Reroll. The healing surge for success applies to things like combat/utility dailies that don't have mechanics that interface with the skill system and have narrowed fictional positioning requirements. If the fictional positioning can be mapped, then you can spend a surge, lose the daily, accrue a success.
With these kind of skill dailies, they're basically open-ended, broad buffs to your skills (which basically makes them fictional positioning neutral, therefore always applicable), typically for the duration of the scene and you don't spend a surge; you just get 2 rolls for all Athletics and Endurance checks for the duration of the scene. If you deploy now, you get a 2nd roll for Athletics and if you used Endurance later (or Athletics again - which would automatically be at the Hard DC due to the 2nd use), you would get to roll twice for your result there as well.