We study the quasi-static penetration of a flexible beam in a two-dimensional dense granular medium lying on a horizontal plate. Rather than a buckling-like behavior we observe a transition between a regime of crack-like penetration in which the fiber only shows small fluctuations around a stable straight geometry and a bending regime in which the fiber fully bends and advances through series of loading/unloading steps. We show that the shape reconfiguration of the fiber is controlled by a single non dimensional parameter: L/Lc, the ratio of the length of the flexible beam L to Lc, a bending elasto-granular length scale that depends on the rigidity of the fiber and on the departure from the jamming packing fraction of the granular medium. We show moreover that the dynamics of the bending transition in the course of the penetration experiment is gradual and is accompanied by a symmetry breaking of the granular packing fraction in the vicinity of the fiber. Together with the progressive bending of the fiber, a cavity grows downstream of the fiber and the accumulation of grains upstream of the fiber leads to the development of a jammed cluster of grains. We discuss our experimental results in the framework of a simple model of bending-induced compaction and we show that the rate of the bending transition only depends on the control parameter L/Lc.