\documentclass{article}
\usepackage{outlines}
\usepackage[shortlabels]{enumitem}
\setlist[enumerate,1]{label=\arabic*)}
\setlist[enumerate,2]{label=\alph*.}
\begin{document}
\begin{outline}[enumerate]
\1 The first bullet point which is numbered.
\2 The second one which has a letter.
\end{outline}
\begin{outline}[enumerate]
\1 Continue enumeration of the number.
\2 Start over enumeration of the letter.
\end{outline}
\end{document}