by Jason Lemkin | Oct 30, 2026 | Blog Posts, Featured Posts, Growth, Sales |
Annual contracts seem so great. VCs love them, and they do seem to reduce churn. Seem to. In fact, when CROs struggle to hit a plan, they often want to push customers onto annual contracts. That and pricing increases are classic go-to moves. I’ve long been a...
by Jason Lemkin | Oct 29, 2026 | Blog Posts, Growth, Hiring, Human Resources, Q&A |
Dear SaaStr: What Were The First Five Hires You Made After Product-Market Fit? My first 5 hires at Adobe Sign / EchoSign, beyond the core founding+ team, once we had paying customers and first, if early, product-marketing fit: #1: Full-time sales rep at $8k-ish MRR....
by Jason Lemkin | Oct 27, 2026 | Blog Posts, Growth, Q&A, Sales |
Dear SaaStr: How Many Sales Reps Do I Need? More than you probably would think. You can back into how many sales reps you’ll need in SaaS: First, figure out how much sales-driven revenue you need to close in the next twelve months. Because that’s more than now....
by Jason Lemkin | Oct 20, 2026 | Blog Posts, Growth, Q&A |
Dear SaaStr: As a Founder, When Did You Realize You Were Limiting Your Company’s Growth and Success? As we approached $10m ARR, we were doing very well: growing 100%, cash-flow positive, with 100%+ NRR. But I did see that certain of my weaknesses still were...
by Jason Lemkin | Oct 19, 2026 | Blog Posts, Growth, Sales |
So we’ve spent a ton of time over the years on SaaS talking about hiring a great VP of Sales / CRO. Not only because it really matters, but because hiring the wrong one can set you back a year — or longer. So I thought I’d come back to the classic...
by Jason Lemkin | Oct 18, 2026 | Blog Posts, Early, Growth, Hiring, Q&A |
Dear SaaStr: What Role Do Founders Play Once They Hire an Outside CEO? Let me take a slightly different take on the question. Maybe you are really asking – “Am I still on the hook if we hire a ‘real’ CEO to run the company? ‘Cause...
by Jason Lemkin | Oct 14, 2026 | Blog Posts, Growth, Hiring, Sales |
You just can't hire a VP of Sales that hasn't themselves hired a few great reps before At least 2 good sales reps before, that hit or exceeded quotas pic.twitter.com/8f0qiUVPxV — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) February 10, 2024 We’ve talked a...
by Jason Lemkin | Oct 9, 2026 | Blog Posts, Early, Growth |
When a new CRO / VP Sales shows up to the first board meeting and doesn't know: – The top accounts cold– The top deals in flight cold– Their team and leaders cold– The top deals at risk cold There's like 0% chance it will work out...
by Jason Lemkin | Oct 8, 2026 | Blog Posts, Growth, Hiring, Sales, Sales |
"Hiring a seasoned CRO / VP Sales can make sense. But you have to make sure they still want to be … a CRO / VP Sales. That they still want to spend 100% of their time selling. Not being a COO, or President, etc. Not everyone really wants to sell...
by Jason Lemkin | Oct 7, 2026 | Blog Posts, Growth, Sales |
"The #1 thing that undermines confidence in a CRO: Unexpected Bad News. A CRO should have real visibility into the new few months. They may come in a bit above or below plan. But there shouldn't be massive variances. If so, the plan was Hope-ium."...
by Jason Lemkin | Oct 6, 2026 | Blog Posts, Growth, Hiring, Human Resources, Marketing |
"Once you have any customers at all, hire a head of marketing. You really can't hire a VP of Marketing too early. If they just get you another 20%-50% leads, they'll more than pay for yourself. But that doesn't mean hire someone junior that can't...
by Jason Lemkin | Sep 29, 2026 | Blog Posts, Company Culture, Exit Strategy, Growth |
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...
by Jason Lemkin | Sep 28, 2026 | Blog Posts, Growth, Leadership, Sales |
I've never seen a great VP of Sales hide from a miss — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) August 26, 2023 We’ve talked a lot on SaaStr over the years about how to hire a great VP of Sales — and how to course-correct if you’ve made a mis-hire. The two...
by Jason Lemkin | Sep 25, 2026 | Blog Posts, Customer Success, Growth, Hiring, Leadership, Q&A |
Dear SaaStr: How Do We Close Bigger Deals? If you already have a few bigger deals under your belt, but most are smaller … a few higher-level suggestions: #1. Hire a Very Good CRO / VP of Sales that has sold at your “high end” price point. They will be much better at...
by Jason Lemkin | Sep 24, 2026 | Blog Posts, Growth, Marketing, Sales |
Recently I was catching up with an exec from a B2B company well in excess of $100m ARR. One of the key platforms their app integrates with has started to … slow down their access. Slow down access to new features, to semi-documented APIs. Slow down access to...