Honestly, the moment I realised I needed to stop doing founder-led sales was when I could feel myself repeating the same conversations over and over, but still not having anything solid to hand over to someone else. If you haven't already, start recording your calls and building a library of email templates. That structure is everything.
Without it, you're just passing on your gut instinct, which doesn't scale. As a founder, you'll always care more about the product and notice the tiny details that make a difference in a pitch. That passion is golden, but it's also a trap if you're trying to delegate.
The biggest time-saver for me was figuring out where my own skill gaps were. Either hire someone who can take you upmarket - enterprise stuff, qualifying properly, navigating complex teams, creating the kind of content that sells without you being in the room. Or hire someone to go downwards - finding prospects, running those ten-minute qualification calls that burn your day but are essential.
Both motions have chunks that are repetitive and not uniquely you. Those are the bits to hand off first. You'll thank yourself later.