Dear SaaStr: Is It Worth Working as a Sales Rep?
Dear SaaStr: Is It Worth Working as a Sales Rep? Absolutely. Being a sales rep is the hardest job that almost anyone can get and at least try to do. But boy, you will learn. You will learn: How to hear “No” 100 times in a row. If you can turn 100 “No’s” into 1–2...
How to Make Sure Your AI SDR is Actually Any Good? You Have to First Copy Your Best Human
Most folks deploying AI SDRs and similar tools are doing it all wrong. They think the tool can magically on its own figure out how to sell for you. It can’t. At least not today. None of them can. Here’s what nobody tells you when you’re shopping...
How Personio’s CRO Built an AI-Powered Go-To-Market in Just 6 Months: 5 Lessons and 5 Mistakes
Philip Lacor is the CRO of Personio, a $3B+ HR and payroll platform with 1,500 employees, 15,000 customers, and a 400-person sales team. He shared their AI transformation journey at SaaStr AI London — and the learnings are a masterclass for any revenue leader trying...
CROs at Slow-Growth Companies Often Aren’t Really CROs. They’re Chief Price Raising Officers.
Here’s a pattern I’ve seen play out dozens of times now, and it’s worth talking about honestly. When a B2B company’s growth slows — say, drops from 50% to 20% or even 15% — the CRO role fundamentally changes. Not officially, of course. The...
The Go-To-Market Playbook Isn’t Broken. You’re Just Running the 2021 Version. LIVE with Jason Lemkin
Jason’s Full AMA from SaaStr AI London on What’s Really Changed in B2B Sales in the Age of AI … So Far Top 5 Takeaways The plays all still work — webinars, inbound, outbound, demos. The hottest AI companies are being run by the same B2B sales leaders...
Why The Greatest Sales Teams Just Kill It On Dec 31. When Everyone Else Has Gone Home. (Updated)
So with the end of the year coming up again, it’s time to once update a classic SaaStr post. It may even be our official SaaStr Holiday post, really. On why the best sales teams just close so much on the last day of the year (be it Dec 31 for many of you, Jan...
Dear SaaStr: How Can I Make My Sales Team More Effective?
Dear SaaStr: How do I make my sales team more effective? I get this question constantly. And there’s no shortage of frameworks, sales methodologies, tech stacks, and coaching programs promising to fix your underperforming team. But after investing in hundreds of...
There’s No Excuse For Sales Qualification Meetings in the Age of AI
I had a call with a potential new vendor the other day that reminded me why so many B2B sales orgs are going to get disrupted in the next 1-24 months. They made me sit through a brutal 30-minute qualification meeting. Really longer. And it helped me not one bit. Let...
Yes, Your VP of Sales Also Has to Be a Great Salesperson Themselves
A mistake many founders make is hiring a VP of Sales who has many strengths — but is not great at selling themselves per se. A VP of Sales who is smart, polished, and worked at the right place, in a management-level position. That can talk about quota...
Dear SaaStr: What Are The Top 3 Criteria for Hiring Your First Head of Sales?
We’ve talked a lot on SaaStr about hiring that first VP of Sales. But what if you can’t find the right person, and you’ve spent months looking? What risks should you take when you’ve realized Ms or Mr Perfect just isn’t going to happen...
How Our AI BDR Drove Inbound From 30% to 71% of Revenue from Inbound — By Letting AI Qualify 24/7
Since August, our AI inbound agent has handled 45,188 sessions, qualified 1,025 prospects, booked 91 meetings, and closed $1,010,000 in revenue. In October alone, 71% of our closed-won sponsorship deals in Q4 came from AI-qualified inbound leads. Our historic average?...
Dear SaaStr: Our Sales Team Has a 7% Win Rate. Are We Failing?
Dear SaaStr: Our sales team has a 7% win rate over last 6 months. CEO has put full revenue accountability on the marketing team. How do I keep sales from failing? Not to be too much of a Pollyanna — but a 7% win rate isn’t necessarily all bad. In fact, if you have an...
Stop Looking For Sales Magicians
I see it every single day in my portfolio. CEOs convinced they just need to hire that one rep who will magically turn everything around. And later, that one VP of Sales who will turn things around on their own. The person who can sell ice to Eskimos. The rep who...
If Your CRO, CCO or CPO Doesn’t Meet With Customers Their First Week On The Job … Move On. Apologize, But Let Them Go.
If your new CRO doesn't meet with any customers their first week, Apologize to them. Say it's your fault for making a mishire. And then let them go. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) September 26, 2025 It’s so hard to find a CRO or VP of...
Founder SaaStr
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