\documentclass{article}
\usepackage{rotating}
\usepackage{tikz}
\usepackage{graphicx}
\usepackage{fontspec}
\usepackage{tocloft}
\usepackage{titletoc}
\usepackage{lipsum}
\setmainfont{LEMONMILK-Bold.otf}[Path=Assets/Fonts/]
\begin{document}
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\begin{titlepage}
\begin{tikzpicture}[remember picture,overlay]
\fill[color=black] (current page.north west) rectangle ++(5cm,-\paperheight);
\node[anchor=south west, text=white] at (current page.south west) {\hspace{1.5cm}\begin{turn}{90}
\resizebox{!}{35.5pt}{\hspace{0.17cm}Software Design Document}\end{turn}};
\end{tikzpicture}
\begin{flushright}
\vspace{7.5cm}
\Huge Title
\vspace{0.5cm}
\Large Subtitle (optional)
\vspace{8cm}
\normalsize Feb 30th, 2030
\end{flushright}
\end{titlepage}
\newpage
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%%%%%%%%%% LIST OF CONTENTS %%%%%%%%%%
\tableofcontents
\newpage
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%%%%%%%%%% CONTENT %%%%%%%%%%
\setmainfont{LEMONMILK-Bold.otf}[Path=Assets/Fonts/]
\section{Description}
\setmainfont{LEMONMILK-Regular.otf}[Path=Assets/Fonts/]
\lipsum[1-2]
\newpage
\setmainfont{LEMONMILK-Bold.otf}[Path=Assets/Fonts/]
\section{Development plan}
\setmainfont{LEMONMILK-Regular.otf}[Path=Assets/Fonts/]
\lipsum[2-4]
\newpage
\setmainfont{LEMONMILK-Bold.otf}[Path=Assets/Fonts/]
\section{Target Users}
\setmainfont{LEMONMILK-Regular.otf}[Path=Assets/Fonts/]
\lipsum[2-4]
\newpage
\setmainfont{LEMONMILK-Bold.otf}[Path=Assets/Fonts/]
\section{Features}
\setmainfont{LEMONMILK-Regular.otf}[Path=Assets/Fonts/]
\subsection{Feature 1}
\lipsum[2-4]
\subsection{Feature 2}
\lipsum[2-4]
\subsection{Feature 3}
\lipsum[2-4]
\newpage
\setmainfont{LEMONMILK-Bold.otf}[Path=Assets/Fonts/]
\section{Technologies}
\setmainfont{LEMONMILK-Regular.otf}[Path=Assets/Fonts/]
\subsection{Item 1}
\lipsum[2-4]
\subsection{Item 2}
\lipsum[2-4]
\subsection{Item 3}
\lipsum[2-4]
\newpage
\setmainfont{LEMONMILK-Bold.otf}[Path=Assets/Fonts/]
\section{Distribution Plan (optional)}
\setmainfont{LEMONMILK-Regular.otf}[Path=Assets/Fonts/]
\lipsum[2-4]
\newpage
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\end{document}
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