What Every B2B Founder Needs to Know About AI in Go-To-Market Right Now With Jason Lemkin

The Official SaaStr Podcast: SaaS | Founders | Investors · Oct 23, 2025 · 2m

The State of AI + Software: Where It’s Going - Fast

This deep dive is from Jason Lemkin at the LIVE AI Workshop Wednesday. Sign up here for the next one.

I was talking to a founder recently who’s running at $50 million ARR. Classic SaaS guy turned AI guy. And he’s going to scale from $50M to $100M with just five sales reps and a team of AI agents.

In the old days, at $50 million, you’d probably have at least 100 sales reps. Why? Because to get from $50M to $100M, you need $50M in net new bookings. At $500K net per rep (which is pretty good when you factor in scaling, turnover, and ramp time)…