In a large skillet over medium-high heat, heat 1 Tablespoon of oil until just shimmering. Add pears in a single layer cut side down, season with 1/2 teaspoon salt and 1/4 teaspoon pepper. Cook, turning over halfway through, until golden brown on both cut sides, 4 to 6 minutes total.
Reduce heat to low and add 1 Tablespoon of vinegar. Gently stir until liquid is thickened and coats pears, 1 to 2 minutes. Transfer pears to a plate and let cool. Halve each piece of pear lengthwise.
Wipe the skillet clean and heat over medium-high heat. Toast pumpkin seeds, stirring frequently, until fragrant and just starting to brown and pop, 3 to 5 minutes. Transfer to another plate and let cool.
In the same skillet over medium heat, pour in sugar, shaking the pan so it settles in an even layer. Cook, undisturbed, until sugar melts and is deep golden brown, 4 to 6 minutes. Remove from heat. Using a heat proof spatula, stir in pumpkin seeds and 1/4 teaspoon salt. When pumpkin seeds clump together with sugar, transfer to a plate and let sit until cool enough to handle. Break into small, bite-sized pieces.
In a large bowl, whisk maple syrup and remaining 4 tablespoons oil and 2 tablespoons vinegar; season with salt and pepper. Fold in greens, gently tossing to combine; season again with salt and pepper, if needed. Top with pear slices, candied pumpkin seeds, and cheese.