Abstract: A drill bit includes a shank, an intermediate portion with a helical flute, and a multi-stepped tip portion extending along the axis. The tip portion includes a cutting tip with a pair of primary cutting edges extending radially outward from the axis, a plurality of steps each having an elongated portion and a tapered portion tapered outward from the elongated portion relative to the axis. The elongated portions progressively increase in diameter from the cutting tip to the intermediate portion. The elongated portion of each step has an axial relief tapered inward toward the axis. A frontmost elongated portion has a first axial relief at a first angle relative to the central axis and a rearmost elongated portion has a second axial relief at a second angle greater than the first angle. The drill bit may be used as a pilot bit together with a holesaw in a system.