I managed to solve this with a rather nasty workaround, so I'm still looking for a better solution, but if anyone needs this for the future, I solved it like this:
<telerik:GridViewCheckBoxColumn Header="{Binding Resx.Confirmed}" DataMemberBinding="{Binding Confirmed}">
<telerik:GridViewCheckBoxColumn.GroupHeaderTemplate>
<DataTemplate>
<Label>
<Label.Style>
<Style TargetType="{x:Type Label}">
<Setter Property="Content" Value="{Binding DataContext.Resx.True, RelativeSource={RelativeSource AncestorType={x:Type UserControl}}}" />
<Style.Triggers>
<DataTrigger Binding="{Binding Group.Items[0].Confirmed}" Value="False">
<Setter Property="Content" Value="{Binding DataContext.Resx.False, RelativeSource={RelativeSource AncestorType={x:Type UserControl}}}" />
</DataTrigger>
</Style.Triggers>
</Style>
</Label.Style>
</Label>
</DataTemplate>
</telerik:GridViewCheckBoxColumn.GroupHeaderTemplate>
</telerik:GridViewCheckBoxColumn>