I would want to know two things before answering.
First, do you have good solid footing at the stop sign ... i.e., do you have to stop on a steep crown, or does the climb not start until after you've crossed the other road?
Starting on a steep crown or hill ... I hate that. It's super, super dangerous, especially if the cross road is busy and/or sight lines on the cross road are short. And super especially when it's wet or icy. To the point that I would contact the county engineer and explain the danger to two-wheeled folks (not just bicyclists, but motorcyclists too. And I would have to think it would be pretty dangerous for Amish too - although they aren't in danger of tipping over, which is the greatest danger to two-wheeled vehicles, horseshoes don't exactly have the best traction, horses and harnesses are long so that the driver is well back from the intersection and may not be able to see well, and the buggy and occupants are just dead weight behind ...).
Honestly, what I usually do in that situation is pull slightly past the stop sign before stopping, with my bike turned toward the right as much as possible, to give me better footing and a flatter surface to start from. Then I turn right onto the cross road so I can get some momentum going, then make a U-turn when it's safe. (Or, and you didn't hear me say this, if sight lines are long and there's no cross traffic, I will just slow down enough to see clearly, and then blow the stop sign. To me that's way safer than tipping over, or taking a very long time to get momentum going, and then being immobile in the path of the next vehicle that *does* come along.)
Second, assuming you have a safe start, does the hill flatten out after that initial bump? I don't mean is it the top of the hill, I mean does it become less steep for a while before resuming the climb? The way you specify the initial distance and elevation gain suggests that that's the case.
In that situation, I would actually NOT shift down as much as the others suggest. I would not get into the saddle at all after starting from the stop sign, but stay standing all the way to the top of the bump. (Maybe that's still your low gear, which is cool.) Then when you've climbed that initial bump, you can get back into the saddle, downshift if necessary/available, and spin the rest of the way up.
But if it stays too steep for you to climb in the saddle with your current gearing, past that initial bump, then I would tend to agree with the others ... downshift before you stop, increase your cadence and downshift again as you start the climb, if you still have more gears available continue to downshift whenever your cadence drops, and then just power up as far as you can - you should get farther up as your conditioning improves, until eventually you can get to the top.![]()



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