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Latest posts

Last updated about 21 hours ago

Beware the “Mediocre Recycled.” The Zombie Executives of B2B + AI.

about 23 hours ago

So I wrote a version of this post a while back, and...

A Checklist: 10 Signs You Shouldn’t Hire a Sales Rep

over 2 years ago

Never hire anyone in sales that doesn't care about money You'll see...

90%-95% of Salespeople Won’t Make It At Your Startup. A 6 Part Test to Help You Get It Right.

over 3 years ago

Most salespeople will succeed somewhere … but fail at >your< specific startup...

Pylon’s Founders at SaaStr AI Day: A 1,000-Person Support Team Deflected 50% of Its Tickets. Headcount Didn’t Change.

2 days ago

Marty Kausas and Advith Chelikani on why deflection rate is the wrong...

How Mailchimp Went From $1B+ ARR to … Shrinking Inside Intuit. A Death Spiral in the Age of AI?

3 days ago

A product that won by doing one thing perfectly spent seven years...

When You Hire Your First Sales Rep — Just Make Sure You Hire Two

almost 3 years ago

"When you go to hire your first few sales reps — they...

Atlassian Just Deleted Loom’s Free Creator Seats. They Were Also Loom’s Distribution.

4 days ago

It wasn’t even 30 days after I left Adobe after their acquisition...

Dear SaaStr: What Is A Good Demo Conversion Rate for a SaaS Startup?

4 days ago

Dear SaaStr: What Is A Good Demo Conversion Rate for a SaaS...

The Simple Math Behind a 3x Venture Fund: Why Your Best Investment Needs to Return the Whole Thing

5 days ago

One of the questions I get asked most often by new VCs...

Backstory Retiered Its Entire Customer Base in 3 Days. The Same Exercise Used to Take Five Teams a Quarter.

5 days ago

Haya Kamola on running an account tiering analysis with connectors, custom signals...

5 Interesting Learnings from Shopify at $14B in Revenue: 34% Growth, 18% Free Cash Flow Margins, and AI Orders Up 3x

6 days ago

Shopify reported Q2 2026 this week and the stock jumped roughly 18%...