Consider first the iterated integral $I=m!\int_0^x\int_0^{x_1} ... \int_0^{x_{m-1}} \prod_{i=1}^m dx_i f(x_i)$.
By permuting the dummy indices, we can reorder $x_1$ to $x_m$ to find new expressions for $I$. By adding all of these expressions together and dividing by $m!$, we recover:
$$m!\int_0^x\int_0^{x_1} ... \int_0^{x_{m-1}}\prod_{i=1}^m dx_i f(x_i) = \left(\int_0^x dy f(y)\right)^m.$$
Now consider the sum: $$S = m! \sum_{n_1=0}^n \sum_{n_2=0}^{n_1} ... \sum_{n_m=0}^{n_{m-1}} \prod_{i=1}^m a_{n_i}$$
Using the same tactic used on the integrals for $S$ for the case of $m=2$, I find that $$2!\sum_{n_1=0}^n \sum_{n_2=0}^{n_1} a_{n_1} a_{n_2} = \left(\sum_{j=0}^n a_j\right)^2 + \left(\sum_{j=0}^n a_j^2\right)$$ so it is clear that there are necessarily extra terms relative to the integral case.
How can I simplify the form of $S$? Since the choice of $a_n = 1$ simplifies nicely for general $m$ because of the hockey-stick identity, perhaps there is a straightforward combinatorical path.