This is the exact same issue as in the previous post (in V9 and later Integrate returns a ConditionalExpression).
Try
ClearAll["Global`*"]
f[x_] = x^2;
s[x_] = Integrate[Sqrt[1 + (f'[t])^2], {t, 0, x}, Assumptions -> x > 0];
FindRoot[s[x] == 5, {x, 2}]
Another way:
ClearAll["Global`*"]
f[x_] = x^2;
s[x_] = Integrate[Sqrt[1 + (f'[t])^2], {t, 0, x}];
FindRoot[Normal[s[x]] == 5, {x, 2}]
And a third way, using _?NumericQ
ClearAll["Global`*"]
f[x_] = x^2;
s[x_?NumericQ] = Integrate[Sqrt[1 + (f'[t])^2], {t, 0, x}];
FindRoot[s[x] == 5, {x, 2}]