5 Ways AI Has Already Changed SaaS Sales Forever with Perplexity’s CBO Dmitry Shevelenko and SaaStr CRO Confidential Host Sam Blond
Perplexity’s CBO Dmitry Shevelenko and host of the SaaStr CRO Confidential series (and former CRO at Brex), Sam Blond at SaaStr Annual share how AI has already fundamentally rewired how SaaS sales works.
In The Age of AI, It Just Won’t Be Enough Just To Be a “Good People Person” in Sales
The #1 objection I hear to AI in sales is that what matters most in sales in B2B and SaaS is being a “good people person”. That does matter. It matter even more in field sales, in-person sales, and true enterprise sales. But is it enough in the age of...
15 Questions VPs of Sales Should Ask CEOs. Before They Take That Job.
Dear SaaStr: I am a candidate for a VP Sales job. What are great questions to ask the CEO? If you’re a candidate for a VP of Sales role, asking the right questions during the interview is critical—not just to impress the CEO, but to ensure the role is the right fit...
30+ Tough Learnings from Losing a Top Customer
On both SaaStr University and Twitter, we had 30+ founders, CEOs and execs share their top, tough learnings from losing one of their top customers. There are some great teachable moments here, and also some deja-vu if you’ve been through it! “I should...
A 10 Point Checklist for Hiring Your First Few Sales Reps
Your first few sales reps have to be … different. A bit of a product savant. A passion for the product and space that almost doesn’t make sense. And someone you can trust with your few, precious leads. "That early sales team … they have to be...
That Super-Successful VP of Sales. Great? Or Just Lucky?
I get sent this resume to review all the time. Director+ of Sales at Slack / Zoom / Mongo / Datadog / Qualtrics Your Brand Name SaaS Company. Took Hot Start-Up from $0 to $50m as VPS from Day 0. Was there “early” through IPO and did amazing things. That all sounds...
“What If I’m Not Sure that My VP Sales is The Right Person?”: An Honest 5 Point Test
Dear SaaStr: What if I’m not sure that my VP Sales is the right person? 🤷♀️If you’re not sure your VP of Sales is the right person, you’re already in a tricky spot. The reality is, at the VP level, you can’t “fix” them if they’re not a fit. And that’s...
4 Unexpected Learnings from Databricks’ Sales Growth Machine From Its VP of Sales
A little ways back Databricks’ VP of Sales Heather Akuiyibo joined SaaStr to share unexpected things that work well at Databricks’ GTM organization … as well as some things that haven’t worked as well. 4 Unexpected Learnings from Databricks’ Sales Growth...
In-Person Sales Generate 3x Higher Conversions Per The CROs of Toast, Splunk, Brex and Slice
In SaaS, it’s easy to assume that virtual selling has completely taken over. After all, Zoom is efficient, email is scalable. Hyrid and work-from-home made it the default paradigm for many in B2B sales. Overall, only 27% of B2B customer meetings happen in person, per...
Dear SaaStr: Should I Let My VP of Sales Go? I’m Not Sure I’ve Made The Right Hire
Dear SaaStr: Should I Let My VP of Sales Go? I’m Not Sure I’ve Made The Right Hire 60 Days In? It depends on what you’re seeing after these 60 days. You don’t need perfection. You do need to see true improvement. Not magic, but some real, tangible...
The Top 10+ Questions to Ask a VP of Sales During an Interview (with Cheatsheet)
One of the classic original SaaStr posts was on the Top 10+ Questions to Ask a VP of Sales Candidate. All the questions still hold today, but I wanted to update them for 2025. It’s a different world today, AI-fueled, often distributed and hybrid, and with...
CRO Confidential: How Windsurf Built A Billion-Dollar AI Company and a Winning Sales Machine with VP of Worldwide Sales, Graham Moreno
Join us on this episode of CRO Confidential as host Sam Blond dives into the remarkable journey of Codium’s VP of Worldwide Sales, Graham Moreno. Discover how Graham led Codium from a 30-employee startup to a unicorn with 150 employees in just one year.
How Much More Should Your Sales Team Do … Than Just Plain Selling?
So in the earlier days especially, you’ll be tempted to lean on the sales team to do more than just … sell. Especially, more after they get an e-signature. Especially because the first 1-2 successful reps you hire will often be a bit of a product expert,...
Dear SaaStr: How Many Sales Reps Do I Need?
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 revenue you need to close in the next twelve months. Because that’s more than now. Second, calculate a...
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