The Pentester Blueprint
https://www.slideshare.net/pwylie1/the-pentester-blueprint-a-guide-to-becoming-a-pentester-3cs-2019
https://www.bugcrowd.com/resources/webinars/so-you-want-to-be-a-pentester/ (same talk under different title)

SANS Institute: sans.org
eLearn Security: eLearnSecurity.com
Virtual Hacking Labs: virtualhackinglabs.com
Pentester Academy: pentesteracademy.com
Pentester Lab: pentesterlab.com
Practical Pentest Labs: practicalpentestlabs.com

Bugcrowd University: bugcrowd.com/university/
SANS Pentesting Blog: pen-testing.sans.org/blog/
HackingTutorials.org
Web Security Academy: https://portswigger.net/web-security
Cybrary.it
owasp.org
Hack The Box: hackthebox.eu
Over The Wire CTF: overthewire.org/wargames/

Books
Penetration Testing: A Hands-On Introduction to Hacking

The Hackers Playbook 2 & 3

The Web Application Hacker’s Handbook: Discovering and Exploiting Security Flaws 2nd Edition

RTFM: Red Team Field Manual