No, this has not happened yet as of the time this answer was originally posted: until Jon Ericson, all former Community Managers who ceased to be employed at the company also ceased to be moderators after leaving.
Here are the CMs, past and present, ordered by period of service. This list does not count members of the support team as part of the group of CMs, although the answer is the same even if you do (at time of writing). (Note: current employees are not permitted to serve as volunteer moderators while employed, regardless of their job in the company.)
| Employee | Mod prior to hiring? | Currently employed? | Returned to moderator status? |
|---|---|---|---|
| Robert Cartaino | No | No (2010–2020) | - |
| Rebecca Chernoff ("rchern") | Yes (Web Applications) | No (2011–2013) | No |
| Shog9 | No | No (2011–2020) | - |
| Dori | Yes (Apple) | No (2011–2011) | No |
| HedgeMage | Yes (Parenting) | No (2011–2011) | No |
| Grace Note | Yes (Gaming) | Yes, but no longer a CM (2011–) | - |
| Aarthi | No | No (2011–2013) | - |
| Adam Lear | Yes (Stack Overflow, Software Engineering, Literature) | Yes, but no longer a CM (2012-) | - |
| Tim Post | Yes (Webmasters, Stack Overflow) | No (2013–2020) | Yes (Stack Overflow only) |
| Jon Ericson | Yes (Biblical Hermeneutics) | No (2013–2020) | Yes, now retired |
| Gabe | No | Yes, but no longer a CM (2013–) | - |
| Pops ("Popular Demand") | No | No (2013–2017) | - |
| Ana | No | No (2013–2018) | - |
| jmac | Yes (Workplace) | No (2014–2017) | No |
| hairboat ("abby hairboat") | No | No (2011–2021) | - |
| Nicolas Chabanovsky | No, but was founder of hashcode.ru which became ru.SO | Yes (2015–) | - |
| Taryn ("bluefeet") | Yes (Stack Overflow) | No (2015–2021) | No |
| Juan M | No | No (2015–2022) | - |
| JNat | Yes (Anime & Manga) | Yes (2015–) | - |
| Catija | Yes (Arts & Crafts, Interpersonal Skills) | Yes (2018–) | - |
| Cesar M | No | Yes (2019–) | - |
| Ayo | No | No (2021–2021) | - |
| Rosie | No | Yes (2021–) | - |
| Philippe | No | Yes (VP of Community) (2021–) | - |
| Slate | Yes (Puzzling, Literature) | Yes (2021–) | - |
| Charlotte | No | Yes (2021–) | - |
| V2Blast | Yes (Role-Playing Games) | Yes (2021–) | - |
| SpencerG | No | Yes (2021–) | - |
| Bella_Blue | No | Yes (2021–) | - |
| Salmon_of_Wisdom | No | Yes (2021–) | - |
| Berthold | No | Yes (2022–) | - |
| Dalmarus | No | Yes (2022–) | - |
An honorable mention goes to animuson, who was a community moderator (Stack Overflow.) animuson is not a CM, but they act in a very CM-like way as a member of the support team (2015–)
