10+ Questions to Ask If You’re Interviewing for a VP of Sales Role
Dear SaaStr: I am a candidate for a VP Sales job. What are great questions to ask the CEO? I’m involved at any given time with 2-3 VP of Sales and CROs searches across SaaStr Fund portfolio companies. One thing is common across all of them: I am shocked how...
The CRO of 2027: The Last Human Standing in GTM?
The Chief Revenue Officer may be the only GTM role that’s truly AI-proof. But one that has to evolve radically over the coming 24 months. We’re watching AI systematically reshape every corner of go-to-market: Customer support? Already largely automated...
8 Top Tips to Building Your Very First Sales Comp Plan
Too many founders make their very first sales comp plan … too confusing. It shouldn’t be. Remember: It’s fine if your first 1-2 sales reps just cover their costs — at first. Ultimately, sales reps just have to bring in 3x-5x what they cost...
The Ultimate SaaStr Sales & GTM Reading List: 30 Essential Articles Every Revenue Leader Must Read
The go-to-market landscape has fundamentally shifted in the last 12-18 months. Older playbooks don’t seem to be working as well. And at the same time, the native AI leaders are growing at a pace we’ve simply never seen before. We’ve assembled 30 of the most...
Dear SaaStr: How Do You Handle It When a Prospect Puts a Deal “On Hold”?
Dear SaaStr: How Do You Handle It When a Prospect Puts a Deal “On Hold”? When a deal goes “temporarily on hold” in your CRM, it’s critical to treat it as a live opportunity, not a lost one. The key is to stay engaged without being overly pushy....
Why Most SDRs Will Be AI SDRs In 2026+. It’s Not Just About Productivity.
I’ve been in SaaS since 2005 (!). I’ve worked with a number of great SDRs … and a bunch that were there and gone in just a flash. I’ve sat through thousands of sales calls. And now that we’ve rolled out 4+ AI SDRs and BDRs at SaaStr itself,...
What A New VP of Sales Needs To Be Doing Their First 2 Weeks
Dear SaaStr: What Should The First 2 Weeks Look Like For a New VP of Sales? The first two weeks for a successful VP of Sales in a B2B company should be laser-focused on understanding the business, the team, and the customers. Here’s what they should prioritize. If...
How to Build a Good Basic Sales Plan for Your First SDRs
Dear SaaStr: What’s a Good Comp Plan for Our First SDRs? A good SDR compensation structure should be simple, motivating, and aligned with your business goals. Here’s how I’d structure it: 1. Base Salary + Variable Compensation: 60/40 Or So SDRs typically have a...
10 Things Startups Get Wrong Selling to Developers and Engineers (from the CRO Who Scaled Databricks from <$1M to $3 Billions)
Lessons from Ron Gabrisco, CRO at Databricks, who joined when the company had less than $1M ARR and helped scale it to become one of the largest pre-IPO companies in the world. Selling to developers and engineers isn’t like selling to any other buyer....
We Thought These Leads Were Dead. Our AI Proved Us Wrong (And Booked 4 Meetings in 48 Hours)
When AI Resurrects “Dead” Leads: A SaaStr Case Study on What Sales Teams Miss, But AI Can Catch Our sales AI reactivated 4 leads in past 48 hours that our human sales team said were dead / not-interested All took a meeting asap Something to reflect on...
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...
Sometimes All Your Bigger Customers Want is Just To Be Heard
Just remember, i know they stress you out and drive you a bit nuts But the customers that complain the most are often the ones that care the most. At least, it shows they aren't leaving. Yet. — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) December 9,...
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...
Outbound Always Works. If You Do It Right. And You Put In The Time.
"Crummy outbound may not work that well these days. But great outbound still works like magic." pic.twitter.com/DwjcgRLOVA — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) January 31, 2025 These days, it can really feel like the Old Bag of Sales...
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