To begin with, I noted that
$$ \begin{aligned} \displaystyle \sum_{r_1 = 1}^{r} r_1 &= \dfrac{1}{2} r (r+1) \quad &(1)\\ \displaystyle \sum_{r_2 = 1}^{r} \displaystyle \sum_{r_1 = 1}^{r_2} r_1 &= \dfrac{1}{6} r (r+1) (r+2). & \qquad(2) \end{aligned}$$ This led me to suggest the more general conjecture that $$ \begin{aligned} \displaystyle \sum_{r_n = 1}^{r} \displaystyle \sum_{r_{n-1} = 1}^{r_n} \cdots \displaystyle \sum_{r_2 = 1}^{r_3} \displaystyle \sum_{r_1 = 1}^{r_2} r_1 &= \dfrac{1}{(n+1)!} \prod_{k=0}^{n} (r+k) \\ &= \dfrac{1}{(n+1)!} \dfrac{(r+n)!}{(r-1)!} \qquad(\star) \end{aligned} $$
I believe that I've managed to successfully prove this using induction, but on the whole the process isn't very enlightening and given how "nice" the result is I'm led to believe that there's some more general insight here that I'm missing.
I've seen a link to the geometric interpretation of $ (1) $ by "pasting together" two copies of the sum to form a rectangle and I imagine the proof carries through analogously for $ (2) $ by forming a cuboid using 6 copies of the summation, but I'm not sure how to formalise this method of thinking (or indeed how to generalise it to higher dimensions). Of course this is just one particular thought I've had so any alternative proofs would also be welcome!
The essence is already encoded in the indices of the sums.
The number of summands given by the index range $$1\leq r_0\leq r_1\leq \cdots\leq r_n\leq r$$ is the number of ordered $(n+1)$-tupel $(r_0,\ldots,r_n)$ between $1$ and $r$ with repetition. This number is given by the binomial coefficient \begin{align*} \binom{(n+1)+r-1}{n+1}=\binom{n+r}{n+1} \end{align*} which corresponds to ($\star$) in OP's post.