- To caramelize fennel, heat a cast iron skillet over medium heat. Add enough canola oil to cover the bottom of the pan by ¼ inch. Sear fennel in batches on both sides until golden brown. Remove to a paper-lined sheet pan and season with salt and pepper. Repeat with remaining wedges.
- To make aioli, add all aioli ingredients except oil to blender. Blend on high to thoroughly incorporate. With blender running, add oil until consistency is slightly thicker than heavy cream but less thick than mayonnaise.
- To assemble salad, cut avocados into wedges, cut tomatoes in half, and season both with salt and pepper. Place about 3 tablespoons of aioli in the bottom of each salad bowl. Add warm fennel then avocado, tomatoes, pine nuts, and garnish with fennel fronds. Drizzle olive oil and a squeeze of fresh lemon to finish.