Dear SaaStr: What Does a CEO’s Typical Week Look Like at $5m-$10m ARR?
Dear SaaStr: What Does a CEO’s Typical Week Look Like at $5m-$10m ARR? Here’s a typical week for a CEO at $5M-$10m ARR. It’s all about balancing recruiting, customer engagement, team alignment, and strategic planning. Let’s break it down day by day: Monday...
Why You Don’t Get Any Credit Anymore for 30% of Your Code Being Written By AI
I was recently at a SaaStr Fund portfolio company event, and a CTO came up to me, clearly excited. He told me proudly how 30% of their code was now written by AI and Cursor. I shrugged. Not because it wasn’t impressive. Not because they weren’t doing good...
Dear SaaStr: What Are the Top “Unspoken Objections” Prospects Have?
Dear SaaStr: What Are the Top “Unspoken Objections” Prospects Have? Objections in a sales process are essentially the reasons or concerns a prospect raises that prevent them from moving forward with a purchase. But .. objections aren’t just the ones that...
The #1 Question to Ask Yourself Before You Take a CRO/VP Sales Role
The #1 Question to Ask Yourself Before You Take a CRO/VP Sales Role Stop overthinking the comp package, the equity split, and the org chart. There’s only one question that matters. TL;DR: Before you say yes to that VP Sales or CRO role, ask yourself one simple...
Beyond Theory: Practical AI Pitfalls to Avoid To Maximize Your Investment with Dialpad’s Chief AI Officer
Jim Palmer, Chief AI Officer, Dialpad came to SaaStr AI Annual + AI Summit to share the top AI mistakes he made building AI Agents at scale for $350m+ ARR Dialpad. Jim is the Chief AI Officer at Dialpad with over a decade of AI experience. He founded TalkIQ, one of...
Dear SaaStr: I’ve Gotten to $1m ARR Selling Myself. What Should I Look For in My First Ever Head of Sales?
Dear SaaStr: I’ve Gotten to $1m ARR Selling Myself. What Should I Look For in My First Ever Head of Sales? You’re in a good spot—above $1M ARR and still founder-led sales. That’s a strong foundation. Now, as you’re automating and refining your sales process,...
20VC + SaaStr is Back!! OpenAI’s Power Move: How Sam Altman Extracted 10% of AMD, Why $5B Pre-Money Rounds Make Sense, and the New Math of Going Public
Sam Altman’s Kingmaker Strategy: Flipping the Chip Deal, The $5B Seed Round Era, and Why Companies at $300M ARR Can’t IPO Bottom Line Up Front: OpenAI has fundamentally restructured the power dynamics in tech infrastructure by securing warrants to purchase...
Your Sales Team Just Has to Be Product Experts. Even if You Have a Hot Hand.
Did a demo today of the enterprise edition of a well known AI product Sales rep: – did not know what MCP is– had never heard of Claude but said "my guys will look into it"– said "your secret to being good at AI was really sick...
Want 600 More Leads? Sponsor SaaStr Annual 2026 + AI Summit By December 15!
So we’ve just finished the Q4 SaaStr AI Digital Day this week and it was a huge success, with incredible sessions including the CRO and CMO of Snowflake! The next one will be late January and for our sponsors, we had record leads, up +20% over past AI Digital...
Dear SaaStr: When a VP Sales is Struggling, What Do They Start to Do That … They Shouldn’t?
Dear SaaStr: When a VP Sales is Struggling, What Do They Start to Do That … They Shouldn’t? Struggling in sales is tough, and you need to give your leadership some time and room to claw back to growth. But here are some signs … they won’t get...
The $1.5 Trillion Software Tailwind: Why Thoma Bravo’s Orlando Bravo Says AI Valuations Are in a Bubble — But Enterprise Software Isn’t
“I’ve been working the hardest I’ve ever worked in 30 years of being in private equity. It’s extremely exciting, but it’s changing very rapidly… I feel that our team, for 30 years since we started, has been training all of our lives...
5 Questions to Ask When Growth Slows
It’s happened far more in the past 24 months than ever before in my years in B2B software. A startup that’s been crushing it for years suddenly hits a wall. Growth rates that used to be 40% quarter-over-quarter drop to 20%, then 15%, then single digits....
Dear SaaStr: What is the Standard Commission Percentage in SaaS?
Dear SaaStr: What is the Standard Commission Percentage in SaaS? In B2B, the standard commission percentage for sales reps typically falls around 10% of the Annual Contract Value (ACV) for deals they close. Sometimes a bit more for orgs rapidly scaling and that are...
Go-To-Market Isn’t Dead. It’s You: A Wake-Up Call for B2B Leaders in the AI Era with Jason Lemkin
In our latest SaaStr AI Workshop Wednesday, Jason Lemkin joined us for “Go-To-Market Isn’t Dead. It’s You: A Wake-Up Call for B2B Leaders in the AI Era” Top 5 Take-Aways: The Same Execs in Many Cases Are Running the Same Playbooks — But...
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