I Love Our AI Stack. I’m Just Also OK If It’s Completely Different in 2026.
The AI Loyalty Question: Why We’re All Beautiful Betrayers Now And why that’s exactly how it should be in 2025 The confession every founder is thinking but not saying out loud: I love our AI stack. But am I loyal? Will I stick with any of them if something...
11 Signs To Predict If a Venture Investment Will or Won’t Work Out
It's not a flag when a founder picks new VCs for the next one Many reasons for this It's a pretty big flag when none of a founder's last VCs want to invest in the next one Are exceptions, but usually a sign — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin...
A Great VP of Sales Isn’t Great at Everything
We’ve talked a lot on SaaStr over the years about all different types of VPs of Sales. From Stretch VPs to stage-appropriate VPs. A great checklist here to make sure you’re making the right hire. It’s worth also focusing on a related, high-level...
7 Changes You Can Make Today To Grow Faster
Since SaaS compounds, even doing just 5% better now can compound dramatically over time. Everything doesn’t have to be 10x better to move the needle, if it compounds.
But a lot of advice takes time to pan out. What are 5+ changes you can make today, or at least this week, to do better?
10 Marketing Tactics That Always Work for Early-Stage SaaS StartUps
Dear SaaStr: What are the best marketing techniques for an early-stage SaaS startup? My list of things that almost always work in B2B marketing: Try everything — and Double Down on anything that works. If your price point is very low, this sometimes doesn’t work. But...
How Long It Roughly Takes to Close a Deal in SaaS. And Why.
Dear SaaStr: How long does it usually take to close a deal in SaaS? Ok, here’s a really rough set of timelines to how long it takes to close an Opportunity in SaaS: So: A $5k deal, or say $499 a month, can often be closed in a call or two. Certainly the buying...
Hiring Risks vs. Hiring Flags. Make Sure You Get it Right.
My biggest hiring mistake I've made past 5 years that I never made before: I hired folks who didn't really, really, really want the job So far, none have worked out — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) April 16, 2025 During the...
Before You Start as a VP — Please, Please, Please. Do a 60-Day Plan. And Make Sure the CEO Agrees With It.
If you’re feeling relieved you finally got that great VP to join the company, read this from @jasonlk next. (And if you are that VP, definitely read it first.) https://t.co/cVodwksp3N — James Cham (@jamescham) July 23, 2022 I’ve now worked with or invested...
12 of the Most Common Mistakes Scaling Your First Sales Team
Dear SaaStr: What are the most common mistakes founders make hiring their first real sales teams? A few key mistakes I see start-ups making > 50% of the time: Hiring Early Reps (#1 – #3) That You Personally Wouldn’t Buy From. Don’t hire someone with the...
Dear SaaStr: Is it True VCs Don’t Like to Invest Where Founders’ Equity is Fully Vested?
Dear SaaStr: Is it True VCs Don’t Like to Invest Where Founders’ Equity is Fully Vested? Yes, it’s true but … #1. VCs Are Less Rigid Here Than They Used To Be If a deal is hot and you have multiple offers, VCs won’t push as hard here as...
Dear SaaStr: Should I Visit My Customers More?
Dear SaaStr: Should I Visit My Customers More? Yes. Absolutely. You should visit your customers more. I can’t stress this enough—getting in front of your customers is one of the most effective things you can do to drive growth, retention, and expansion. It’s not just...
Dear SaaStr: How Does a First Time Founder Identify 10x Hires?
Dear SaaStr: How does a First Time Founder Identify 10x Hires? How do you hire a great CTO, a great VP of Product, a great VP of Sales … if you’ve never worked with one? It’s hard. If you haven't worked with one before, then, yes, 10x engineers...
Dear SaaStr: How Long Should You Give a New Sales Rep?
Dear SaaStr: How Long Should You Give a New Sales Rep? The tough truth is from 0.5–1.5 sales cycles. Sales is tough. It’s a lot of Nos to get to a Yes. And while sales is pretty similar in SaaS at a given price point / ACV, different products are still different to...
Dear SaaStr: What’s The Toughest Skill to Learn to Scale in B2B?
Dear SaaStr: What’s The Toughest Skill to Learn to Scale in B2B? You need to learn to become a parallel recruiter. To constantly, painfully, boring-ly be recruiting the next level of management and managers — all the time. Doing 30+ interviews a month — minimum....
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