Preheat your oven to 400°F.
In a small bowl, mix together the softened butter, thyme, rosemary, garlic, and a pinch of salt and pepper. Set aside.
Use half a Tablespoon of the steak seasoning for each of the steaks, and season all sides of the steaks while gently pressing down to adhere it to the meat. Wrap a slice of bacon around the sides of each steak, then secure it where the ends meet with a toothpick.
Heat a large cast iron or ovenproof skillet over medium-high heat. Once hot, add the olive oil and swirl to coat the bottom of the pan, then place the steaks in the skillet.
Sear the first side for about 1-2 minutes until it develops a golden-brown crust.
Flip the steaks over and sear the second side for another 1-2 minutes.
Remove one steak to a clean plate. Use tongs to carefully hold the other steak on its side to sear the bacon-wrapped edges. Rotate the steak to ensure all bacon edges are seared, about 30 seconds to 1 minute per side. Repeat with the remaining steak.
Return the steak to the skillet, and insert an oven safe meat thermometer into the thickest part of one steak. Transfer the skillet to the preheated oven.
Bake for approximately 8-12 minutes or until it reaches an internal temperature of 130°F for medium-rare doneness, keeping in mind that the internal temperature will raise roughly 5°F due to carryover cooking. Keep in mind that it is recommended to cook beef to 145°F, but individual preferences vary. For the internal temperatures for different levels of doneness, see notes.*
Once the desired doneness has been reached remove the steaks from the oven. Transfer the steak to a cutting board, top each steak with a dollop of the prepared herb garlic butter, and tent lightly with aluminum foil. Let them rest for 5 minutes to allow the juices to redistribute throughout the steak.
***IMPORTANT: Remember to carefully remove the toothpicks before serving.***