In a medium bowl, whisk together light mayonnaise, extra virgin olive oil, white wine vinegar, honey, and Dijon mustard. Season with salt and pepper to taste. Cover and refrigerate for at least 15 minutes.

In a non-stick pan over medium heat, combine brown sugar, water, vanilla extract, and kosher salt. Stir until boiling and thickened slightly. Add the chopped pecans, reduce heat, and stir for 2 minutes. Transfer to parchment paper to cool.

Finely chop the fresh broccoli and set aside in a large mixing bowl.

In the bowl with the chopped broccoli, add cubed sharp cheddar, cooked bacon, dried cranberries, and pumpkin seeds. Mix gently.

Drizzle the chilled dressing over the salad mixture and gently toss everything together.

Transfer the salad to a serving bowl and garnish with cooled candied pecans or refrigerate for up to an hour before serving.