We replaced our sales team with 20 AI agents—here's what happened next

At the end of each meeting, learn to ask for what's the next step. The best salespeople never leave a meeting without a next step.

"Reps" refers to sales representatives - the first salespeople you hire for your startup.

Those first couple reps have to be people you would buy your own product from. That's it.

A sales rep's got to bring in four to five times what they take home. The more enterprise you are, the bigger the multiple has to be.

Story points are development team capacity units used in agile project management; "pie chart" refers to overall development resources allocation.

Every quarter, give your head of sales a certain budget, whether it's story points or 10% of the pie chart. When you do this, things will radically change.

This stress between product and sales is a good thing. It's a sign of a well-run B2B company when there is stress between product and sales.

The great VP of Product are deeply involved in sales. When you have that magical VP of Product that truly owns the roadmap, they become like the mini CEO in these meetings.

I'd much rather have two reps, each closing a million than 20 reps struggling to close 100k each. Culturally, it's terrible.

Who's your VP of Free? If you have this massive free base, who's your VP of Free? I know almost no one that has a VP of Free.

Be kind. When I reflect on my career, mistakes, I don't think I'm mean, but it's not taking the time to be kind at times and not taking time to be kind when things don't work out.

Make this the year of the customer. Product teams have to step up. Be the voice of the customer. Be the VP of free, be the whatever. Be the champion.

Here's the mistake that 99% of founders and sales reps make. We're not really selling in B2B, we're solving problems.

You need two sales reps hitting quota closing deals before you're ready to hire a manager for them.

"Colombo questions" refers to asking seemingly simple, open-ended questions that reveal deeper insights, like the detective character Colombo who solved cases through deceptively basic inquiries.

When I interview, I always do Colombo questions. What would you do your first 14 days as VP of product here? And they don't want to visit customers. Don't hire them.