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 14, 2026 | Blog Posts, Sales
Want to steal a customer from your competitor? 99% of sales reps, 95% of CROs, and 99% of CEOs never ask the one question that would get it done. And it’s so, so simple: “What would it take for you to move over to us? What problem could we completely, 100%...
by Jason Lemkin | Oct 13, 2026 | Blog Posts, Hiring, Q&A, Sales, Sales |
Dear SaaStr: How You Deal With Long Sales Cycles, E.g. 7-8+ Months? "What's the best way to shorten a long saled cycle from 6 months to 4-5 months? Hire a truly great CRO / VP Sales. They know how to do this. They know how to move deals faster. How to talk to...
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 | Sep 26, 2026 | Blog Posts, Hiring, Marketing, Sales |
"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 22, 2026 | Blog Posts, Early, Marketing, Q&A, SaaS Product Pricing, Sales |
Dear SaaStr: Should I Publish My Pricing? If you aren’t sure — then yes. Transparent pricing has many advantages: It makes the sales process simpler. It allows prospects and leads to do more discovery work on their own. And it places your app in pricing context with...
by Jason Lemkin | Sep 21, 2026 | Blog Posts, Growth, Leadership, Sales, Sales |
We’ve talked a ton on SaaStr over the years on how to make sure your CRO / VP of Sales and top hires really work out. That they are the right ones. We can pretty much summarize a lot of it into the following: Your VP of Sales should have lots of experience...
by Jason Lemkin | Sep 20, 2026 | Blog Posts, Career Growth & Advice, Growth, Hiring, Q&A, Sales, Sales |
Dear SaaStr: After closing a few deals myself as a founder, I hired 2 SDRs and closed some more. Should I hire an AE to take over the SDRs and close or a VP of sales? Try to find a VP of Sales now, and try to hire an AE now. You probably will find the solid AE...
by Jason Lemkin | Sep 15, 2026 | Blog Posts, Sales |
Great VP of Sales, first week: – brings 2-4 great sales execs in ASAP. often week 1– identifies top existing talent, does what it takes to keep them– begins to move out underperformers– jumps into all critical deals Mediocre VP of Sales, first...
by Jason Lemkin | Sep 15, 2026 | Blog Posts, Career Growth & Advice, Growth, Q&A, Sales, Sales |
"The #1 mistake founders make when they hire their first VP of Sales? Or even just their first sales rep? They step back from sales. No. You don't get that time back. It's just what you do in sales, changes." pic.twitter.com/wwUzRvrbt0 — Jason...
by Jason Lemkin | Sep 8, 2026 | Blog Posts, Early, Q&A, Sales |
Dear SaaStr: How Long Should You Give a New Sales Rep? The tough truth is from 1.0–1.5 sales cycles. And you’ll often, though not always, know sooner. 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...
by Jason Lemkin | Sep 7, 2026 | Blog Posts, Early, Growth, Q&A, Sales |
Dear SaaStr: I’m Pretty Hands Off on the Sales Team. What Will I Learn Getting More Involved in Sales? The most important thing that you will learn is how businesses truly scale on the revenue side. You may think you know this intuitively, but you don’t:...
by Jason Lemkin | Sep 4, 2026 | Blog Posts, Growth, Hiring, Human Resources, Sales |
Times for many are so different in B2B than they used to be. For those with AI tailwainds, growth is like nothing we’ve ever seen. For those without, it can seem like everyone wants to downgrade or cut. For some, it’s somewhere in the middle. It can seem like...
by Jason Lemkin | Sep 3, 2026 | Blog Posts, Growth, Leadership, Sales |
There’s a set of questions I get asked all the time: Should you pay sales reps on renewals? Should you pay sales reps on upsells a long time down the road? Should you pay sales reps on … ? I am a huge proponent of paying sales professionals well. But for...