How can I develop a stronger typography intuition for a tech startup rebrand?

[Emma2]

I'm a junior graphic designer working on a rebrand for a tech startup, and while I have a good grasp of color and layout, I feel my typography choices are often safe to the point of being generic or, worse, poorly paired, which undermines the modern, innovative feel we're aiming for. I understand basic principles like contrast and hierarchy, but I struggle with selecting and pairing typefaces that have distinct character while remaining highly legible across both dense reports and bold marketing materials. For more experienced designers, how did you develop a more intuitive sense for typography beyond following trends? What resources or practices helped you understand the historical context and emotional weight of different type classifications, and how do you systematically test pairings for both aesthetic harmony and functional clarity in real-world applications?