs. What Can I Do To Get More From Them?
Dear SaaStr: I Don’t See Enough Activity in My SDRs. What Can I Do To Get More From Them? If your SDRs are struggling to hit targets because of a lack of activities, you need to address both the quantity and quality of their efforts. Here’s what I’d do: 1. ...
5 Interesting Learnings from Atlassian at $5.4 Billion in ARR
So Atlassian is the developer software engine that just keep going: $5.4 Billion in ARR Growing 14% — and importantly, predicting 19% growth for Q4’25 500+ $1m Customers 300,000+ Customers total 5 Interesting Learnings: #1. AI Now At The Center of All...
Dear SaaStr: What’s The Best Ways to Part With A Leader?
Dear SaaStr: What’s The Best Ways to Part With A Leader? First of all, no matter what, remember it’s your fault it didn’t work out. The issue is probably it wasn’t the right fit, or it was the right fit for a while, but no longer is. So treat...
It May Be Easier to Sell a Second Product to New Customers, Not Existing Ones
So this is a seemingly simple post, but it’s a point I find many founders, CROs, CMOs and more get wrong. I got it wrong for a while too, until I started invest in and working with more vertical SaaS companies. And that is something somewhat counterintuitive:...
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