Can I license machines that are NOT Domain joined?

Short answer for PolicyPak Suite (On-Prem Edition): No.
Short answer for PolicyPak Cloud: Yes.

For PolicyPak Suite (On-Prem Edition), your delivery method (using Group Policy, SCCM, LanDesk, etc) requires that all computers must be domain joined.

All computers must be domain joined at least once and have the “knowledge” of what OU they’re in and get the PolicyPak license information first. Then they can go offline and PolicyPak Suite (On-Prem Edition) and its components will continue to work during the licensing period.

But at no time can computers which were NEVER domain joined participate with PolicyPak Suite (On-Prem Edition) or any of its components.

If you have non-domain joined machines, and you want to get settings to them (PolicyPak Application Manager, PolicyPak Preferences Manager, PolicyPak Admin Templates, or PolicyPak Security Settings) you need to use PolicyPak Cloud which can deliver all settings to non-domain joined machines.