How to Become Great at Startup Sales

Honesty and transparency win in the end. Enterprise sales is a trust exercise, and telling an unflattering truth beats manufacturing credibility to keep a deal alive.

The more of an underdog you are, the more you must seek out innovators. Filter for the leaders excited to work with a startup, not the followers who only want credibility.

Your first month at a technical company should go toward understanding the product at a sales engineer's depth, asking engineers even the questions that feel stupid.

Give something of value before you ask for a meeting. 'I wrote a guide, want to see it?' builds trust and opens the door where 'want to hop on a call?' does not.

Define your customer narrowly. Founders go way too broad, but a startup can't sell the world, so write down the ideal size, title, revenue, and tech stack in detail.

Email is getting very noisy. Be intentional about where your buyers already talk about the problem you solve, and take a genuine multi-channel approach to reach them.

It's a give-and-take relationship. Show vulnerability first and the other side opens up. Be a great listener, follow the breadcrumbs, and become a real expert in your space.

Turn weaknesses into superpowers. A stutter became phrases that slow a conversation down; being an outlier became a memorable personality. Confidence is what closes.