Matt started on a Monday and was on the phone by Tuesday. He didn't fully understand the product yet. That didn't stop him. He wanted a fast start and he wanted the founder to notice.

Nights and weekends, he learned everything he could about the industry. He listened to old calls. He booked meeting after meeting. By week three his calendar was back to back.

Buyers pushed back, the way they always do. Matt made up his own answers to their objections. Some were probably fine. Some probably weren't. He never checked. The founder was busy, and Matt didn't want to bother him. He figured being able to sell what he had, without asking for help, was exactly what a founder wants in a first seller.

So everything the market was telling him stayed with Matt. Which objections kept coming up. Which features buyers asked about. Where deals stalled. None of it reached the founder.

Six weeks in, everyone was impressed. Lots of meetings. Lots of effort. No closed deals.

Then the questions started. Friendly ones. "How are we progressing? Any of these going to close?" Nobody was worried yet.

Month four, it was a performance problem. That's when Matt finally told the founder what the market had been saying for three months.

Matt worked plenty hard. He made two communication mistakes, and they were the same mistake running in two directions.

First: he never asked what results the founder expected, and by when. Your founder already has a number for day 60. If you don't ask, you'll hear it in month four, framed as a performance conversation. So ask in week one, plainly: "What does success look like at day 30, day 60, and day 90? What pipeline, what opportunities, what closed revenue?" Write it down. If the number is unrealistic for your sales cycle, say so now. In month four, the same point sounds like an excuse.

Second: he never agreed on how what the market was saying would get back to the founder. Your founder needs that information more than any closed deal in your first 90 days. The objections you're hearing are product feedback. Your improvised answers are a messaging decision the founder never got to make. Set it up in week one: a standing weekly time to bring back what buyers are saying, which objections you can't answer, and where deals are getting stuck. Across the 300+ founder conversations behind my work, the founding AEs who make it almost always had a founder giving them 5 to 8 hours a week in the first 90 days. This is what that time is for.

Going it alone feels impressive. Mostly it means your founder learns about the market three months late, and learns about you at the same time.

Week one has another conversation worth having too: how the founder actually closed their last three deals. I walk through all of it here.

But start with these two. A founding AE rarely loses the seat for working too little. They lose it for working without the founder knowing what they're learning.

If you're open to a move: every founding AE role I'm working on is listed here, with comp listed.