Zig-zag your way across GTM roles | Chapman Swaine, Ashby

Pre-Sales Pathways · Oct 19, 2026 · 42m · transcript

Lots of SEs are considering a move into sales. Chapman Swaine did the reverse, twice.

At Slack, he went from enterprise sales to building out the value consulting team.

Then he joined Ashby as its second sales hire, before building out the SE function from scratch.

Today, he works on special projects across Ashby’s GTM org, reporting directly into the VP of Sales.

Every move in his zig-zag career has been intentional, rooted in his values and what he wanted from his career.

In our conversation, we get into:

Why time spent selling builds skills you can’t fake

How to handle your ego when you…