For brevity, let $A_n = \sum_{k=1}^{n}a_n$.
1. $\{a_n\}_{n\geq 1}\text{ infinitesimal}\Rightarrow\{A_n/n\}_{n\geq 1}\text{ infinitesimal}$.
This is kind of trivial: if a sequence is infinitesimal, it is infinitesimal on average, too.
For any $\varepsilon>0$, there is some $N_\varepsilon$ ensuring $|a_n|\leq\varepsilon$ as soon as $n\geq N_\varepsilon$.
It follows that if $n=kN_\varepsilon$ with $k>1$ we have
$$|A_n| \leq \left|\sum_{k=1}^{N_\varepsilon}a_n\right|+(k-1)N_\varepsilon \varepsilon $$
so $\frac{A_n}{n}$ is bounded by $2\varepsilon$ in absolute value as soon as $n$ is big enough. $\varepsilon$ is arbitrary and we are done.
We do not need the non-negativity of $\{a_n\}_{n\geq 1}$, just its bounded-ness, following from the $\text{infinitesimal}$ assumption.
2. $\{A_n/n\}_{n\geq 1}\text{ infinitesimal}\Rightarrow\{a_n\}_{n\geq 1}\text{ infinitesimal}$.
This is simply false, even with the assumption $a_n\in (0,1)$. It is enough to consider the sequence given by $a_n=\frac{1}{n}$ if $n$ is not a power of $2$ and $\frac{1}{2}$ if $n$ is a power of $2$. This sequence is infinitesimal on average but not infinitesimal tout court. This converse of 1. requires stronger assumptions on the behaviour of $\{a_n\}_{n\geq 1}$ or $\{A_n/n\}_{n\geq 1}$. Hardy's inequality gives a glance at the possible additional assumptions we may require to make 2. hold. As remarked by quasi in the comments, "$\{a_n\}_{n\geq 1}$ is convergent" is one of them, but "$\{A_n/n\}_{n\geq 1}\in\ell^p$ for some $p>1$" works just as well.