I spent the first chunk of my career doing sales (2nd half spent in software engineering). Theres a lot of good books out there but you're going to find a lot of the direct advice to be non-applicable (as I'm sure you can pick up from the comments). Most of the Literature out there is directed at professional sales people, who for the most part are non-technical, have the backing of a marketing org, and are also different than a founder. Anyway, heres a reading list. Most of the trainings I've been a part of were custom built to the org or market, and frankly I learned more from Rules of the Game by Neil Strauss. I did enjoy "the Wedge" training by Randy Schwantz... that one you should do the video not the book. It also sounds like you could use some marketing stuff so I'll throw some of that in there too.

In no particular order, and please keep in mind this is off the top of my head:

* Influence (the classic)

* YC videos (e.g. https://youtu.be/0fKYVl12VTA?si=I9uylXSRyOf1nXRv, https://youtu.be/DH7REvnQ1y4?si=Ke858PmaaBr5ar-e, https://youtu.be/hyYCn_kAngI?si=sO_co6kbDaNn3cql, etc)

* Thinking Fast and Slow

* Purple Cow

* Clayton Christensen stuff

* Spin Selling

* Challenger Sale

* Guerrilla marketing (for the mental muscle)

* Jeffrey Gitomer (basic but useful)

* Lean Startup (for positioning)

* Charisma Myth

* Minimalist Entrepreneur (bits and pieces)

* The presentation secrets of steve jobs (just a good book on presentations, framed around Steve Jobs to sell more)

For what its worth this question comes up fairly often. It seems like technical people would like a "technical people" guide on how to do Sales and marketing. Does that sound useful to anyone?