I will present a way to count the number of permutations in $S_n$ composed of exactly $k\le n$ cycles, that will naturally give expressions of the form $\sum_{i_1\cdots i_k=1}^{n} (i_1-1)\cdots(i_k-1)$, which as mentioned in the question equals ${n\brack k}$.
Specific example: ${4\brack2}$
To this end, I'll start from a specific example, and only afterward discuss the general approach. Consider then the permutations in $S_4$ composed of two cycles. There are two cycle types compatible with having two cycles: $(22)$ and $(31)$. We will list the possible permutations $\pi\in S_4$ as follows:
Start asking where $1$ is sent by $\pi$, that is, what is $\pi(1)$. If $\pi(1)=1$, then we are dealing with a (31) cycle. We then take the lowest "unused" integer (so in this case $2$) and ask what is $\pi(2)$. Now, because we want two cycles overall, $2$ must belong to a 3-cycle, meaning $2\neq\pi(2)\neq\pi^2(2)$ and $\pi^3(2)=2$. Counting the corresponding number of permutations is easy: $1$ and $2$ are fixed, and the remaining number of 3-cycles are $2\times1=2$. In other words, we just counted the number of permutations of the form
$$(s)(s\,{\bullet}\,{\bullet}).$$
We'll use this notation again in the following: each $s$ means "fill this place with the smallest available integer", and each $\bullet$ means "any available integer can be put here". So to be more explicit, the two $S_4$ permutations compatible with $(s)(s\,{\bullet}\,{\bullet})$ are
$(1)(234)$ and $(1)(243)$.
If $\pi(1)\neq1$ but $\pi^2(1)=1$, then we have a $(22)$ cycle structure. We will use the same approach as above to count these: we consider permutations of the form
$$(s\,{\bullet})(s\,{\bullet}),$$
which includes $3\times1$ permutations, and more specifically, the permutations $(12)(34), (13)(24)$, and $(14)(23)$.
The last remaining possibility is that $1$ fits in a 3-cycle. This means cycles of the form
$$(s\,{\bullet}\,{\bullet})(s).$$
There are $3\times2$ of these, which are explicitly
$$(123)(4),(124)(3),(132)(4),(134)(2),(142)(3),(143)(2).$$
Let me stress that, while these permutations have the same cycle structure as in the point 1 above, there is no overlap between the permutations in $(s\,{\bullet}\,{\bullet})(s)$ and those in $(s)(s\,{\bullet}\,{\bullet})$, meaning we can simply sum the individual counts to get the total number of permutations of cycle type $(31)$.
So, overall, we found that the number of $S_4$ permutations with two cycles equals $2\cdot1+3\cdot1+3\cdot2$, which is exactly the expression we were looking for.
General case
More generally, our approach to count $S_n$ permutations with $k$ cycles is to count such permutations by writing all possible expressions with $s$ and $\bullet$ like above containing $k$ cycles.
This, however, leaves the problem of having to "select" the appropriate cycle structure when writing down the expressions. Fortunately, this is not really a problem: we can observe that the parentheses in the above expressions are completely redundant: we could have equivalently wrote $ss{\bullet}{\bullet}$ and $s{\bullet}s{\bullet}$ with no ambiguity as what is the corresponding cycle structure. The strings are understood as prescribing that a new cycle is started every time we get an "$s$" symbol.
We can thus conclude that the possible $S_n$ permutations with $k$ cycles are all and only those coming from strings of length $n$ containing "$s$" and "$\bullet$", with exactly $k$ copies of "$s$", with the additional rule that the first symbol is always an "$s$".
As an additional example, that means to count ${5\brack 2}$ we consider strings of the form
$$sss\,{\bullet}\,{\bullet},
\qquad ss\,{\bullet}\,s\,{\bullet},
\qquad ss\,{\bullet}\,{\bullet}\,s,
\qquad s\,{\bullet}\,ss\,{\bullet},
\qquad s\,{\bullet}\,s\,{\bullet}\,s,
\qquad s\,{\bullet}\,{\bullet}\,ss.
$$
It is easy to count the number of permutations in each of this strings: we just multiply the positions corresponding to each of the $\bullet$ in the string, counting positions from $1$ from the right. So for the example above, we have the correspondence:
$$sss\,{\bullet}\,{\bullet} \to 2\times1,
\qquad ss\,{\bullet}\,s\,{\bullet} \to 3\times1,
\qquad ss\,{\bullet}\,{\bullet}\,s \to 3\times2, \\
s\,{\bullet}\,ss\,{\bullet} \to 4\times1,
\qquad s\,{\bullet}\,s\,{\bullet}\,s \to 4\times2,
\qquad s\,{\bullet}\,{\bullet}\,ss \to 4\times3.
$$
As an additional consistency check, consider the permutations in $ss\,{\bullet}\,s\,{\bullet}$, which are $(1)(23)(45),(1)(24)(35),(1)(25)(34)$.
Summing all of these we get the expressions we wanted: ${5\brack2}=\sum_{i<j=1}^5 (i-1)(j-1)$.