In the below example is it possible to have the grid item's height be based off content and pushed to the top? I tried setting some grid-template-rows and grid-auto-flow but that doesn't seem to work either.
.wrapper {
  display: grid;
  grid-template-columns: repeat(4, 1fr);
  grid-auto-flow: dense;
  list-style: none;
  max-width: 500px;
}
.wrapper > li {
  border: 1px solid black;
}<ul class="wrapper">
  <li>
    <a href="#">Heading</a>
    <ul>
      <li><a href="#">Item 1</a></li>
      <li><a href="#">Item 2</a></li>
      <li><a href="#">Item 3</a></li>
      <li><a href="#">Item 4</a></li>
      <li><a href="#">Item 5</a></li>
    </ul>
  </li>
  <li>
    <a href="#">Heading</a>
    <ul>
      <li><a href="#">Item 1</a></li>
      <li><a href="#">Item 2</a></li>
      <li><a href="#">Item 3</a></li>
      <li><a href="#">Item 4</a></li>
    </ul>
  </li>
  <li>
    <a href="#">Heading</a>
    <ul>
      <li><a href="#">Item 1</a></li>
      <li><a href="#">Item 2</a></li>
    </ul>
  </li>
  <li>
    <a href="#">Heading</a>
    <ul>
      <li><a href="#">Item 1</a></li>
      <li><a href="#">Item 2</a></li>
    </ul>
  </li>
  <li>
    <a href="#">Heading</a>
    <ul>
      <li><a href="#">Item 1</a></li>
      <li><a href="#">Item 2</a></li>
    </ul>
  </li>
  <li>
    <a href="#">Heading</a>
    <ul>
      <li><a href="#">Item 1</a></li>
    </ul>
  </li>
  <li>
    <a href="#">Heading</a>
  </li>
</ul>
