I don't think this is true. Let $G$ be free on $x,y$, and $H$ the subgroup of index $2$ generated by $x,y^2,y^{-1}xy$.
Consider $h = y^{-1}x^ny \in H$ for some large $n$. The putative word $h_1h_2\cdots h_s$ would at length at most $C$ more than $|h| = n+2$, and would freely reduce to $y^{-1}x^ny$, so it would have to be the word $y^{-1}x^ny$ with at most $C/2$ cancelling generator pairs inserted. Since the word $y^{-1}x^ny$ has no prefixes that lie in $H$, the word $h_1h_2\cdots h_s$ would have at most $C/2$ prefixes in $H$ giving $s \le C/2$, which is not possible if the $|h_i|$ are bounded.