section{I'm pretty cool}begin{tabular}{l l}
2009--present & company 1 \
2011--2012 & company 2
end{tabular}

2009 - present   company 1
2011 - 2012      company 2

2009 - present   company 1:
                   * editor
2011 - 2012      company 2
                   * judge
                   * jury
                   * executioner

documentclass{article}
usepackage{array}
makeatletter
newcolumntype{e}[1]{%--- Enumerated cells ---
   >{minipage[t]{linewidth}%
     NoHyper%                Hyperref adds a vertical space
     let\tabularnewline
     enumerate
        addtolength{rightskip}{0pt plus 50pt}% for raggedright
        setlength{itemsep}{-parsep}}%
   p{#1}%
   <{@finalstrut@arstrutboxendenumerate
     endNoHyper
     endminipage}}

newcolumntype{i}[1]{%--- Itemized cells ---
   >{minipage[t]{linewidth}%
        let\tabularnewline
        itemize
           addtolength{rightskip}{0pt plus 50pt}%
           setlength{itemsep}{-parsep}}%
   p{#1}%
   <{@finalstrut@arstrutboxenditemizeendminipage}}

AtBeginDocument{%
    @ifpackageloaded{hyperref}{}%
        {letNoHyperrelaxletendNoHyperrelax}}
makeatother

newlength{pcolwdth}
begin{document}
setlength{pcolwdth}{5cm}%
begin{tabular}{li{pcolwdth}}
2009--present & multicolumn{1}{p{pcolwdth}}{company 1} \
              & item editor                             \
2011--2012    & multicolumn{1}{p{pcolwdth}}{company 2} \
              & item judge
                item jury
                item executioner                        \
end{tabular}
end{document}

documentclass{article}
newcommand{nextitem}{parhspace*{labelsep}textbullethspace*{labelsep}}
begin{document}
thispagestyle{empty}
begin{tabular}{rp{3in}}
  2009--present & company 1
    nextitem editor \
  2011--2012 & company 2
    nextitem jury
    nextitem executioner
end{tabular}
end{document}

documentclass{article}
usepackage{array}
begin{document}
thispagestyle{empty}
begin{tabular}{l<{raggedright}p{3in}}
  2009--present & company 1
  begin{itemize}
  item editor
  end{itemize}
        2011--2012 & company 2
  begin{itemize}
  item jury
  item executioner
  end{itemize}
end{tabular}
end{document}

documentclass{article}
usepackage{parallel,enumitem}
setlist{label=*,leftmargin=0.31textwidth}
begin{document}
begin{Parallel}[v]{0.24textwidth}{0.74textwidth} % remove [v] if you don't need a vertical line
ParallelLText{noindent
2009--present
}
%
ParallelRText{%
noindent
Company 1
begin{enumerate}%[label=*,leftmargin=0.31textwidth] %defined by setlist in preamble
  item{editor}
end{enumerate}}
ParallelPar
bigskip
%---------------------
ParallelLText{noindent
2011--2012
}
%
ParallelRText{%
noindent
Company 1
begin{enumerate}%[label=*,leftmargin=0.31textwidth]
  item{Judge}
  item{Jury}
  item{Executioner}
end{enumerate}}
ParallelPar
bigskip
%---------------------
end{Parallel}

end{document}